Carbozincation of Substituted 2-Alkynylamines, 1-Alkynylphosphines, 1-Alkynylphosphine Sulfides with Et2Zn in the Presence of Catalytic System of Ti(O-iPr)4 and EtMgBr

Abstract

The EtMgBr and Ti(O-iPr)4-catalyzed ethylzincation of 1-alkynylphosphine sulfides with Et2Zn in diethyl ether followed by hydrolysis and deuterolysis affords corresponding β,β-disubstituted 1-alkenylphosphine sulfides with high yield. The EtMgBr and Ti(O-iPr)4-catalyzed reaction of 2-alkynylamines, 1-alkynylphosphines, and 1-alkenylphosphine sulfides with Et2Zn in various solvents was studied. It has been found that the reaction of 2-alkynylamines and 1-alkynylphosphines in methylene chloride, hexane, toluene, benzene, and anisole leads to the selective formation of 2-alkenylamines and 1-alkenylphosphine oxides after oxidation with H2O2.