Journal
ACS CATALYSIS
Volume 10, Issue 1, Pages 154-159Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acscatal.9b04411
Keywords
Minisci reaction; photoredox; nitrogen-heteroarenes; aldehydes; alkylation; benzylation
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Funding
- National Natural Science Foundation of China [21502161, 21602187]
- Collaborative Innovation Center of New Chemical Technologies for Environmental Benignity and Efficient Resource Utilization
- Science and Technology Planning Project of Hunan Province [2019RS2039]
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Radical addition is a robust tool for bond formation. While ketyl radical reactivity of aldehydes by photoredox has been well-established, herein, we have now revealed a pathway for umpolung addition of aldehydes with or without external reductant. Hence, the reductive alkylations and challenging benzylations of nitrogen heteroarenes (i.e., Minisci reactions) are enabled by the bromide-promoted visible light-mediated photocatalysis. The present protocol offers a mild, viable method for late-stage alkylations and transition-metal-free benzylations of biologically active nitrogen-heteroarene molecules. Mechanistic studies are indicative of a bromide-initiated acyl radical mechanism in the absence of external reductant.
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