Pd(OAc)2-Catalyzed, AgOAc-Promoted Z Selective Directed β-Arylation of Acrylamide Systems and Stereoselective Construction of Z-Cinnamamide Scaffolds

Ramarao Parella; Srinivasarao Arulananda Babu

doi:10.1021/acs.joc.5b02264

Pd(OAc)2-Catalyzed, AgOAc-Promoted Z Selective Directed β-Arylation of Acrylamide Systems and Stereoselective Construction of Z-Cinnamamide Scaffolds

J Org Chem. 2015 Dec 18;80(24):12379-96. doi: 10.1021/acs.joc.5b02264. Epub 2015 Dec 8.

Authors

Ramarao Parella¹, Srinivasarao Arulananda Babu¹

Affiliation

¹ Department of Chemical Sciences, Indian Institute of Science Education and Research (IISER) Mohali , Manauli P.O., Sector 81, SAS Nagar, Mohali, Knowledge City, Punjab 140306, India.

PMID: 26618781
DOI: 10.1021/acs.joc.5b02264

Abstract

A Pd(OAc)2-catalyzed, AgOAc-promoted and bidentate ligand-directed Z selective C-H activation, followed by the β-arylation of the C(sp(2))-H bond of N-(quinolin-8-yl)acrylamide systems with aryl- and heteroaryl iodides, and a contemporary method for the construction of various Z-cinnamamides and β,β-diarylated acrylamides are reported. A plausible reaction mechanism comprising the bidentate ligand-aided, chelation-based C-H functionalization was proposed for the observed Z selective β-arylation of N-(quinolin-8-yl)acrylamide systems.

Publication types

Research Support, Non-U.S. Gov't