期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 61, 期 44, 页码 -出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202207472
关键词
Amidation; Carbamoyl Chloride; Cross Electrophile Coupling; Drug Diversification; Photoredox Catalysis
资金
- SERB
- India [CRG/2018/003951]
- CISR
- India [CSIR 01(3033)/21/EMR-II]
- UGC-India
- IIT Bombay
- PMRF
In this study, we have successfully constructed carbamides using the concept of cross-electrophile coupling by combining photo-redox and transition-metal catalysis. The method involves the prior formation of Ni-II-aryl halide intermediates through photoexcited Ni-halide homolysis, energy transfer from aryl bromide, and single-electron transfer from aryl chloride to generate carbamoyl radicals.
Amide bonds connect the amino acids in proteins and exist as a prevalent structural motif in biomolecules. Herein, we have exploited the concept of cross-electrophile coupling by merging the photo-redox and transition-metal catalysis to construct carbamides from superabundant (hetero)aryl halides along with commercially feasible carbamoyl chlorides. The success of this method relies on the prior formation of Ni-II-aryl halide intermediates, which involves in a photoexcited Ni-halide homolysis event by energy transfer from aryl bromide and single-electron transfer from aryl chloride to assist generation of the vital carbamoyl radical. The breadth of application of this technique is demonstrated both in inter- as well as intramolecular routes for the synthesis of a plethora of (hetero)aryl carbamides with diverse functionalities, and biologically important benzolactams.
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