American Chemical Society
jo5b02264_si_002.cif (243.53 kB)

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

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posted on 2015-12-18, 00:00 authored by Ramarao Parella, Srinivasarao Arulananda Babu
A Pd­(OAc)2-catalyzed, AgOAc-promoted and bidentate ligand-directed Z selective C–H activation, followed by the β-arylation of the C­(sp2)–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.