Sarkar Writhabrata, Mishra Aniket, Bhowmik Arup, Deb Indubhusan
Organic and Medicinal Chemistry Division, CSIR-Indian Institute of Chemical Biology, 4-Raja S. C. Mullick Road, Jadavpur, Kolkata 700032, India.
Org Lett. 2021 Jun 18;23(12):4521-4526. doi: 10.1021/acs.orglett.1c01129. Epub 2021 May 13.
A copper-catalyzed method for direct intermolecular -silylation of benzamides has been developed that affords organosilane products in moderate to high yields. The key features include: (i) use of commercially available disilanes as a silicon source with 8-aminoquinoline as a bidentate directing group, (ii) use of earth-abundant first-row transition metal, (iii) operationally simple conditions without the need of an inert atmosphere, and (iv) tolerance of a wide range of functional groups. The practicality and effectiveness of this method have been demonstrated by a gram-scale experiment. This strategy, therefore, constitutes a convenient way of constructing C-Si bonds useful for synthetic organic chemistry.
已开发出一种铜催化的苯甲酰胺直接分子间硅基化方法，该方法能以中等至高产率得到有机硅烷产物。其关键特征包括：（i）使用市售的乙硅烷作为硅源，8-氨基喹啉作为双齿导向基团；（ii）使用地壳中储量丰富的第一行过渡金属；（iii）操作条件简单，无需惰性气氛；（iv）对多种官能团具有耐受性。该方法的实用性和有效性已通过克级实验得到证明。因此，该策略构成了一种构建对有机合成化学有用的C-Si键的便捷方法。
