Sequential Conversion of Vinyl Triflates to 1,2-Disilanes via Technical Control of Magnesium and Calcium Reducibility Differences

IF 4.9 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2025-01-17 DOI:10.1021/acs.orglett.4c04321

Tianyuan Zhang, Shota Tahara, Takuto Negishi, Misaki Yoshizawa, Yusuke Igarashi, Hirofumi Maekawa

引用次数: 0

Abstract

Reductive direct substitution of α-arylvinyl triflates on the sp² carbon atom by magnesium in the presence of chlorosilane proceeded to give the corresponding α-silylstyrenes, which could not be reduced further, and the reaction completely stopped because the reduction potential of α-silylstyrenes lies out of the reducible field of magnesium. The subsequent reduction of α-silylstyrenes by calcium brought about the second introduction of another silyl group to the vicinal carbon atom to lead a selective and simple route to a variety of 1,2-disilanes from vinyl triflates by cooperative works of magnesium and calcium with different reduction potentiality.

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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.