Organic & Biomolecular Chemistry最新文献

We report a gold-catalysed cyclisation of N-allenamides derived from 1- and 2-(2-aminoaryl)indoles, providing easy access to 5,6-dihydroindolo[1,2-a]quinoxalines and 6,11-dihydro-5H-indolo[3,2-c]quinolines. The reaction proceeds under mild conditions, tolerates diverse functional groups, and enables the synthesis of previously unexplored indole-fused heterocycles, whose versatility was demonstrated through selected post-functionalisation reactions.

An effective method for constructing thermodynamically unstable 1Z,4Z-dienes via Rh-catalysed cross-coupling of allylic gem-difluorides with tertiary Z-allylic alcohols has been developed. The fluoride elimination of the gem-difluoride propenes and β-Z-alkenyl elimination of the tertiary Z-allylic alcohols have been combined smoothly. This transformation furnishes a series of fluorinated (1Z,4Z)-dienes in moderate-to-high yields under mild conditions, exhibiting broad substrate scope, excellent functional group tolerance, and excellent chemo- and regioselectivity.

Expression of Concern for ‘Total synthesis of the natural product EBC-329’ by Raju S. Thombal and Vrushali H. Jadhav, Org. Biomol. Chem., 2015, 13, 9485–9491, https://doi.org/10.1039/C5OB01276G.

A rare strategy for three-component tandem benzyl-C(sp³)-H functionalization via thermally generated arynes with phenazine without a catalyst was developed for the first time. A series of novel fused N,N'-disubstituted dihydrophenazine derivatives were synthesized with excellent yield and high atomic utilization. Deuterium-labelling studies suggested that the formation of carboanion intermediates has a significant role in the reaction. Our data enrich the field of C(sp³)-H functionalization and promote the development of aryne chemistry.

In the past decade, 4-chloro-2H-chromene-3-carbaldehyde scaffolds (CCCS) have emerged as versatile precursors in modern organic synthesis. This review critically analyzes recent advancements in the chemical reactivity and synthetic accessibility of CCCS. We evaluate their pivotal role in developing potent agents against inflammation, cancer, and microbial resistance, while also addressing applications in energy sectors. By identifying the most efficient derivatives within each series, this work provides a strategic framework for leveraging CCCS in future pharmaceutical and materials science research.

Correction for ‘Asymmetric synthesis of isoindolines via a palladium-catalyzed enantioselective intramolecular oxidative aminoacetoxylation reaction’ by Dongyuan Ju et al., Org. Biomol. Chem., 2025, https://doi.org/10.1039/d5ob01595b.

Oxaboroles, five-membered boron-containing heterocycles, have emerged as an increasingly versatile framework in drug discovery and molecular design. Their significance stems from the unique Lewis acidity of the boron center, which enables reversible covalent interactions with biological targets. This property has led to the successful development of FDA-approved therapeutics such as tavaborole (antifungal) and crisaborole (anti-inflammatory), sparking widespread research interest. This review comprehensively summarizes the key advancements in the synthesis and application of oxaborole derivatives over the last decade. The synthetic methodologies are systematically categorized based on the principal starting materials, including alkynes, alkenes, aryl halides, aryl boronic acids, and oxaboranes. Emphasis is placed on the development of sustainable and efficient routes, such as photocatalytic, mechanochemical, and continuous-flow processes. Along with the synthesis, the review also covers the expanding applications of these compounds in different fields.

A new efficient and waste-free approach to synthesize (S)-Netarsudil, a blockbuster drug for the treatment of glaucoma and increased intraocular pressure (IOP), has been developed. It is based on the use of terephthalic dialdehyde as a commercially available starting compound and an asymmetric organocatalytic Michael reaction as the key step responsible for the creation of a stereogenic center with the required (S)-configuration. The advantages of the proposed methodology over the currently known one are the higher overall yield of the target drug, use of a reusable organocatalyst, mild and green reaction conditions, and the elimination of labor-intensive and time-consuming stages for the isolation of auxiliary groups.

The direct synthesis of γ-nitro alcohols, valuable precursors to 1,3-amino alcohols, from simple starting materials remains a challenge. Herein, we disclose a photoredox-catalyzed Giese reaction between (trimethylsilyl)methanol and nitroalkenes, operating under mild conditions to conveniently access a diverse array of γ-nitro alcohols. The synthetic utility of this protocol is demonstrated through its scalability and facile downstream conversion to valuable 1,3-amino alcohols. Mechanistic studies reveal that the reaction proceeds via a photoinduced radical Brook rearrangement followed by a Giese addition.

A visible-light-driven direct C–H alkylation of heterocycles using Cu@g-C₃N₄ heterojunctions as recyclable photocatalysts and alkylhydrazines as alkylating reagents was reported. This heterogeneous photocatalytic system can operate under additive-free and mild conditions to deliver an assortment of alkylated heterocycles in moderate to excellent yields, featuring high efficiency, broad substrate scope, easy scalability, excellent functional group tolerance, and exceptional catalyst recyclability.