Abstract
A direct, single synthetic homologative transformation of halostannanes into mono- or di-substituted methyl analogues is documented. Critical for the success of the operation is the excellent nucleophilicity of carbenoid-like methyllithium reagents (LiCHXY, X, Y = halogen, OR, and 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.
Highlights
A direct, single synthetic homologative transformation of halostannanes into mono- or di-substituted methyl analogues is documented
Critical for the success of the operation is the excellent nucleophilicity of carbenoid-like methyllithium reagents (LiCHXY, X, Y = halogen, OR, and CN): by individuating the reagents’ substitution pattern, the desired functionalized fragment is delivered to the electrophile
As a consequence of this significant advantage, the reactivity portfolio of these stannanes has been considerably exploited in a series of synthetic processes ranging from the equivalence with alkoxymethyl anions5 to electrophilic carbon units suitable for the preparation of multifunctionalized organotin compounds via nucleophilic substitutions
Summary
A direct, single synthetic homologative transformation of halostannanes into mono- or di-substituted methyl analogues is documented. Homologation of halostannanes with carbenoids: a convenient and straightforward one-step access to a-functionalized organotin reagents†
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