Nan Wang, Xia Chen, Chun-Yan Liu, Zhi-Ying Feng, Ming Bao, Xiao-Yu Zhou
The strained C−N bond of N-phenyl-N-tosylfluoroacetamides is activated via transition-metal-free nucleophilic addition pathway by employing suitable nucleophilic reagents, such as indoles, indolines, aryl amines and carboxylic acids. Based on this, two efficient and convenient approaches are developed for the synthesis of amides by utilizing divergent fragments of N-phenyl-N-tosylfluoroacetamides in this paper. The reaction of nitrogen-containing compounds and carboxylic acids with N-phenyl-N-tosylfluoroacetamides proceeded smoothly in the presence of base to provide diverse fluoroacetamides and N-tosylamides in satisfactory to excellent yields. N-Phenyl-N-tosylfluoroacetamides served as integrated reagents to provide either fluoroacetyl or amine source depending on what they react with. The protocols can be amenable to scale up. Various groups, including the synthetically useful functional groups Br, NO2, OH and CO2Me, were tolerated well under the current reaction conditions.
采用合适的亲核试剂，如吲哚、吲哚、芳基胺和羧酸，通过无过渡金属的亲核加成途径激活N-苯基-N-甲基氟乙酰胺的应变C−N键。在此基础上，本文开发了两种高效便捷的利用n -苯基- n -甲基氟乙酰胺分散片段合成酰胺的方法。在碱的存在下，含氮化合物和羧酸与n-苯基- n-甲酰基氟乙酰胺的反应顺利进行，得到了多种氟乙酰胺和n-甲酰基酰胺，产率令人满意。n -苯基- n -甲基氟乙酰胺作为集成试剂，根据它们与什么反应提供氟乙酰基或胺源。这些协议可以扩大规模。各种基团，包括合成有用的官能团Br、NO2、OH和CO2Me，在当前的反应条件下都能很好地耐受。
{"title":"Divergent Transformations of N-Phenyl-N-tosylfluoroacetamides to Amides and Imides (N-Tosylamides)","authors":"Nan Wang, Xia Chen, Chun-Yan Liu, Zhi-Ying Feng, Ming Bao, Xiao-Yu Zhou","doi":"10.1039/d6qo00069j","DOIUrl":"https://doi.org/10.1039/d6qo00069j","url":null,"abstract":"The strained C−N bond of N-phenyl-N-tosylfluoroacetamides is activated via transition-metal-free nucleophilic addition pathway by employing suitable nucleophilic reagents, such as indoles, indolines, aryl amines and carboxylic acids. Based on this, two efficient and convenient approaches are developed for the synthesis of amides by utilizing divergent fragments of N-phenyl-N-tosylfluoroacetamides in this paper. The reaction of nitrogen-containing compounds and carboxylic acids with N-phenyl-N-tosylfluoroacetamides proceeded smoothly in the presence of base to provide diverse fluoroacetamides and N-tosylamides in satisfactory to excellent yields. N-Phenyl-N-tosylfluoroacetamides served as integrated reagents to provide either fluoroacetyl or amine source depending on what they react with. The protocols can be amenable to scale up. Various groups, including the synthetically useful functional groups Br, NO2, OH and CO2Me, were tolerated well under the current reaction conditions.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"32 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2026-02-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"147279542","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Metal-free βand Z-selective hydrocyanation of terminal ynamides using TMSCN and TBAF is described. The transformation proceeds with excellent regio-and stereoselectivity, delivering exclusively Z-configured tertiary enamides. Treatment with TMSOTf promotes clean Z to E isomerization. Simultaneous activation of the nitrile moiety by TMSOTf in the presence of an internal nucleophile induces intramolecular cyclization, yielding piperidine frameworks. The reaction accommodates a range of nucleophiles, enabling the synthesis of structurally diverse and previously inaccessible heterocyclic scaffolds.
{"title":"β-and Z-Selective Metal-Free Cyanation of Ynamides: A Direct Approach to Piperidines Fused to Arenes","authors":"Dorian Schutz, Wenwen Yang, Laurence Miesch","doi":"10.1039/d6qo00022c","DOIUrl":"https://doi.org/10.1039/d6qo00022c","url":null,"abstract":"Metal-free βand Z-selective hydrocyanation of terminal ynamides using TMSCN and TBAF is described. The transformation proceeds with excellent regio-and stereoselectivity, delivering exclusively Z-configured tertiary enamides. Treatment with TMSOTf promotes clean Z to E isomerization. Simultaneous activation of the nitrile moiety by TMSOTf in the presence of an internal nucleophile induces intramolecular cyclization, yielding piperidine frameworks. The reaction accommodates a range of nucleophiles, enabling the synthesis of structurally diverse and previously inaccessible heterocyclic scaffolds.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"14 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2026-02-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"147279582","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Andrea Chaves-Pouso, Andrés Manuel Álvarez Constantino, Patricia Gomez Roibás, Martín Fañanás-Mastral
Chiral α,γ-substituted allyl boron reagents are valuable tools in organic synthesis. However, asymmetric catalytic strategies for synthesising this type of compounds bearing a stereodefined alkenyl chloride are underdeveloped. Here we report a copper-catalyzed enantioselective borylation of allylic gem-dichlorides that provides optically active allylic boronates bearing an (E)-configured alkenyl chloride with high levels of enantioselectivity and E-selectivity. These enantioenriched allyl boronates serve as versatile building blocks for different stereospecific reactions, including their conversion into chiral propargyl alcohols and the diastereoselective addition to ketones to afford enantioenriched allylic chlorohydrins. DFT calculations provide mechanistic insight, revealing key noncovalent interactions that rationalize the observed stereocontrol. This study expands the synthetic utility of allylic boronates and offers a mechanistically informed approach to asymmetric catalysis involving gem-dichloride substrates.
{"title":"Enantioselective Synthesis of Allylic Boronates bearing a Stereodefined (E)-Alkenyl Chloride by Cu-Catalyzed Borylation of Allylic gem-Dichlorides","authors":"Andrea Chaves-Pouso, Andrés Manuel Álvarez Constantino, Patricia Gomez Roibás, Martín Fañanás-Mastral","doi":"10.1039/d6qo00061d","DOIUrl":"https://doi.org/10.1039/d6qo00061d","url":null,"abstract":"Chiral α,γ-substituted allyl boron reagents are valuable tools in organic synthesis. However, asymmetric catalytic strategies for synthesising this type of compounds bearing a stereodefined alkenyl chloride are underdeveloped. Here we report a copper-catalyzed enantioselective borylation of allylic gem-dichlorides that provides optically active allylic boronates bearing an (E)-configured alkenyl chloride with high levels of enantioselectivity and E-selectivity. These enantioenriched allyl boronates serve as versatile building blocks for different stereospecific reactions, including their conversion into chiral propargyl alcohols and the diastereoselective addition to ketones to afford enantioenriched allylic chlorohydrins. DFT calculations provide mechanistic insight, revealing key noncovalent interactions that rationalize the observed stereocontrol. This study expands the synthetic utility of allylic boronates and offers a mechanistically informed approach to asymmetric catalysis involving gem-dichloride substrates.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"2 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2026-02-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"147279581","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
A one-pot synthesis of 1,2-disubstituted multifunctional benzimidazole derivatives starting from N-Allyl Ynamides and o-Haloanilines has been introduced. The mechanistic study suggests that the reaction proceeds via a Pd-catalyzed nucleophilic addition of N-allyl ynamides to the amino group of the o-haloanilines to form a amidine intermediate, followed by Cu-catalyzed intramolecular cyclization. The reaction could also be performed on a multi-gram scale with the same efficiency.
{"title":"Palladium/copper bimetallic system-catalyzed cascade cyclization of N-allyl Ynamides and o-haloanilines: access to multifunctional benzimidazoles","authors":"Yi-Yun Zhang, xuheng yang, Ai-Ming Wen, Fang Wang, Jian Huang, Jianfang Wang, Cheng-an Tao","doi":"10.1039/d6qo00038j","DOIUrl":"https://doi.org/10.1039/d6qo00038j","url":null,"abstract":"A one-pot synthesis of 1,2-disubstituted multifunctional benzimidazole derivatives starting from N-Allyl Ynamides and o-Haloanilines has been introduced. The mechanistic study suggests that the reaction proceeds via a Pd-catalyzed nucleophilic addition of N-allyl ynamides to the amino group of the o-haloanilines to form a amidine intermediate, followed by Cu-catalyzed intramolecular cyclization. The reaction could also be performed on a multi-gram scale with the same efficiency.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"2 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2026-02-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"147279958","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
The influence of the aromaticity, diradical character and strain on the reactivity of Group 14 heavier 1,4-dimetallabenzenes (E = Si, Ge, Sn) has been investigated using quantum-chemical calculations. To this end, the activation reactions of small molecules (dihydrogen and acetylene) promoted by these species have been investigated. It is found that the lighter systems (E = Si and Ge) are significantly more reactive than their 1,4-distannabenzene analogue, despite the latter exhibiting a larger diradical character. According to the Activation Strain Model of reactivity, the reduced reactivity of the heaviest species is directly related to its highly bent, chair-like equilibrium geometry, which must undergo substantial deformation (in comparison with its lighter congeners) to reach the corresponding transition state geometry.
{"title":"Group 14 heavier 1,4-dimetallabenzenes: Influence of Aromaticity, Open-Shell Character and Strain on Small Molecule Activation","authors":"Daniel Gónzalez-Pinardo, Israel Fernandez","doi":"10.1039/d6qo00006a","DOIUrl":"https://doi.org/10.1039/d6qo00006a","url":null,"abstract":"The influence of the aromaticity, diradical character and strain on the reactivity of Group 14 heavier 1,4-dimetallabenzenes (E = Si, Ge, Sn) has been investigated using quantum-chemical calculations. To this end, the activation reactions of small molecules (dihydrogen and acetylene) promoted by these species have been investigated. It is found that the lighter systems (E = Si and Ge) are significantly more reactive than their 1,4-distannabenzene analogue, despite the latter exhibiting a larger diradical character. According to the Activation Strain Model of reactivity, the reduced reactivity of the heaviest species is directly related to its highly bent, chair-like equilibrium geometry, which must undergo substantial deformation (in comparison with its lighter congeners) to reach the corresponding transition state geometry.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"57 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2026-02-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"147279540","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
This study employs density functional theory (DFT) calculations to elucidate the mechanism and alkali metal-dependent reactivity in the Ni0-catalyzed C(sp2)–F bond activation of fluoronaphthalenes, assisted by lithium acetylides. The results reveal that the energy barrier for C(sp2)–F bond activation initiated by the acetylide carbanion is 30.1 kcal mol−1, significantly higher than that (18.5 kcal mol−1) for the ethide carbanion-initiated one, due to the notably weaker nucleophilicity of the acetylide carbanion. Interestingly, the reaction between lithium acetylides and the pre-catalyst Ni0(cod)2 generates a Ni0(acetylide carbanion)-ate complex, in which high nucleophilicity is localized at the Ni0-center. Significantly, the energy barrier for C(sp2)–F bond activation catalyzed by the Ni0(acetylide carbanion)-ate complex via an inner-sphere nucleophilic aromatic substitution (SNAr) pathway is considerably lowered to 25.3 kcal mol−1. Theoretical analysis clarifies that the distinct reactivity of the ate complex stems from coordination of the acetylide carbanion to the Ni0 center, with strong Li⋯F interactions serving as a key driving force to stabilize the transition state. This work provides a comprehensive insight into transition metal-catalyzed C–F bond activation with the assistance of an acetylide carbanion, which is expected to offer a theoretical perspective for the rational design of C–F functionalization strategies.
{"title":"Theoretical investigation on the mechanism of Ni0(acetylide carbanion)-ate complex-catalyzed C(sp2)–F bond activation and the origin of the counterion effect on reactivity","authors":"Xiao-Xia You, Ling-Qi Meng, Xu Liu, Li-Li Wang, Xin-Cheng Xu, Rong-Lin Zhong, Zhong-Min Su","doi":"10.1039/d5qo01757b","DOIUrl":"https://doi.org/10.1039/d5qo01757b","url":null,"abstract":"This study employs density functional theory (DFT) calculations to elucidate the mechanism and alkali metal-dependent reactivity in the Ni<small><sup>0</sup></small>-catalyzed C(sp<small><sup>2</sup></small>)–F bond activation of fluoronaphthalenes, assisted by lithium acetylides. The results reveal that the energy barrier for C(sp<small><sup>2</sup></small>)–F bond activation initiated by the acetylide carbanion is 30.1 kcal mol<small><sup>−1</sup></small>, significantly higher than that (18.5 kcal mol<small><sup>−1</sup></small>) for the ethide carbanion-initiated one, due to the notably weaker nucleophilicity of the acetylide carbanion. Interestingly, the reaction between lithium acetylides and the pre-catalyst Ni<small><sup>0</sup></small>(cod)<small><sub>2</sub></small> generates a Ni<small><sup>0</sup></small>(acetylide carbanion)-ate complex, in which high nucleophilicity is localized at the Ni<small><sup>0</sup></small>-center. Significantly, the energy barrier for C(sp<small><sup>2</sup></small>)–F bond activation catalyzed by the Ni<small><sup>0</sup></small>(acetylide carbanion)-ate complex <em>via</em> an inner-sphere nucleophilic aromatic substitution (S<small><sub>N</sub></small>Ar) pathway is considerably lowered to 25.3 kcal mol<small><sup>−1</sup></small>. Theoretical analysis clarifies that the distinct reactivity of the ate complex stems from coordination of the acetylide carbanion to the Ni<small><sup>0</sup></small> center, with strong Li⋯F interactions serving as a key driving force to stabilize the transition state. This work provides a comprehensive insight into transition metal-catalyzed C–F bond activation with the assistance of an acetylide carbanion, which is expected to offer a theoretical perspective for the rational design of C–F functionalization strategies.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"13 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2026-02-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"147279960","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Despite their simple 10π aromatic nature and considerable functional potential, the chemistry of 5/5-fused N-heteroaromatic systems remains underdeveloped. Herein, we report a general strategy for accessing 1H-pyrrolo[1,2-b]pyrazoles, a largely unexplored “orphan” class of heterocycles. The methodology features the generation of pyrazolium ylides followed by [3+2] cycloaddition with alkynes under mild conditions, and a subsequent oxidative aromatization step that effectively suppresses undesired ring-opening and excessive addition pathways. The substrate scope demonstrates broad functional-group tolerance and accommodates diverse substitution patterns. Combined experimental and computational studies indicate a stepwise cycloaddition mechanism, the involvement of intrinsically unstable cycloadducts, and the presence of competing pathways that render the chemoselectivity highly sensitive to subtle changes in reaction conditions. Finally, downstream derivatization highlights the utility of the 5/5-fused framework as a versatile platform for constructing more structurally complex and/or functionally enriched molecules.
{"title":"Pyrazolium-Ylide [3+2] Cycloaddition/Oxidative Aromatization for the Construction of 1H-pyrrolo[1,2-b]pyrazoles","authors":"Motohiro Yasui, Tatsuya Tsumori, Masato Morita, Shigeyuki Yamada, Tsutomu Konno","doi":"10.1039/d6qo00070c","DOIUrl":"https://doi.org/10.1039/d6qo00070c","url":null,"abstract":"Despite their simple 10π aromatic nature and considerable functional potential, the chemistry of 5/5-fused N-heteroaromatic systems remains underdeveloped. Herein, we report a general strategy for accessing 1<em>H</em>-pyrrolo[1,2-<em>b</em>]pyrazoles, a largely unexplored “orphan” class of heterocycles. The methodology features the generation of pyrazolium ylides followed by [3+2] cycloaddition with alkynes under mild conditions, and a subsequent oxidative aromatization step that effectively suppresses undesired ring-opening and excessive addition pathways. The substrate scope demonstrates broad functional-group tolerance and accommodates diverse substitution patterns. Combined experimental and computational studies indicate a stepwise cycloaddition mechanism, the involvement of intrinsically unstable cycloadducts, and the presence of competing pathways that render the chemoselectivity highly sensitive to subtle changes in reaction conditions. Finally, downstream derivatization highlights the utility of the 5/5-fused framework as a versatile platform for constructing more structurally complex and/or functionally enriched molecules.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"320 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2026-02-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"146231043","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
A Pd(PPh3)4-catalyzed regioselective C–H para allylation process was developed for the reaction of N,N-dialkylanilines with vinyl benzoxazinanones. Such transformation demonstrated a novel application of vinyl benzoxazinanone reagents, allowing for the introduction of an alkenyl group exclusively to the para position of aniline derivatives. As a result, a series of N,N-dialkylaniline derivatives with para allyl type substitutions were synthesized with excellent regioselectivities (E:Z ratio >19:1).
{"title":"Pd(PPh3)4-Catalyzed Regioselective C–H para-Allylation of N,N-Dialkylanilines using Vinyl Benzoxazinanones","authors":"Lu Pei, Xiaolin Liu, Ding-Jun Zhang, Hui-Hong Tian, Ling-Dan Zhu, Bangguo Wei","doi":"10.1039/d6qo00093b","DOIUrl":"https://doi.org/10.1039/d6qo00093b","url":null,"abstract":"A Pd(PPh3)4-catalyzed regioselective C–H para allylation process was developed for the reaction of N,N-dialkylanilines with vinyl benzoxazinanones. Such transformation demonstrated a novel application of vinyl benzoxazinanone reagents, allowing for the introduction of an alkenyl group exclusively to the para position of aniline derivatives. As a result, a series of N,N-dialkylaniline derivatives with para allyl type substitutions were synthesized with excellent regioselectivities (E:Z ratio >19:1).","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"8 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2026-02-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"146231044","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Boryl-substituted cyclobutanes have emerged as valuable building blocks that merge the structural rigidity and strainenabled reactivity of four-membered rings with the versatile synthetic utility of organoboron chemistry. Here, the recent advances in the synthesis of boryl-substituted cyclobutanes, a class of strained, sp³-rich building blocks that combine the structural rigidity of cyclobutanes with the exceptional versatility of organoboron chemistry, have been summarized. Emphasis is placed on strategies that exploit boronate complex reactivity and 1,2-migration processes to overcome the inherent challenges associated with four-membered ring formation. Thermal, photochemical, and transition-metalcatalysed approaches are discussed, highlighting how strain-release, radical polar crossover, and σ-bond activation enable efficient and stereocontrolled cyclobutane construction. Key mechanistic insights that govern selectivity and reactivity also have been outlined across diverse platforms.2.
{"title":"Advances in the Construction of Boryl Cyclobutanes","authors":"Kanak Kanti Das, Sutapa Dey","doi":"10.1039/d6qo00008h","DOIUrl":"https://doi.org/10.1039/d6qo00008h","url":null,"abstract":"Boryl-substituted cyclobutanes have emerged as valuable building blocks that merge the structural rigidity and strainenabled reactivity of four-membered rings with the versatile synthetic utility of organoboron chemistry. Here, the recent advances in the synthesis of boryl-substituted cyclobutanes, a class of strained, sp³-rich building blocks that combine the structural rigidity of cyclobutanes with the exceptional versatility of organoboron chemistry, have been summarized. Emphasis is placed on strategies that exploit boronate complex reactivity and 1,2-migration processes to overcome the inherent challenges associated with four-membered ring formation. Thermal, photochemical, and transition-metalcatalysed approaches are discussed, highlighting how strain-release, radical polar crossover, and σ-bond activation enable efficient and stereocontrolled cyclobutane construction. Key mechanistic insights that govern selectivity and reactivity also have been outlined across diverse platforms.2.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"181 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2026-02-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"146231042","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Shengchen Wei, Yingjie Peng, Dan Shi, Xiang-Zhao Zhu, Songhua Chen, Lili Xie, Yuanming Li
This work presents the first modular synthesis method for Acepleiadylene derivatives which were synthesized through Suzuki coupling of biphenyl compounds with acenaphthenylboronic acid 1 followed by 2,3-dichloro-5,6-dicyano-1,4benzoquinone (DDQ) oxidation. Through the control of functional blocks, the manipulation of the structure of Acepleiadylene derivatives was achieved, which in turn different photoelectric properties. Modification and π-extension of APD were accomplished at the 5, 6, 7, and 8 positions. A comprehensive investigation of their structural, photophysical, and electronic properties was studied by experiment and theoretical calculations.
{"title":"A Modular Approach toward 5,6,7,8-functionalized Acepleiadylene derivatives","authors":"Shengchen Wei, Yingjie Peng, Dan Shi, Xiang-Zhao Zhu, Songhua Chen, Lili Xie, Yuanming Li","doi":"10.1039/d5qo01765c","DOIUrl":"https://doi.org/10.1039/d5qo01765c","url":null,"abstract":"This work presents the first modular synthesis method for Acepleiadylene derivatives which were synthesized through Suzuki coupling of biphenyl compounds with acenaphthenylboronic acid 1 followed by 2,3-dichloro-5,6-dicyano-1,4benzoquinone (DDQ) oxidation. Through the control of functional blocks, the manipulation of the structure of Acepleiadylene derivatives was achieved, which in turn different photoelectric properties. Modification and π-extension of APD were accomplished at the 5, 6, 7, and 8 positions. A comprehensive investigation of their structural, photophysical, and electronic properties was studied by experiment and theoretical calculations.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"128 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2026-02-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"146231189","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
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