Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 364, Issue 22, Pages 3932-3940Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.202200827
Keywords
Photoredox/Ti dual catalysis; dehydroxylation of cyclobutanone oximes; gamma-cyanoalkyl radical; redox neutral; atom- and step-economies
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Funding
- National Natural Science Foundation of China [22101135, 21502096]
- Natural Science Foundation of Jiangsu Province [BK20150652]
- Fundamental Research Funds for the Central Universities [KYQN2022058, KJQN201629]
- 333 High Level Talent Project of Jiangsu Province
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In this work, a photoredox/Ti dual-catalyzed dehydroxylation of cyclobutanone oximes has been established. The reaction proceeds under mild conditions, resulting in the formation of cyanoalkyl-substituted oxoindolines through a cascade radical addition/cyclization with N-acrylamides. The reaction shows broad substrate scope, good functional group tolerance, and can be used for late-stage functionalization of complex molecules and gram-scale synthesis, highlighting its potential value in organic synthesis.
In this work, we have established a photoredox/Ti dual-catalyzed dehydroxylation of cyclobutanone oximes. The resulting gamma-cyanoalkyl radicals undergo a cascade radical addition/cyclization with N-acrylamides to afford cyanoalkyl substituted oxoindolines under mild conditions. This reaction also exhibits broad substrate scope and good functional group tolerance. Furthermore, it is applicable to late-stage functionalization of complex molecules and gram-scale synthesis, which illustrates its potential value in organic synthesis.
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