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Highly Selective Synergistic Copper(I/II)‐Catalyzed A 3 Cross Coupling/Decarboxylative A 3 Domino Reactions in Water
Author(s) -
Feng Huangdi,
Zhao Panfeng,
Huang Liliang,
Sun Zhihua,
Tong Minchao
Publication year - 2017
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201600524
Subject(s) - chemistry , chemoselectivity , catalysis , copper , domino , aldehyde , coupling reaction , amine gas treating , cascade reaction , decarboxylation , formaldehyde , functional group , organic chemistry , combinatorial chemistry , polymer
A microwave‐assisted copper‐catalyzed A 3 cross‐coupling/decarboxylative A 3 domino reaction of a propiolic acid, an aldehyde, a formaldehyde solution and an amine is described. This strategy represents the first one‐pot cross‐coupling reaction for the direct synthesis of trisubstituted unsymmetrical 2‐butynes with a broad functional group tolerance in good yields (up to 91 %) and excellent chemoselectivity. The simultaneous activation of both the C−COOH and C−H bond of propiolic acid is crucial in this approach, and only carbon dioxide and water are generated as byproducts.