Palladium-catalyzed silyl C(sp3)–H bond activation

Abstract

The first transition-metal-catalyzed activation of silyl C(sp³)–H bond was realized and synthetically applied. A variety of organic skeletons substituted with SiMe₃ groups could undergo the Pd-catalyzed intramolecular coupling reaction, resulting in an unprecedented synthetic method for yielding six-membered silacycles. It was found that the adjacent Si atom played an essential role for the activation of the C(sp³)–H bond of the SiMe₃ group; no activation reaction of the C(sp³)–H bond of the CMe₃ group took place under the same reaction conditions.