Different methodologies for benzylic silylation reactions

June 14, 2024

• Title:       

  Different methodologies for benzylic silylation  reactions

• Image Source:

  Palladium-catalyzed silylation reaction between benzylic halides and silylboronate

• Mark:

  Scheme 1

• Associated context:

  Traditionally, the most popular synthetic route to access this kind of product is reacting the  Grignard reagents with silyl halides (Scheme 1, (a)). However, substrates with functional groups such as carbonyls, cyano, and other strong electronꢀwithdrawing groups could not be tolerated which greatly restricts its wide application in organic synthesis. Another strategy to synthesize these products was conducted by using palladium catalysts and disilanes (Scheme 1, (b)). However, only limited substrates have been examined at high temperatures. Recently, a few examples of benzylic C-H bond silylation reactions with the help of directing groups have also  40 has been elegantly developed (Scheme 1, (c)). Noticeably, He and co-workers reported the first Pd-catalyzed silylation reaction between aryl pivalates and silylboronate. In continuation of our interest in the development of C-Si bond formation, herein we would like to report a palladium-catalyzed benzylic silylation reaction using easily available benzylic halides and silyboranate as starting materials.