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COMMUNICATION
DOI: 10.1039/C4CC08604J
did not affect electrophile-sensitive functionalities such as
styrene (3j) and diene (3k). However, the presence of
competing nucleophiles such as three hydroxyl groups of the
cholic acid (entry 3l) and low solubility of cholic acid in
toluene resulted in a reduced yield. The acetylated cholic acid;
however, could be esterified in an excellent yield (entry 3m).
6
7
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Conclusions
In conclusion, HBDs may act as synergistic co-catalysts of
the Cu(II)-catalyzed arylation of potassium carboxylates with
diaryliodonium salts. Thiophosphoramides were found to be
significantly better HBDs than conventionally used thioureas or
squaramides in their ability to accelerate the reactions. The
preliminary data suggests that the HBD activation is
accomplished by the counterion activation of the organocopper
intermediate; however, further studies are required to clarify the
precise origins of activation. This new catalytic variant of this
transformation can be used for the arylation of various
carboxylic acids including the substrates possessing
electrophile-sensitive functionalities. We envision that these
findings can be extended to the other reactions of nucleophiles
with diaryliodonium salts.
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Acknowledgement
This work was supported by the ACS Petroleum Research Fund
(grant #53428-DNI1) and National Science Foundation
CAREER Award (CHE-1350060).
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Notes and references
Department of Chemistry, University of Michigan, Ann Arbor, MI
a
48109-1055, nagorny@umich.edu
Electronic Supplementary Information (ESI) available: [details of any
supplementary information available should be included here]. See
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