Article Dans Une Revue Organic Letters Année : 2021

Radical Germylzincation of Aryl- and Alkyl-Substituted Internal Alkynes

Résumé

The stereoselective germylzincation of internal alkynes delivering trisubstituted vinylgermanes is achieved via a radical chain process involving Ph3GeH and Et2Zn with AIBN as initiator. Excellent levels of regiocontrol are observed for non-symmetric (aryl, alkyl)-substituted alkynes, as well as for propargylic alcohols with aryl-, alkyl-, or silyl-substituted alkynes. The germylzincation reaction can be combined in one pot with the Cu(I)-mediated electrophilic substitution of the C(sp 2)-Zn bond to obtain synthetically challenging tetrasubstituted vinylgermanes.

Domaines

Chimie
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Dates et versions

hal-03372809 , version 1 (11-10-2021)

Identifiants

Citer

Karen de La Vega-Hernández, Fabrice Chemla, Franck Ferreira, Olivier Jackowski, Alejandro Perez-Luna. Radical Germylzincation of Aryl- and Alkyl-Substituted Internal Alkynes. Organic Letters, 2021, 23 (11), pp.4426-4430. ⟨10.1021/acs.orglett.1c01367⟩. ⟨hal-03372809⟩
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