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Modular Synthesis of (Borylmethyl)silanes through Orthogonal Functionalization of a Carbon Atom
Rajdip Chowdhury1, Gábor Zoltán Elek1,2, Beatriz Meana-Baamonde1,3
1Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, 10691-Stockholm, Sweden.
Abstract:
(Borylmethyl)trimethylsilanes are important building blocks in organic synthesis displaying a unique reactivity. Yet, the synthesis of more advanced derivatives is limited by the advanced silicon intermediates required for their preparation. Herein, a one-pot synthesis of (borylmethyl)silanes is developed, sourced on available alkyl-, aryl-, alkoxy-, aryloxy-, and silyl-hydrosilane materials. The privileged reactivity of N-hydroxyphthalimidyl diazoacetate (NHPI-DA) in Si-H insertion and α-silyl redox-active esters in different decarboxylative borylation reactions are scrutinized.
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