Highly Selective Synergistic Copper(I/II)‐Catalyzed A3 Cross Coupling/Decarboxylative A3 Domino Reactions in Water. Issue 2 (16th December 2016)

• Record Type: Journal Article
• Authors: Feng, Huangdi; Zhao, Panfeng; Huang, Liliang; Sun, Zhihua; Tong, Minchao
• Is Part Of: Asian journal of organic chemistry. Volume 6:Issue 2(2017)
• Page Start: 161
• Page End: 164
• Publication Date: 2016-12-16
• Subjects: A3 coupling -- alkynes -- copper -- cross-coupling -- domino reactions; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; 547.005
• DOI: 10.1002/ajoc.201600524
• Languages: English
• ISSNs: 2193-5807

Abstract

Abstract: 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. Abstract : 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 has been reported resulting in trisubstituted unsymmetrical 2‐butynes in good yields.