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Homologation of Halostannanes with Carbenoids: a Convenient and Straightforward One-step Access to α-Functionalized Organotin Reagents

Abstract

A direct, single synthetic homologative transformation of halostannanes into mono- or di-substitutedmethyl analogues is documented. Critical for the success of the operation is the excellent nucleophilicity of carbenoids-like methyllithium reagents (LiCHXY - X, Y = halogen, OR, CN): by simply individuating the reagents’ substitution pattern, the desired functionalized fragment is delivered to the electrophile. The wide scope of the protocol is evidenced also in the case of analogous halogermanium compounds. The tandem homologation-quenching with nucleophiles and the use of α-chloroallyllithium is also discussed.

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Publication details

The article was received on 14 Jun 2018, accepted on 09 Aug 2018 and first published on 09 Aug 2018


Article type: Communication
DOI: 10.1039/C8CC04786C
Citation: Chem. Commun., 2018, Accepted Manuscript
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    Homologation of Halostannanes with Carbenoids: a Convenient and Straightforward One-step Access to α-Functionalized Organotin Reagents

    S. Touqeer, L. Castoldi, T. langer, W. Holzer and V. Pace, Chem. Commun., 2018, Accepted Manuscript , DOI: 10.1039/C8CC04786C

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