Aminoquinoline-assisted vinylic C–H arylation of unsubstituted acrylamide for the selective synthesis of Z olefins. Issue 12 (2nd March 2016)

• Record Type: Journal Article
• Authors: Cheng, Xiuzhi; Chen, Zhen; Gao, Yadong; Xue, Fengtian; Jiang, Chao
• Is Part Of: Organic & biomolecular chemistry. Volume 14:Issue 12(2016)
• Page Start: 3298
• Page End: 3306
• Publication Date: 2016-03-02
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/c6ob00164e
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : A method for Pd-catalyzed, aminoquinoline-directed arylation of vinylic C–H bonds with aryl iodides has been developed. This reaction represents a rare example of Pd-catalyzed vinylic C–H functionalization of unsubstituted acrylamide, allowing for preparation of Z -olefins. Abstract : A method for Pd-catalyzed, aminoquinoline-directed arylation of vinylic C–H bonds with aryl iodides has been developed. This reaction represents a rare example of Pd-catalyzed vinylic C–H functionalization of unsubstituted acrylamide, allowing for the highly regio- and stereoselective preparation of Z -olefins. High tolerance to functional groups is observed with good yields and excellent selectivity. It offers a complementary synthetic method to traditional pathways for Z -olefins.