Pd(II)-catalyzed cross-coupling of sp3 C-H Bonds with sp2 and sp3 boronic acids using air as the oxidant.
O-Methyl hydroxamic acids, readily available from carboxylic acids, are found to be extremely reactive for beta-C-H activation by Pd(OAc)2. This reactivity is exploited to develop the first example of cross-coupling sp3 C-H bonds with sp3 boronic acids. Air was shown to be a suitable stoichiometric oxidant for the catalytic oxidative coupling reaction. A biologically active natural product is readily converted to its novel analogues through this coupling reaction.
Wang
Dong-Hui
DH
Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, USA.
Wasa
Masayuki
M
Giri
Ramesh
R
Yu
Jin-Quan
JQ
D000388:Air; D001897:Boronic Acids / Q000138:chemical synthesis / Q000737:chemistry*; D002384:Catalysis; D009930:Organic Chemicals / Q000138:chemical synthesis*; D016877:Oxidants / Q000737:chemistry*; D010165:Palladium / Q000737:chemistry
D001897:Boronic Acids; D009930:Organic Chemicals; D016877:Oxidants; D010165:Palladium