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Palladium(II)‐Catalyzed Direct ortho ‐CH Acylation of Anilides by Oxidative Cross‐Coupling with Aldehydes using tert ‐Butyl Hydroperoxide as Oxidant
Author(s) -
Chan ChunWo,
Zhou Zhongyuan,
Yu WingYiu
Publication year - 2011
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201100472
Subject(s) - chemistry , acylation , regioselectivity , electrophile , palladium , catalysis , medicinal chemistry , oxidative phosphorylation , functional group , organic chemistry , biochemistry , polymer
An efficient palladium‐catalyzed CH 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 CH cyclopalladation ( k H / k D =3.6; ρ + =−0.74) to form an arylpalladium complex, followed by acyl radical functionalization.