Photoinduced Cross-Coupling of Trifluoromethylarenes with Heteroarenes via Unactivated C(sp3)-F and C(sp2)-H
Jiyao Zhang1, Yuxiang Zhang1, Lebin Qian1
1Key Laboratory of Synthetic and Natural Functional Molecule of the Ministry of Education, College of Chemistry & Materials Science, Northwest University, Xi'an 710127, China.
Abstract:
The installation of gem-difluoromethylene groups into two adjacent aryl groups is a formidable synthetic challenge despite their attractive structural, physical, and biochemical properties. Herein, we disclose a photoredox-catalyzed selective defluoroarylation of heteroarenes through inert C(sp3)-F and C(sp2)-H selective cleavage, which provides a straightforward route to access medicinally relevant aryl-heteroaryl or heteroaryl-heteroaryl difluoromethane scaffolds. Salient features of this reaction include readily accessible starting materials, metal-free conditions, and broad substrate scope.
Related Concept Videos
Cycloaddition Reactions: MO Requirements for Photochemical Activation
Photochemical Electrocyclic Reactions: Stereochemistry
Selection Rules: Photochemical Activation
Thermal and Photochemical Electrocyclic Reactions: Overview
Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene
Regioselectivity of Electrophilic Additions-Peroxide Effect
Electrophilic 1,2- and 1,4-Addition of HX to 1,3-Butadiene


![[DPEPhosbcpCu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2FCDNSource%2Fteasers%2F59739.jpg&w=3840&q=50)