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Regioselective Silylations of Propargyl and Allyl Pivalates through Ca-Promoted Reductive C(sp3)–O Bond Cleavage
Organic Letters ( IF 5.2 ) Pub Date : 2021-09-02 , DOI: 10.1021/acs.orglett.1c02532
Tianyuan Zhang 1 , Suhua Zheng 1 , Taro Kobayashi 1 , Hirofumi Maekawa 1
Affiliation  

A practical protocol for the regioselective preparation of 3-phenylpropargylsilanes and 3-phenylallylsilanes in yields of 36–77 and 48–86%, respectively, from readily accessible 3-phenylpropargyl and 1-phenylallyl pivalates was developed through reductive C(sp3)–O bond cleavage. This method represents the first example of the direct application of vastly abundant calcium granules to a reductive coupling reaction. A broad range of propargylsilanes and allylsilanes are simply prepared using easy-to-handle pivalates and chlorotrimethylsilane under mild catalyst-free and additive-free conditions.

中文翻译:

通过 Ca 促进的还原性 C(sp3)-O 键裂解对炔丙基和新戊酸烯丙酯进行区域选择性甲硅烷基化

通过还原 C(sp 3 )–开发了一种从易于获得的 3-苯基炔丙基和 1-苯基烯丙基新戊酸酯区域选择性制备 3-苯基炔丙基硅烷和 3-苯基烯丙基硅烷的实用方案,产率分别为 36-77% 和 48-86%。O 键断裂。这种方法代表了将大量钙颗粒直接应用于还原偶联反应的第一个例子。在温和的无催化剂和无添加剂的条件下,使用易于处理的新戊酸酯和氯三甲基硅烷可以简单地制备各种炔丙基硅烷和烯丙基硅烷。
更新日期:2021-09-17
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