Pd-catalyzed ortho-C-H acylation/cross coupling of aryl ketone O-methyl oximes with aldehydes using tert-butyl hydroperoxide as oxidant.
A Pd-catalyzed protocol for direct C-H bond acylation by cross coupling of aryl ketone oximes and aldehydes using tert-butyl hydroperoxide (TBHP) as oxidant was developed. With oximes as a directing group for the C-H activation, the coupling with aldehydes was achieved with remarkable regioselectivity. The acylation reactions exhibit excellent functional group tolerance, and both aliphatic and heteroaromatic aldehydes can be effectively coupled to the oximes.
Chan
Chun-Wo
CW
State Key Laboratory of Chirosciences and the Open Laboratory of Chirotechnology of the Institute of Molecular Technology for Drug Discovery and Synthesis, Department of Applied Biology and Chemical Technology, The Hong Kong Polytechnic University, Hung Hom, Kowloon, Hong Kong.
Zhou
Zhongyuan
Z
Chan
Albert S C
AS
Yu
Wing-Yiu
WY
D000215:Acylation; D000447:Aldehydes / Q000737:chemistry*; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D007659:Ketones / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D016877:Oxidants / Q000737:chemistry*; D010091:Oximes / Q000737:chemistry*; D010165:Palladium / Q000737:chemistry*; D013237:Stereoisomerism; D020122:tert-Butylhydroperoxide / Q000737:chemistry*
D000447:Aldehydes; D007659:Ketones; D016877:Oxidants; D010091:Oximes; D010165:Palladium; D020122:tert-Butylhydroperoxide