Triply Selective & Sequential Diversification at C sp 3 : Expansion of Alkyl Germane Reactivity for C-C & C-Heteroatom Bond Formation.

Authors :: Ahrweiler E
Schoetz MD
Singh G
Bindschaedler QP
Sorroche A
Schoenebeck F
Source :: Angewandte Chemie (International ed. in English) [Angew Chem Int Ed Engl] 2024 Apr 15; Vol. 63 (16), pp. e202401545. Date of Electronic Publication: 2024 Mar 08.
Publication Year :: 2024
Abstract: We report the triply selective and sequential diversification of a single C <subscript>sp</subscript> <superscript>3</superscript> carbon carrying Cl, Bpin and GeEt <subscript>3</subscript> for the modular and programmable construction of sp <superscript>3</superscript> -rich molecules. Various functionalizations of C <subscript>sp</subscript> <superscript>3</superscript> -Cl and C <subscript>sp</subscript> <superscript>3</superscript> -BPin (e.g. alkylation, arylation, homologation, amination, hydroxylation) were tolerated by the C <subscript>sp</subscript> <superscript>3</superscript> -GeEt <subscript>3</subscript> 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 <subscript>sp</subscript> <superscript>3</superscript> -[Ge] bond.<br /> (© 2024 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH.)

Full Text Access

Tools