期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 85, 期 19, 页码 12482-12504出版社
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.0c01703
关键词
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资金
- Department of Science and Technology (DST/SERB) [EMR/2016/007042]
- CSIR [0333/NS-EMR II]
The one-pot synthetic strategies for 2,4,6-triarylnicotinonitriles and 2,5-diaryl-1H-pyrrole-3-carbonitriles have been accomplished via a Pd-catalyzed coupling of arylboronic acid with 2-(3-oxo-1,3-diarylpropyl)malononitrile and 2-(2-oxo-2-arylethyl)malononitrile, respectively, under mild reaction conditions, followed by intramolecular cyclization of an intermediate formed after the regeneration of the catalyst under acidic reaction conditions. The cascade reactions proceed in 1,2-dichloroethane solvent under visible-light irradiation, and the active catalyst is generated in situ in the presence of catalytic amounts of Pd(OAc)(2) and 2,2'-bipyridine. The active Pd catalyst undergoes photoexcitation by the virtue of metal-to-ligand charge transfer (MLCT), and subsequent redox trans-metalation occurs with arylboronic acid, thus obviating the necessity of any exogenous photosensitizer. The targeted products, composed of a new C-C, a C-N, a C=N, and two new C=C bonds, were isolated in good yields.
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