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对氟烷基取代烯烃的对映选择性钴催化氢硼化反应，以获得手性氟烷基硼酸酯。

Enantioselective Cobalt-Catalyzed Hydroboration of Fluoroalkyl-Substituted Alkenes to Access Chiral Fluoroalkylboronates.

机构信息

Department of Chemistry, National University of Singapore, 3 Science Drive 3, Singapore 117543, Singapore.

出版信息

J Am Chem Soc. 2022 Aug 24;144(33):15333-15338. doi: 10.1021/jacs.2c06488. Epub 2022 Aug 11.

DOI:10.1021/jacs.2c06488
PMID:35953077
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC9434995/
Abstract

Selective defluoroborylation and asymmetric hydroboration reactions of fluoroalkyl-substituted terminal alkenes with pinacolborane (HBpin) have been developed with cobalt catalysts generated from Co(acac) and bisphosphine ligands. A variety of fluoroalkyl-substituted terminal alkenes undergo this enantioselective hydroboration, affording the corresponding chiral alkylboronates containing fluoroalkyl-substituted stereogenic carbon centers with high enantioselectivity (up to 98% ). This asymmetric hydroboration provides a versatile foundation for the synthesis of a variety of chiral organofluorine compounds containing fluoroalkyl-substituted stereogenic carbon centers.

摘要

已经开发出了一种钴催化剂，由 Co(acac) 和双膦配体生成，用于氟烷基取代的末端烯烃与频哪醇硼烷（HBpin）的选择性脱氟硼化和不对称硼氢化反应。各种氟烷基取代的末端烯烃都能进行这种对映选择性的硼氢化反应，得到相应的手性烷基硼酸酯，其中含有氟烷基取代的手性碳原子中心，具有高对映选择性（高达 98%）。这种不对称硼氢化反应为合成各种含有氟烷基取代的手性碳原子中心的手性有机氟化合物提供了一个通用的基础。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c088/9434995/ff221866a052/ja2c06488_0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c088/9434995/3ef5c7210190/ja2c06488_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c088/9434995/cd7834da247b/ja2c06488_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c088/9434995/300cf0290381/ja2c06488_0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c088/9434995/ff221866a052/ja2c06488_0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c088/9434995/3ef5c7210190/ja2c06488_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c088/9434995/cd7834da247b/ja2c06488_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c088/9434995/300cf0290381/ja2c06488_0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c088/9434995/ff221866a052/ja2c06488_0005.jpg

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