期刊
CHEMISTRYSELECT
卷 1, 期 3, 页码 601-607出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/slct.201600147
关键词
copper; N-arylation; tautomerizable heterocycle; boronic acids; oxygenated carbazoles
资金
- CSIR-New Delhi [BSC 0108]
A general and mild strategy has been developed for the selective N-arylation of tautomerizable heterocycles with a series of arylboronic acids, using CuOTf as the catalyst and 1,10-Phen as the ligand, under base free conditions at ambient atmosphere. The reaction mechanism explored by using density functional methods revealed that both kinetic and thermodynamic controls favour N-arylation. This open-flask chemistry successfully applied for N-arylation of benzo[d] oxazol-2(3H)-one and the designed N-arylated product was subsequently manipulated in synthesizing various naturally occurring oxygenated carbazole alkaloids (e.g. clausenine, clauraila A, clausenal).
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