Open AccessPalladium(II)-Catalyzed Tandem Oxidative Acetoxylation/ortho C–H Activation/Carbocyclization of Arylallenes
Author(s) -
Javier Mazuela,
Debasis Banerjee,
JanE. Bäckvall
Publication year - 2015
Publication title -
journal of the american chemical society
Language(s) - Uncategorized
Resource type - Journals
SCImago Journal Rank - 7.115
H-Index - 612
eISSN - 1520-5126
pISSN - 0002-7863
DOI - 10.1021/jacs.5b06068
Subject(s) - chemistry , allene , catalysis , tandem , oxidative phosphorylation , palladium , limiting , oxidative addition , cascade reaction , combinatorial chemistry , medicinal chemistry , stereochemistry , organic chemistry , biochemistry , mechanical engineering , materials science , engineering , composite material
Herein we report an example of tandem oxidative acetoxylation/carbocyclization of arylallenes 1 using Pd(OAc)2. The catalytic protocol is highly selective and provides access to new C-C and C-O bonds leading to a carbocyclization. The reaction proceeds via C-H activation by Pd. Mechanistic investigations show that the C-H activation is not the rate-limiting step and indicate that the reaction proceeds via acetoxylation of the allene.
Accelerating Research
Robert Robinson Avenue,
Oxford Science Park, Oxford
OX4 4GP, United Kingdom
Address
John Eccles HouseRobert Robinson Avenue,
Oxford Science Park, Oxford
OX4 4GP, United Kingdom