The Palladium-Catalyzed Trifluoromethylation of Aryl Chlorides
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Buchwald_The Palladium.pdf
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Author(s)
Cho, Eun Jin
Senecal, Todd D.
Kinzel, Tom
Zhang, Yong
Watson, Donald A.
Buchwald, Stephen Leffler
Date Issued
June 2010
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
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.
MIT Department
MIT Materials Research Laboratory
Massachusetts Institute of Technology. Department of Chemistry
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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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DOI of Published Version
https://doi.org/10.1126/science.1190524
