A New Combined Source of "CN" from N,N-Dimethylformamide and Ammonia in the Palladium-Catalyzed Cyanation of Aryl C-H Bonds

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An unprecedented protocol for cyanation at arene C-H bonds has been developed by employing N,N-dimethylformamide and ammonia as a combined source for the cyano "CN" unit. Isotopic incorporation experiments revealed that the carbon and nitrogen of the "CN" originate from the N,N-dimethyl moiety of DMF and ammonia, respectively. The present cyanation reaction shows an excellent degree of regioselectivity, producing only monosubstituted nitriles at the less hindered C-H position, and it allows for the preparation of doubly labeled nitrile compounds for the first time.
Publisher
AMER CHEMICAL SOC
Issue Date
2010-08
Language
English
Article Type
Article
Keywords

TRANSITION-METAL; HALIDES; FUNCTIONALIZATION; EFFICIENT; HALOGEN; AMINES

Citation

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, v.132, no.30, pp.10272 - 10274

ISSN
0002-7863
DOI
10.1021/ja104917t
URI
http://hdl.handle.net/10203/93433
Appears in Collection
CH-Journal Papers(저널논문)
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