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Mannich Reactions of Alkynes: Mechanistic Insights and the Role of Sub‐Stoichiometric Amounts of Alkynylcopper(I) Compounds in the Catalytic Cycle
Author(s) -
Buckley Benjamin R.,
Khan Am.,
Heaney Harry
Publication year - 2012
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201103987
Subject(s) - iminium , alkyne , catalysis , stoichiometry , chemistry , catalytic cycle , copper , component (thermodynamics) , combinatorial chemistry , organic chemistry , physics , thermodynamics
Yellow polymeric alkynylcopper(I) compounds observed in the three‐component Mannich reactions of alkynes, secondary amines and aldehydes are shown to be pre‐catalysts that give rise to catalytic copper(I) alkyne complexes by interaction with secondary amines (see scheme). Interaction of these complexes with iminium ions (formed from aldehydes or their equivalents, including CH 2 Cl 2 ), results in the formation of Mannich bases in high yields.