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铜光催化的炔烃和烯烃硼氢化反应

Copper-Photocatalyzed Hydroboration of Alkynes and Alkenes.

作者信息

Zhong Mingbing, Gagné Yohann, Hope Taylor O, Pannecoucke Xavier, Frenette Mathieu, Jubault Philippe, Poisson Thomas

机构信息

Normandie Univ., INSA Rouen, UNIROUEN, CNRS, COBRA (UMR 6014), 76000, Rouen, France.

Département de Chimie, Université du Québec à Montréal, Case postal 8888, Succursale Centre-Ville, Montréal, Québec, H3C 3P8, Canada.

出版信息

Angew Chem Int Ed Engl. 2021 Jun 21;60(26):14498-14503. doi: 10.1002/anie.202101874. Epub 2021 May 17.

DOI:10.1002/anie.202101874
PMID:33780588
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC8252632/
Abstract

The photocatalytic hydroboration of alkenes and alkynes is reported. The use of newly-designed copper photocatalysts with B Pin permits the formation a boryl radical, which is used for hydroboration of a large panel of alkenes and alkynes. The hydroborated products were isolated in high yields, with excellent diastereoselectivities and a high functional group tolerance under mild conditions. The hydroboration reactions were developed under continuous flow conditions to demonstrate their synthetic utility. The reaction mechanism was studied and suggested an oxidation reaction between an in situ formed borate and the Cu-photocatalyst in its excited state for the boryl radical formation.

摘要

报道了烯烃和炔烃的光催化硼氢化反应。使用新设计的带有B Pin的铜光催化剂能够形成硼自由基，该自由基可用于多种烯烃和炔烃的硼氢化反应。在温和条件下，硼氢化产物以高产率分离得到，具有优异的非对映选择性和高官能团耐受性。硼氢化反应在连续流动条件下进行，以展示其合成实用性。对反应机理进行了研究，表明原位形成的硼酸盐与处于激发态的铜光催化剂之间发生氧化反应以形成硼自由基。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8bcc/8252632/8f27f4936b1a/ANIE-60-14498-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8bcc/8252632/38e090750fa4/ANIE-60-14498-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8bcc/8252632/f42b5f4782f3/ANIE-60-14498-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8bcc/8252632/707e33464213/ANIE-60-14498-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8bcc/8252632/8f27f4936b1a/ANIE-60-14498-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8bcc/8252632/38e090750fa4/ANIE-60-14498-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8bcc/8252632/f42b5f4782f3/ANIE-60-14498-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8bcc/8252632/707e33464213/ANIE-60-14498-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8bcc/8252632/8f27f4936b1a/ANIE-60-14498-g001.jpg

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