A new combined source of "CN" from N,N-dimethylformamide and ammonia in the palladium-catalyzed cyanation of aryl C-H bonds

Jinho Kim; Sukbok Chang

doi:10.1021/ja104917t

A new combined source of "CN" from N,N-dimethylformamide and ammonia in the palladium-catalyzed cyanation of aryl C-H bonds

J Am Chem Soc. 2010 Aug 4;132(30):10272-4. doi: 10.1021/ja104917t.

Authors

Jinho Kim¹, Sukbok Chang

Affiliation

¹ Molecular-Level Interface Research Center and Department of Chemistry, Korea Advanced Institute of Science and Technology, Daejeon 305-701, Korea.

PMID: 20662510
DOI: 10.1021/ja104917t

Abstract

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.