Journal
ORGANIC LETTERS
Volume 16, Issue 19, Pages 5080-5083Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol5024344
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Funding
- Indiana University
- American Chemical Society Petroleum Research Fund [PRF 52233-DNI1]
- NSF-CAREER Award [CHE-1254783]
- Eli Lilly
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The iron-catalyzed coupling of aryl sulfamates and tosylates with aryl Grignard reagents is reported for the first time. The methodology employs air-stable, low-cost FeF3 center dot 3H(2)O and the N-heterocyclic carbene ligand IPr center dot HCl as the preligand to form a long-lived catalyst upon treatment with aryl Grignards. The reaction provides a range of cross-coupled products in good-to-excellent yields. In contrast to previous reports with aryl chlorides, these reactions proceed with low levels of Grignard homocoupling regardless of the iron source.
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