Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 86, Issue 14, Pages 9587-9602Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.1c00871
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Funding
- NIT Meghalaya
- DST (INSPIRE)
- SERB-DST [ECR/2017/001434]
- CSIR [01(2998)/19/EMR-II, 02(0338)/18/EMR-II]
- MHRD
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This study presents a new method for direct photochemical dehydrogenative C-N coupling, in which the reaction energy is reduced by the N-H···π interaction.
Herein, we report a direct photochemical dehydrogenative C-N coupling of unactivated C(sp(2))-H and N(sp(2))-H bonds. The catalysts or additive-free transformation of 2-[1,1'-biphenyl]-2-yl)-1H-benzo[d]imidazole to benzo[4,5]imidazo[1,2-f]phenanthiidine was achieved at, similar to 350 nm of irradiation via epsilon-hydrogen abstraction. DFT calculations helped to understand that the N-H center dot center dot center dot pi interaction was essential for the reaction to proceed at a lower energy than expected.
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