Triply Selective & Sequential Diversification at Csp3: Expansion of Alkyl Germane Reactivity for C−C & C−Heteroatom Bond Formation

We report the triply selective and sequential diversification of a single C_sp ³ carbon carrying Cl, Bpin and GeEt₃ for the straightforward construction of sp³-rich molecules. The repertoire of alkyl germane functionalizations was also significantly expanded herein.

Abstract

We report the triply selective and sequential diversification of a single C_sp ³ carbon carrying Cl, Bpin and GeEt₃ for the modular and programmable construction of sp³-rich molecules. Various functionalizations of C_sp ³−Cl and C_sp ³−BPin (e.g. alkylation, arylation, homologation, amination, hydroxylation) were tolerated by the C_sp ³−GeEt₃ group. Moreover, the methodological repertoire of alkyl germane functionalization was significantly expanded beyond the hitherto known Giese addition and arylation to alkynylation, alkenylation, cyanation, halogenation, azidation, C−S bond formation as well as the first demonstration of stereo-selective functionalization of a C_sp ³-[Ge] bond.

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