ORGANIC
LETTERS
2
011
Vol. 13, No. 8
062–2064
Pd(II)-Catalyzed Decarboxylative
Cross-Coupling of Potassium
2
Aryltrifluoroborates with r-Oxocarboxylic
Acids at Room Temperature
Mingzong Li, Cong Wang, and Haibo Ge*
Department of Chemistry and Chemical Biology, Indiana University Purdue University
Indianapolis (IUPUI), Indianapolis, Indiana 46202, United States
Received February 20, 2011
ABSTRACT
A novel Pd-catalyzed decarboxylative cross-coupling of potassium aryltrifluoroborates with R-oxocarboxylic acids is performed at room
temperature. This reaction provides an efficient access to aryl ketones under mild conditions.
Transition-metal-catalyzed decarboxylative coupling has
emerged as a powerful method for C-C bond formation,
and numerous studies have been carried out in this area in
Ketones are important functional groups in medicine
and biologically active natural products. Aryl ketone
formation through Pd-catalyzed decarboxylative cross
coupling was first reported by Goossen and co-workers
using aryl halides with potassium R-oxocarboxylates in
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recent years. Aside from the well-established decarboxyla-
2
tive allylation of esters, decarboxylative cross-coupling of
carboxylic acids with activated or unactivated (hetero) arenes
4
the presence of a Cu(I) source (eq 1). Recently,
palladium(II)-catalyzed decarboxylative acylation of ar-
3
has been of recent interest, and significant progress has been
made to improve substrate scope and product diversity.
enes with R-oxocarboxylic acids was also reported from
our laboratory (eq 2). However, these processes suffer
either from high reaction temperatures (eq 1) or restricted
5
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0.1021/ol200459v r 2011 American Chemical Society
Published on Web 03/10/2011