Journal
ORGANIC LETTERS
Volume 19, Issue 17, Pages 4644-4647Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.7b02272
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Funding
- EPSRC [EP/M026221/1, EP/K000128/1]
- Ramsay Memorial Trust
- China Scholarship Council
- RSC Research Fund
- EPSRC [EP/K000128/1, EP/M026221/1] Funding Source: UKRI
- Engineering and Physical Sciences Research Council [EP/M026221/1, EP/K000128/1] Funding Source: researchfish
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The reaction of arynes with 1,4-dihydropyridines affords 2-aryl-1,2-dihydropyridines or 2-methylene-3-aryl-1,2,3,4-tetrahydropyridines via a regioselective C-2 or C-3 arylation. These compounds are the first series of isolable and bench-stable covalent ene adducts formed between dihydropyridines and unsaturated substrates. Experimental studies and DFT calculations provide mechanistic support for a concerted intermolecular aryne ene process, which may have implications for NAD(P)H model reactions.
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