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Pd(II)/Ag(I)-Promoted One-Pot Synthesis of Cyclic Ureas from (Hetero)Aromatic Amines and Isocyanates

Title
Pd(II)/Ag(I)-Promoted One-Pot Synthesis of Cyclic Ureas from (Hetero)Aromatic Amines and Isocyanates
Author
윤소원
Keywords
CATALYZED OXIDATIVE CYCLIZATION; C-H AMINATION; N-SUBSTITUTED 1,3-DIHYDROBENZIMIDAZOL-2-ONES; INTRAMOLECULAR CYCLIZATION; CARBOXYLIC-ACIDS; CROSS-COUPLING/CYCLIZATION; REGIOSELECTIVE SYNTHESIS; ANTISECRETORY ACTIVITY; MEDIATED REACTIONS; BENZIMIDAZOLONES
Issue Date
2016-12
Publisher
AMER CHEMICAL SOC
Citation
ORGANIC LETTERS, v. 18, NO. 23, Page. 6140-6143
Abstract
A simple and facile one-pot reaction has been developed to afford a diverse range of N,N'-disubstituted benzimidazolones and imidazopyridinones containing two differently substituted N atoms. A cooperative Pd(II)/Ag(I) system promotes the sequential addition/intramolecular C-H amidation reaction of (hetero)aromatic amines and isocyanates, leading to the formation of two C-N bonds. A mechanism involving radical intermediates generated by single-electron transfer (SET) in the presence of a Ag2CO3 oxidant and Pd(OAc)(2) Lewis acid is proposed. This protocol offers an operationally easy, simple, and robust approach with the use of readily available starting materials, good functional group tolerance, and high efficiency.
URI
https://pubs.acs.org/doi/10.1021/acs.orglett.6b03151http://repository.hanyang.ac.kr/handle/20.500.11754/102319
ISSN
1523-7060; 1523-7052
DOI
10.1021/acs.orglett.6b03151
Appears in Collections:
COLLEGE OF NATURAL SCIENCES[S](자연과학대학) > CHEMISTRY(화학과) > Articles
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