Chemodivergent Synthesis of Multiborylalkanes via Deoxygenative Polyborylation of Silyl Enol Ethers.

IF 5 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2025-09-30 DOI:10.1021/acs.orglett.5c03751

Wenke Dong,Honghui Ma,Wanxiang Zhao

引用次数: 0

Abstract

A cobalt-catalyzed, chemodivergent deoxygenative polyborylation strategy for silyl enol ethers has been developed, enabling selective synthesis of 1,1,1-triborylalkanes, 1,1,3-triborylalkanes, 1,1-diborylalkenes, and 1,1-diborylalkanes. Specifically, deoxygenative borylation with B2pin2 affords 1,1,1-triborylalkanes, 1,1,3-triborylalkanes, and 1,1-diborylalkenes, while the use of HBpin favors 1,1-diborylalkane formation. This protocol offers mild reaction conditions, a broad substrate scope, and high functional group tolerance. The utility and practicality of this method were demonstrated through gram-scale reactions and various product transformations. Mechanistic investigations revealed that all processes are initiated via the cobalt-catalyzed dehydrogenative and deoxygenative borylation of silyl enol ethers.

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硅烯醚脱氧多硼化反应合成多硼烷的化学发散性研究。

开发了一种钴催化、化学发散的硅烯醇醚脱氧多硼化策略，可以选择性合成1,1,1-三硼烷、1,1,3-三硼烷、1,1-二硼烷和1,1-二硼烷。具体来说，与B2pin2的脱氧硼化反应生成1,1,1-三硼烷、1,1,3-三硼烷和1,1-二硼烷，而使用HBpin有利于生成1,1-二硼烷。该方案提供温和的反应条件，广泛的底物范围，和高官能团耐受性。通过克级反应和各种产物转化，证明了该方法的实用性和实用性。机理研究表明，所有过程都是通过钴催化的硅烯醇醚的脱氢和脱氧硼化反应引发的。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

Organic Letters 化学-有机化学

CiteScore

9.30

自引率

11.50%

发文量

1607

审稿时长

1.5 months

期刊介绍： Organic Letters invites original reports of fundamental research in all branches of the theory and practice of organic, physical organic, organometallic,medicinal, and bioorganic chemistry. Organic Letters provides rapid disclosure of the key elements of significant studies that are of interest to a large portion of the organic community. In selecting manuscripts for publication, the Editors place emphasis on the originality, quality and wide interest of the work. Authors should provide enough background information to place the new disclosure in context and to justify the rapid publication format. Back-to-back Letters will be considered. Full details should be reserved for an Article, which should appear in due course.