Open AccessLigand-Enabled Pd(II)-Catalyzed C(sp3)–H Lactonization Using Molecular Oxygen as Oxidant
Author(s) -
Shaoqun Qian,
Ziqi Li,
Minyan Li,
Steven R. Wisniewski,
Jennifer X. Qiao,
Jeremy M. Richter,
William R. Ewing,
Martin D. Eastgate,
Jason S. Chen,
JinQuan Yu
Publication year - 2020
Publication title -
organic letters
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.94
H-Index - 239
eISSN - 1523-7060
pISSN - 1523-7052
DOI - 10.1021/acs.orglett.0c01243
Subject(s) - chemistry , catalysis , molecular oxygen , benzoic acid , oxygen , ligand (biochemistry) , palladium , oxygenation , combinatorial chemistry , medicinal chemistry , stereochemistry , organic chemistry , receptor , biochemistry , ecology , biology
Pd(II)-catalyzed C-H lactonization of o -methyl benzoic acid substrates has been achieved using molecular oxygen as the oxidant. This finding provides a rare example of C-H oxygenation through Pd(II)/Pd(0) catalysis as well as a method to construct biologically important benzolactone scaffolds. The use of a gas mixture of 5% oxygen in nitrogen demonstrated the possibility for its application in pharmaceutical manufacturing.