Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 133, Issue 34, Pages 13577-13586Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja2047717
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Funding
- Welch Foundation [E-1571]
- National Institute of General Medical Sciences [R01GM077635]
- Alfred P. Sloan Foundation
- Camille and Henry Dreyfus Foundation
- Norman Hackerman Advanced Research Program
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A general method for a highly regioselective copper-catalyzed cross-coupling of two aromatic compounds using iodine as an oxidant has been developed. The reactions involve an initial iodination of one arene followed by arylation of the most acidic C-H bond of the other coupling component. Cross-coupling of electron-rich arenes, electron-poor arenes, and five- and six-membered heterocycles is possible in many combinations. Typically, a 1/1.5 to 1/3 ratio of coupling components is used, in contrast to existing methodology that often employs a large excess of one of the arenes. Common functionalities such as ester, ketone, aldehyde, ether, nitrile, nitro, and amine are well-tolerated.
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