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镍催化炔烃与有机硼酸和醛的芳基化反应以制备立体定向的烯丙醇。

Ni-catalyzed arylation of alkynes with organoboronic acids and aldehydes to access stereodefined allylic alcohols.

作者信息

Tao Si-Chen, Meng Fan-Cheng, Wang Tie, Zheng Yan-Long

机构信息

Tianjin Key Laboratory of Drug Targeting and Bioimaging, Life and Health Intelligent Research Institute, Tianjin University of Technology Tianjin 300384 P. R. China

出版信息

Chem Sci. 2023 Jan 20;14(8):2040-2045. doi: 10.1039/d2sc05894d. eCollection 2023 Feb 22.

Abstract

A new, efficient and practical method for the three-component arylative coupling of aldehydes, alkynes and arylboronic acids has been developed through nickel catalysis. This transformation provides diverse -selective tetrasubstituted allylic alcohols without the use of any aggressive oragnometallic nucleophiles or reductants. Moreover, benzylalcohols are viable coupling partners oxidation state manipulation and arylative coupling in one single catalytic cycle. This reaction features a direct and flexible approach for the preparation of stereodefined arylated allylic alcohols with broad substrate scope under mild conditions. The utility of this protocol is demonstrated through the synthesis of diverse biologically active molecular derivatives.

摘要

通过镍催化,开发了一种用于醛、炔烃和芳基硼酸三组分芳基化偶联的新型、高效且实用的方法。这种转化无需使用任何活性强的有机金属亲核试剂或还原剂,就能提供多种选择性的四取代烯丙醇。此外,苄醇在单个催化循环中是可行的偶联伙伴,可实现氧化态操纵和芳基化偶联。该反应具有一种直接且灵活的方法,可在温和条件下制备具有广泛底物范围的立体定向芳基化烯丙醇。通过合成多种生物活性分子衍生物证明了该方法的实用性。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1991/9945163/586427c68611/d2sc05894d-s1.jpg

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