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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