Zhang Tianyuan, Zheng Suhua, Kobayashi Taro, Maekawa Hirofumi
Department of Materials Science and Technology, Nagaoka University of Technology, 1603-1 Kamitomioka-cho, Nagaoka, Niigata 940-2188, Japan.
Org Lett. 2021 Sep 17;23(18):7129-7133. doi: 10.1021/acs.orglett.1c02532. Epub 2021 Sep 2.
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(sp)-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.
通过还原C(sp)-O键裂解，开发了一种实用的方案，可分别从易于获得的3-苯基丙炔酸叔丁酯和1-苯基烯丙基新戊酸酯以36-77%和48-86%的产率区域选择性地制备3-苯基丙炔基硅烷和3-苯基烯丙基硅烷。该方法代表了将大量丰富的钙颗粒直接应用于还原偶联反应的首个实例。在温和的无催化剂和无添加剂条件下，使用易于处理的新戊酸酯和三甲基氯硅烷可简便地制备多种丙炔基硅烷和烯丙基硅烷。
