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Chapter 69,099

Ni-Catalyzed Redox-Neutral Ring-Opening/Radical Addition/Ring-Closing Cascade of Cycloketone Oxime Esters and Vinyl Azides

Tang, Y.-Q.; Yang, J.-C.; Wang, L.; Fan, M.; Guo, L.-N.

Organic Letters 21(13): 5178-5182

2019

ISSN/ISBN: 1523-7052
PMID: 31247761
DOI: 10.1021/acs.orglett.9b01773
Accession: 069098242
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A nickel-catalyzed iminyl radical-triggered C-C bond cleavage/radical addition/cyclization cascade of oxime esters and vinyl azides is described. This protocol enables rapid access to the cyanoalkylated 3,4-dihydro-2 H-pyrroles and phenanthridines in good yields via adjustment of the substrate's properties. Moreover, these reactions proceed under mild and redox-neutral conditions with a board substrate scope and excellent functional group tolerance.

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