Please use this identifier to cite or link to this item: http://hdl.handle.net/10397/23559
Title: Palladium(II)-catalyzed direct ortho-C-H acylation of anilides by oxidative cross-coupling with aldehydes using tert-butyl hydroperoxide as oxidant
Authors: Chan, CW
Zhou, Z
Yu, WY 
Keywords: 2-aminobenzophenones
acylation
C-H activation
Friedel-Crafts reaction
palladium
Issue Date: 2011
Publisher: Wiley-VCH
Source: Advanced synthesis & catalysis, 2011, v. 353, no. 16, p. 2999-3006 How to cite?
Journal: Advanced synthesis & catalysis 
Abstract: An efficient palladium-catalyzed C-H acylation with aldehydes using tert-butyl hydroperoxide (TBHP) transforms various anilides into synthetically useful 2-aminobenzophenone derivatives under mild conditions (40°C, 3 h). The acylation reaction exhibits excellent regioselectivity and functional group tolerance, and simple aromatic aldehydes, functionalized aliphatic aldehydes and heteroaromatic aldehydes are effective coupling partners. The acylation reaction is probably initiated by a rate-limiting electrophilic C-H cyclopalladation (k H/k D=3.6; ρ +=-0.74) to form an arylpalladium complex, followed by acyl radical functionalization.
URI: http://hdl.handle.net/10397/23559
ISSN: 1615-4150
EISSN: 1615-4169
DOI: 10.1002/adsc.201100472
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