4.7 Article

Photoredox Catalyzed Trifluoromethyl Radical-Triggered Trifunctionalization of 5-Hexenenitriles via Cyano Migration

Journal

ADVANCED SYNTHESIS & CATALYSIS
Volume 364, Issue 8, Pages 1388-1393

Publisher

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

Funding

  1. National Natural Science Foundation of China [21502096]
  2. Natural Science Foundation of Jiangsu Province [BK20150652]
  3. Fundamental Research Funds for the Central Universities [KJQN201629, KJQN201944, KYZ201749]
  4. 333 High Level Talent Project of Jiangsu Province

Ask authors/readers for more resources

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.

Authors

I am an author on this paper
Click your name to claim this paper and add it to your profile.

Reviews

Primary Rating

4.7
Not enough ratings

Secondary Ratings

Novelty
-
Significance
-
Scientific rigor
-
Rate this paper

Recommended

No Data Available
No Data Available