Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 53, Issue 37, Pages 9817-9821Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201404946
Keywords
carbenoids; carbocations; carbophilicity; diazo compounds; gold
Categories
Funding
- NSF [CAREER-CHE-0844602, CHE-1228336]
- NSFC [21228204]
- National Science Foundation of China [21372266, 51302327]
- Direct For Mathematical & Physical Scien [0844602] Funding Source: National Science Foundation
- Division Of Chemistry [0844602] Funding Source: National Science Foundation
- Division Of Chemistry
- Direct For Mathematical & Physical Scien [1228336] Funding Source: National Science Foundation
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The chemoselective addition of arenes and 1,3-diketones to -aryldiazoesters was achieved through ligand-controlled gold catalysis. Unlike a dirhodium catalyst (which promotes Csp3H insertion and cyclopropanation) and a copper catalyst (which catalyzes OH and NH insertions), the gold catalyst with an electron-deficient phosphite as the ancillary ligand exclusively gave the carbophilic addition product, thus representing a new and efficient approach to form carbophilic carbocations, which selectively react with carbon nucleophiles.
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