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The Palladium-Catalyzed Trifluoromethylation of Aryl Chlorides

Author(s)
Cho, Eun Jin; Senecal, Todd D.; Kinzel, Tom; Zhang, Yong; Watson, Donald A.; Buchwald, Stephen Leffler; ... Show more Show less
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Article is made available in accordance with the publisher's policy and may be subject to US copyright law. Please refer to the publisher's site for terms of use.

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Article is made available in accordance with the publisher's policy and may be subject to US copyright law. Please refer to the publisher's site for terms of use.
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Abstract
The trifluoromethyl group can dramatically influence the properties of organic molecules, thereby increasing their applicability as pharmaceuticals, agrochemicals, or building blocks for organic materials. Despite the importance of this substituent, no general method exists for its installment onto functionalized aromatic substrates. Current methods either require the use of harsh reaction conditions or suffer from a limited substrate scope. Here we report the palladium-catalyzed trifluoromethylation of aryl chlorides under mild conditions, allowing the transformation of a wide range of substrates, including heterocycles, in excellent yields. The process tolerates functional groups such as esters, amides, ethers, acetals, nitriles, and tertiary amines and, therefore, should be applicable to late-stage modifications of advanced intermediates. We have also prepared all the putative intermediates in the catalytic cycle and demonstrated their viability in the process.
Description
available in PMC 2011 June 25.
Date issued
2010-06
URI
http://hdl.handle.net/1721.1/79819
Department
Massachusetts Institute of Technology. Center for Materials Science and Engineering; Massachusetts Institute of Technology. Department of Chemistry
Journal
Science
Publisher
American Association for the Advancement of Science
Citation
Cho, E. J., T. D. Senecal, T. Kinzel, et al. 2010The Palladium-Catalyzed Trifluoromethylation of Aryl Chlorides. Science 328(5986): 1679–1681.
Version: Author's final manuscript
ISSN
0036-8075
1095-9203

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