Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 364, Issue 8, Pages 1388-1393Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.202101519
Keywords
trifunctionalization of 5-hexenenitriles; selective cyano migration; trifluoromethyl radical; remote functionalization; photoredox catalysis
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Funding
- National Natural Science Foundation of China [21502096]
- Natural Science Foundation of Jiangsu Province [BK20150652]
- Fundamental Research Funds for the Central Universities [KJQN201629, KJQN201944, KYZ201749]
- 333 High Level Talent Project of Jiangsu Province
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In this study, a photoredox catalyzed trifluoromethyl radical-triggered trifunctionalization of 5-hexenenitriles via cyano group migration is reported. The migration of the cyano group shows high chemo-selectivity even in the presence of aryl or heteroaryl groups as competitors. This protocol provides a simple access to CF3-containing compounds with high molecular complexity and functional group diversity. The successful gram-scale reaction and the versatility of the products in derivative synthesis illustrate the potential value of this transformation in synthetic chemistry.
A photoredox catalyzed trifluoromethyl radical-triggered trifunctionalization of 5-hexenenitriles via cyano group migration is reported. The cyano group migration is of high chemo-selectivity even in the presence of aryl or heteroaryl groups as competitors. This protocol provides a facile access to a broad scope of CF3-containing compounds with high molecular complexity and functional group diversity. The success of gram-scale reaction and the versatility of products in derivative synthesis illustrate the potential value of this transformation in synthetic chemistry.
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