ABSTRACT
An organophotoelectrocatalytic method for the C(sp2)-H alkylation of heteroarenes with unactivated C(sp3)-H compounds through dehydrogenation cross-coupling has been developed. The C(sp2)-H alkylation combines organic catalysis, photochemistry and electrochemistry, avoiding the need for external metal-reagents, HAT-reagents, and oxidants. This protocol exhibits good substrate tolerance and functional group compatibility, providing a straightforward and powerful pathway to access a variety of alkylated heteroarenes under green conditions.
ABSTRACT
Organoelectrophotocatalytic generation of acyl radicals from formamides and aldehydes to synthesize acylated 3-CF3-2-oxindoles has been developed. This protocol features a monocatalytic system using 9,10-phenanthrenequinone (PQ) both as a catalyst and as a hydrogen atom transfer (HAT) reagent, which avoids the use of an external HAT reagent, metal reagent, and oxidant. A variety of acylated 3-CF3-2-oxindoles have been obtained in satisfactory yields from CF3-substituted N-arylacrylamides via a tandem radical cyclization.
ABSTRACT
An organoelectrophotocatalytic approach for the C-H silylation of heteroarenes through dehydrogenation cross-coupling with H2 evolution has been developed. The organoelectrophotocatalytic strategy is carried out under a simple and efficient monocatalytic system by employing 9,10-phenanthrenequinone both as an organocatalyst and as a hydrogen atom transfer (HAT) reagent, which avoids the need for an external HAT reagent, an oxidant, or a metal reagent. A variety of heteroarenes can be compatible in satisfactory yields with excellent regioselectivity.
