Abstract
Tetraorganosilane-type reagents that contain a 2-(hydroxymethyl)phenyl group are invented for silicon-based cross-coupling and carbonyl addition reactions. According to the reagent design, a proximal hydroxy group allows transmetallation of organic groups on silicon with palladium(II), copper(I or II), or rhodium(I) to participate in various transition metal-catalyzed C-C bond forming reactions under mild conditions with excellent chemoselectivity. High stability of the newly developed tetraorganosilicon reagents is demonstrated by their functionalization under various acidic, basic, and oxidative conditions with the silyl group intact. Moreover, simple control of their reactivity by orthogonal protection/deprotection allows highly efficient synthesis of functional molecules such as oligoarenes through iterative cross-coupling/deprotection sequences.
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