Pub Date : 2024-11-01Epub Date: 2023-12-02DOI: 10.1016/j.gresc.2023.11.010
Yanyan Que , Wenli Lei , Yin Fang , Shuzhong He , Yang Chen
Allenes are a class of unsaturated compounds containing a propadiene structural moiety, exhibiting essential physiological, pharmacological, and various reactivities. Their (4 + 3) cycloaddition reaction has become an effective method for synthesizing seven-membered rings, especially for heterocycles. This method has been continuously improved and developed. Herein, we review the (4 + 3) cycloaddition of allenes, focusing on the developed methodologies and the outlook in this field from 2013 to 2023.
{"title":"Recent advances in (4 + 3) cycloaddition of allenes","authors":"Yanyan Que , Wenli Lei , Yin Fang , Shuzhong He , Yang Chen","doi":"10.1016/j.gresc.2023.11.010","DOIUrl":"10.1016/j.gresc.2023.11.010","url":null,"abstract":"<div><div>Allenes are a class of unsaturated compounds containing a propadiene structural moiety, exhibiting essential physiological, pharmacological, and various reactivities. Their (4 + 3) cycloaddition reaction has become an effective method for synthesizing seven-membered rings, especially for heterocycles. This method has been continuously improved and developed. Herein, we review the (4 + 3) cycloaddition of allenes, focusing on the developed methodologies and the outlook in this field from 2013 to 2023.</div></div>","PeriodicalId":12794,"journal":{"name":"Green Synthesis and Catalysis","volume":"5 4","pages":"Pages 270-276"},"PeriodicalIF":0.0,"publicationDate":"2024-11-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"138543705","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2024-11-01Epub Date: 2023-08-30DOI: 10.1016/j.gresc.2023.08.002
Linlin Shi , Tiantian Li , Wenjing Zhang , Weinan Hu , Xinju Zhu , Yixin Lu , Guang-Jian Mei
Visible-light induced direct C–H difluoromethylation of quinoxalinones with 2-((difluoromethyl)sulfonyl)benzo[d]thiazole has been developed for the first time. A broad range of quinoxalinones were well tolerated and reacted with difluorosulfone smoothly to give the corresponding products in moderate to good yields. Notably, no external photocatalyst or oxidant was required, which provides a practical and green protocol to access difluoromethylated quinoxalinones. Finally, the control experiments demonstrated a radical mechanism, and the density functional theory (DFT) calculations indicated the radicals were generated through the formation of an electron donor−acceptor (EDA) complex.
{"title":"Visible-light induced photocatalyst-free difluoromethylation of quinoxalinones with difluorosulfones","authors":"Linlin Shi , Tiantian Li , Wenjing Zhang , Weinan Hu , Xinju Zhu , Yixin Lu , Guang-Jian Mei","doi":"10.1016/j.gresc.2023.08.002","DOIUrl":"10.1016/j.gresc.2023.08.002","url":null,"abstract":"<div><div>Visible-light induced direct C–H difluoromethylation of quinoxalinones with 2-((difluoromethyl)sulfonyl)benzo[d]thiazole has been developed for the first time. A broad range of quinoxalinones were well tolerated and reacted with difluorosulfone smoothly to give the corresponding products in moderate to good yields. Notably, no external photocatalyst or oxidant was required, which provides a practical and green protocol to access difluoromethylated quinoxalinones. Finally, the control experiments demonstrated a radical mechanism, and the density functional theory (DFT) calculations indicated the radicals were generated through the formation of an electron donor−acceptor (EDA) complex.</div></div>","PeriodicalId":12794,"journal":{"name":"Green Synthesis and Catalysis","volume":"5 4","pages":"Pages 277-281"},"PeriodicalIF":0.0,"publicationDate":"2024-11-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"80415171","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2024-11-01Epub Date: 2024-05-06DOI: 10.1016/j.gresc.2024.04.008
Maolin Yang , Yukun Liu , Xin Qi , Yanhua Zhao , Xiao-Feng Wu
The development of catalytic carbonylation reactions has increased considerably. Although many reviews/chapters/books on carbonylation reactions have been published, summaries on cheap metal-catalyzed catalytic carbonylation reactions of aryl halides and other chemical bonds with high dissociation energy C–Y (Y = O, N, H) are still very rare. Focusing on green and sustainable chemistry, this review summarizes and discusses the achievements on carbonylative transformations of aryl halides (C(sp2)–X) and strong bonds C–Y (Y = O, N, H) based on non-expensive metal catalysts (Co, Mn, Mo, Ni, Fe, Cu), photochemical and electrochemical systems developed in recent decades.
{"title":"Carbonylative transformation of aryl halides and strong bonds via cheap metal catalysts and sustainable technologies","authors":"Maolin Yang , Yukun Liu , Xin Qi , Yanhua Zhao , Xiao-Feng Wu","doi":"10.1016/j.gresc.2024.04.008","DOIUrl":"10.1016/j.gresc.2024.04.008","url":null,"abstract":"<div><div>The development of catalytic carbonylation reactions has increased considerably. Although many reviews/chapters/books on carbonylation reactions have been published, summaries on cheap metal-catalyzed catalytic carbonylation reactions of aryl halides and other chemical bonds with high dissociation energy C–Y (Y = O, N, H) are still very rare. Focusing on green and sustainable chemistry, this review summarizes and discusses the achievements on carbonylative transformations of aryl halides (C(sp<sup>2</sup>)–X) and strong bonds C–Y (Y = O, N, H) based on non-expensive metal catalysts (Co, Mn, Mo, Ni, Fe, Cu), photochemical and electrochemical systems developed in recent decades.</div></div>","PeriodicalId":12794,"journal":{"name":"Green Synthesis and Catalysis","volume":"5 4","pages":"Pages 211-269"},"PeriodicalIF":0.0,"publicationDate":"2024-11-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141051230","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2024-11-01Epub Date: 2023-10-18DOI: 10.1016/j.gresc.2023.10.001
Yanhong Wang , Xinlei Zhou , Tao Zhang , Xinxin Ren , Wei Xu , Bin Wang , Weiwei Jin , Yu Xia , Chenjiang Liu , Yonghong Zhang
A metal-free visible-light-induced synthesis of aza-polycyclic aromatic hydrocarbons via cascade alkylation/cyclization of N-methacryloyl-2-phenylbenzimidazole was developed. The reaction was carried out with inactive alkanes and cyclic ethers as alkylation reagents, and phenanthrenequinone (PQ) as a direct hydrogen-atom transfer (HAT) photocatalyst. The desired products were obtained in moderate to good yields at room temperature under air.
{"title":"Visible-light-induced radical-cascade alkylation/cyclization of N-methacryloyl-2-phenylbenzimidazole: Access to benzoimidazo[2,1-a]isoquinolin-6(5H)-ones","authors":"Yanhong Wang , Xinlei Zhou , Tao Zhang , Xinxin Ren , Wei Xu , Bin Wang , Weiwei Jin , Yu Xia , Chenjiang Liu , Yonghong Zhang","doi":"10.1016/j.gresc.2023.10.001","DOIUrl":"10.1016/j.gresc.2023.10.001","url":null,"abstract":"<div><div>A metal-free visible-light-induced synthesis of aza-polycyclic aromatic hydrocarbons <em>via</em> cascade alkylation/cyclization of <em>N</em>-methacryloyl-2-phenylbenzimidazole was developed. The reaction was carried out with inactive alkanes and cyclic ethers as alkylation reagents, and phenanthrenequinone (PQ) as a direct hydrogen-atom transfer (HAT) photocatalyst. The desired products were obtained in moderate to good yields at room temperature under air.</div></div>","PeriodicalId":12794,"journal":{"name":"Green Synthesis and Catalysis","volume":"5 4","pages":"Pages 319-323"},"PeriodicalIF":0.0,"publicationDate":"2024-11-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"135851083","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2024-11-01Epub Date: 2023-11-14DOI: 10.1016/j.gresc.2023.11.003
Dangui Wang , Jinbei Yao , Wentao Zhang , Shuyue Zhang , Huaibin Yu , Laihu Peng , Weijun Yao , Zhifeng Dai , Guojiao Wu , Fangrui Zhong
C(sp2)-H amination represents an attractive approach for the synthesis of enamines, which is intrinsically associated with the challenge of controlling of stereochemistry and primarily relying on transition-metal catalysis. Herein, a metal-free C(sp2)-H amination of α-substituted styrenes has been achieved, leading to stereodivergent formation of both E- and Z-enamines in 50 %–97 % yield under mild conditions by using PhI(OAc)2 as a green oxidant and ortho-phenylenediamines as nitrogen source. Interestingly, the Z/E selectivity can be controlled readily by switching the reaction medium. E-isomers were formed preferentially in THF, whereas n-hexane favored the formation of Z-isomers. Preliminary mechanistic studies suggested that in situ formed ortho-benzoquinone diimides are the key intermediates, and there is a correlation between solvent polarity and stereoselectivity. This study enriches the chemical repertoire of ortho-benzoquinone diimides particularly with respect to sustainable amination.
{"title":"Solvent-controlled stereodivergent synthesis of E- and Z-enamines via metal-free formal C(sp2)-H amination of α-substituted styrenes","authors":"Dangui Wang , Jinbei Yao , Wentao Zhang , Shuyue Zhang , Huaibin Yu , Laihu Peng , Weijun Yao , Zhifeng Dai , Guojiao Wu , Fangrui Zhong","doi":"10.1016/j.gresc.2023.11.003","DOIUrl":"10.1016/j.gresc.2023.11.003","url":null,"abstract":"<div><div>C(sp<sup>2</sup>)-H amination represents an attractive approach for the synthesis of enamines, which is intrinsically associated with the challenge of controlling of stereochemistry and primarily relying on transition-metal catalysis. Herein, a metal-free C(sp<sup>2</sup>)-H amination of α-substituted styrenes has been achieved, leading to stereodivergent formation of both <em>E</em>- and <em>Z</em>-enamines in 50 %–97 % yield under mild conditions by using PhI(OAc)<sub>2</sub> as a green oxidant and <em>ortho</em>-phenylenediamines as nitrogen source. Interestingly, the <em>Z</em>/<em>E</em> selectivity can be controlled readily by switching the reaction medium. <em>E</em>-isomers were formed preferentially in THF, whereas <em>n</em>-hexane favored the formation of <em>Z</em>-isomers. Preliminary mechanistic studies suggested that in situ formed <em>ortho</em>-benzoquinone diimides are the key intermediates, and there is a correlation between solvent polarity and stereoselectivity. This study enriches the chemical repertoire of <em>ortho</em>-benzoquinone diimides particularly with respect to sustainable amination.</div></div>","PeriodicalId":12794,"journal":{"name":"Green Synthesis and Catalysis","volume":"5 4","pages":"Pages 324-328"},"PeriodicalIF":0.0,"publicationDate":"2024-11-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"135764107","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2024-11-01Epub Date: 2023-09-01DOI: 10.1016/j.gresc.2023.08.004
Wanjun Chen , Xinlong Yan , Lin Fan , Xu Guo , Jian Yang , Yiming Chen , Shaofang Zhou , Guodu Liu
The construction of chiral quaternary carbon stereocenters is a significant challenge in asymmetric synthesis. Catalytic synthesis of these structures with trisubstituted allylic alcohols is highly important. However, most of the reported methodologies required noble transition-metals. Herein we reported the first highly asymmetric stereoselective synthesis of cyclopentanes bearing chiral quaternary carbon stereocenters of trisubstituted allylic siloxanes by reductive cyclization of all carbon 1,6-alkynones with the non-noble nickel catalysis of Ni(cod)2 with P-chiral monophosphine ligand (S)-BIDIME. Various multi-substituted functionalized cyclopentanes were obtained in high yields (up to 96%), excellent enantioselectivities (up to >99% ee) and perfect stereoselectivities (>99:1 E/Z). Thirty-two examples were successfully established for this method. Clarified mechanism studies were investigated first time by React-IR and DFT calculations to understand and explain the ligand-control of excellent enantio-stereoselectivity. Gram-scale reaction and control experiments were carried out. A new reaction design was proposed for further application of this type of catalysis.
{"title":"Highly enantio-stereoselective Ni-catalyzed reductive cyclization to cyclopentanes with chiral quaternary centres of trisubstituted allylic siloxanes","authors":"Wanjun Chen , Xinlong Yan , Lin Fan , Xu Guo , Jian Yang , Yiming Chen , Shaofang Zhou , Guodu Liu","doi":"10.1016/j.gresc.2023.08.004","DOIUrl":"10.1016/j.gresc.2023.08.004","url":null,"abstract":"<div><div>The construction of chiral quaternary carbon stereocenters is a significant challenge in asymmetric synthesis. Catalytic synthesis of these structures with trisubstituted allylic alcohols is highly important. However, most of the reported methodologies required noble transition-metals. Herein we reported the first highly asymmetric stereoselective synthesis of cyclopentanes bearing chiral quaternary carbon stereocenters of trisubstituted allylic siloxanes by reductive cyclization of all carbon 1,6-alkynones with the non-noble nickel catalysis of Ni(cod)<sub>2</sub> with <em>P</em>-chiral monophosphine ligand <strong>(<em>S</em>)-BIDIME</strong>. Various multi-substituted functionalized cyclopentanes were obtained in high yields (up to 96%), excellent enantioselectivities (up to >99% <em>ee</em>) and perfect stereoselectivities (>99:1 <em>E/Z</em>). Thirty-two examples were successfully established for this method. Clarified mechanism studies were investigated first time by React-IR and DFT calculations to understand and explain the ligand-control of excellent enantio-stereoselectivity. Gram-scale reaction and control experiments were carried out. A new reaction design was proposed for further application of this type of catalysis.</div></div>","PeriodicalId":12794,"journal":{"name":"Green Synthesis and Catalysis","volume":"5 4","pages":"Pages 282-289"},"PeriodicalIF":0.0,"publicationDate":"2024-11-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"89588262","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2024-11-01Epub Date: 2023-11-28DOI: 10.1016/j.gresc.2023.11.008
Tao Liu , Jie Lin , Fangjun Xia , Zhenhui Xu , Xuying Xia , Wei Qian , Weihui Zhong , Dingguo Song , Fei Ling
Herein, we reported an efficient and straightforward method to realize desaturated β-C(sp3)-H sulfonylation and phosphonylation of cyclic amines driven by electrochemistry using catalytic amounts of CP2Fe as the redox mediator. This protocol which had good functional group compatibility, provided the desired enaminyl sulfone and enaminyl phosphine oxide products with high chemo- and regio-selectivity under mild conditions. Several mechanistic studies have suggested that cyclic amines underwent multiple single-electron oxidation and deprotonation processes, followed by a capture step involving either a sulfonyl radical or a phosphonyl radical, ultimately leading to the desired products.
{"title":"Electrochemical enabled desaturated β-C(sp3)-H sulfonylation and phosphonylation of cyclic amines","authors":"Tao Liu , Jie Lin , Fangjun Xia , Zhenhui Xu , Xuying Xia , Wei Qian , Weihui Zhong , Dingguo Song , Fei Ling","doi":"10.1016/j.gresc.2023.11.008","DOIUrl":"10.1016/j.gresc.2023.11.008","url":null,"abstract":"<div><div>Herein, we reported an efficient and straightforward method to realize desaturated <em>β</em>-C(sp<sup>3</sup>)-H sulfonylation and phosphonylation of cyclic amines driven by electrochemistry using catalytic amounts of CP<sub>2</sub>Fe as the redox mediator. This protocol which had good functional group compatibility, provided the desired enaminyl sulfone and enaminyl phosphine oxide products with high chemo- and regio-selectivity under mild conditions. Several mechanistic studies have suggested that cyclic amines underwent multiple single-electron oxidation and deprotonation processes, followed by a capture step involving either a sulfonyl radical or a phosphonyl radical, ultimately leading to the desired products.</div></div>","PeriodicalId":12794,"journal":{"name":"Green Synthesis and Catalysis","volume":"5 4","pages":"Pages 297-302"},"PeriodicalIF":0.0,"publicationDate":"2024-11-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"138512304","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2024-11-01Epub Date: 2023-10-21DOI: 10.1016/j.gresc.2023.10.003
Chao Xu , Yingkun Luo , Shengtong Niu , Fan Gong , Shouang Lan , Benlong Luo , Jinggong Liu , Shuang Yang , Xinqiang Fang
Ethers are among the most important chemicals in organic synthesis, the pharmaceutical industry, agrochemical production, and material science. C–O bond formation via substitution is one of the most widely used strategies for ether formation. However, known methods usually employ transition-metal and bases to facilitate the process. In this work, we describe the base- and transition-metal-free ether formation via alcohol and phenol-participated substitution. The protocol allows access to a large number of ethers with enyne functional moieties, and features mild reaction conditions, high efficiency, and good regio- and stereoselectivities. The reaction could be readily scaled up, and the products could be used in a range of further transformations.
{"title":"Transition-metal and base-free ether synthesis via alcohol-participated yne-allylic substitution","authors":"Chao Xu , Yingkun Luo , Shengtong Niu , Fan Gong , Shouang Lan , Benlong Luo , Jinggong Liu , Shuang Yang , Xinqiang Fang","doi":"10.1016/j.gresc.2023.10.003","DOIUrl":"10.1016/j.gresc.2023.10.003","url":null,"abstract":"<div><div>Ethers are among the most important chemicals in organic synthesis, the pharmaceutical industry, agrochemical production, and material science. C–O bond formation via substitution is one of the most widely used strategies for ether formation. However, known methods usually employ transition-metal and bases to facilitate the process. In this work, we describe the base- and transition-metal-free ether formation <em>via</em> alcohol and phenol-participated substitution. The protocol allows access to a large number of ethers with enyne functional moieties, and features mild reaction conditions, high efficiency, and good regio- and stereoselectivities. The reaction could be readily scaled up, and the products could be used in a range of further transformations.</div></div>","PeriodicalId":12794,"journal":{"name":"Green Synthesis and Catalysis","volume":"5 4","pages":"Pages 303-309"},"PeriodicalIF":0.0,"publicationDate":"2024-11-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"136010199","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2024-11-01Epub Date: 2023-10-18DOI: 10.1016/j.gresc.2023.10.002
Jingjing Wang , Feng Li , Kai Liu , Chong Li , Sheng Cao , Yuxiang Wu , Yongjun Yuan , Fei Teng , Teng Wang , Yao Zhou
We first describe a photoinduced decatungstate-catalyzed direct coupling of cycloalkanes and cyclic aldimines. The desired products were generated in moderate to good yields with wide substrate scope under mild reaction conditions. The mechanistic study revealed a radical process. In addition, the usefulness of the reaction in organic synthesis was proved by the scale-up synthesis as well as the late-stage modification of drug-like molecules.
{"title":"Photoinduced decatungstate-catalyzed direct coupling of cycloalkanes and cyclic aldimines","authors":"Jingjing Wang , Feng Li , Kai Liu , Chong Li , Sheng Cao , Yuxiang Wu , Yongjun Yuan , Fei Teng , Teng Wang , Yao Zhou","doi":"10.1016/j.gresc.2023.10.002","DOIUrl":"10.1016/j.gresc.2023.10.002","url":null,"abstract":"<div><div>We first describe a photoinduced decatungstate-catalyzed direct coupling of cycloalkanes and cyclic aldimines. The desired products were generated in moderate to good yields with wide substrate scope under mild reaction conditions. The mechanistic study revealed a radical process. In addition, the usefulness of the reaction in organic synthesis was proved by the scale-up synthesis as well as the late-stage modification of drug-like molecules.</div></div>","PeriodicalId":12794,"journal":{"name":"Green Synthesis and Catalysis","volume":"5 4","pages":"Pages 315-318"},"PeriodicalIF":0.0,"publicationDate":"2024-11-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"135852345","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2024-11-01Epub Date: 2023-07-26DOI: 10.1016/j.gresc.2023.07.004
Pu-Zhang Zi , Quan-Hong Zhao , Zhan-Cai Ma , Xiao-Lin Ren , Xing-Bang Liu , Yi-Wei Qiao , Lin-Wen Wei , Song Liu , Yuan Huang
The incorporation of additional Csp3 atoms into candidate drugs may enhance their pharmacological properties. Nevertheless, it remains challenging to construct desired Csp3-Csp3 bonds efficiently and practically. The present article reports a novel Csp3-Csp3 bond-forming reaction of 2-aryl/alkyl substituted aziridines with gem-diborylalkanes under tranisiton metal free conditions. A wide range of γ-gem-diboronate esters substituted amines can be accessed in good yield and regioselectivity. The results demonstrated that various aziridines could react with gem-diborylalkanes in the presence of LiTMP as the base within 15 min at ambient temperature.
{"title":"Transition metal-free Csp3-Csp3 bond-forming reactions of N-tosylaziridines and gem-diborylalkanes","authors":"Pu-Zhang Zi , Quan-Hong Zhao , Zhan-Cai Ma , Xiao-Lin Ren , Xing-Bang Liu , Yi-Wei Qiao , Lin-Wen Wei , Song Liu , Yuan Huang","doi":"10.1016/j.gresc.2023.07.004","DOIUrl":"10.1016/j.gresc.2023.07.004","url":null,"abstract":"<div><div>The incorporation of additional Csp<sup>3</sup> atoms into candidate drugs may enhance their pharmacological properties. Nevertheless, it remains challenging to construct desired Csp<sup>3</sup>-Csp<sup>3</sup> bonds efficiently and practically. The present article reports a novel Csp<sup>3</sup>-Csp<sup>3</sup> bond-forming reaction of 2-aryl/alkyl substituted aziridines with <em>gem</em>-diborylalkanes under tranisiton metal free conditions. A wide range of <em>γ</em>-<em>gem</em>-diboronate esters substituted amines can be accessed in good yield and regioselectivity. The results demonstrated that various aziridines could react with <em>gem</em>-diborylalkanes in the presence of LiTMP as the base within 15 min at ambient temperature.</div></div>","PeriodicalId":12794,"journal":{"name":"Green Synthesis and Catalysis","volume":"5 4","pages":"Pages 329-333"},"PeriodicalIF":0.0,"publicationDate":"2024-11-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"123572670","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
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