期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 131, 期 27, 页码 9488-+出版社
AMER CHEMICAL SOC
DOI: 10.1021/ja9031659
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资金
- University of Washington
- National Science Foundation
- Division Of Chemistry
- Direct For Mathematical & Physical Scien [0747543] Funding Source: National Science Foundation
This report describes a unique Pd-catalyzed oxidative carboamination of protected aminoalkenes in which inexpensive unactivated nucleophilic arenes are incorporated to give carboamination products in good yields. A variety of protected amide and carbamate groups are tolerated, and various five-, six-, and seven-membered rings are formed in good yields. Under these conditions, halobenzenes are activated at the C-H bond rather than the C-X bond, and very high regiosetectivity for the para substitution product is observed in all cases. We propose that this carboamination takes place via electrophilic aromatic substitution of a Pd(IV) alkyl intermediate.
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