Nickel/photoredox dual catalyzed arylalkylation of nonactivated alkenes

Abstract

Alkene dicarbofunctionalization is an efficient strategy and operation-economic fashion for introducing complexity in molecules. A nickel/photoredox dual catalyzed arylalkylation of nonactivated alkenes for the simultaneous construction of one C(sp3)−C(sp3) bond and one C(sp3)−C(sp2) bond has been developed. The mild catalytic method provided valuable indanethylamine derivatives with wide substrate scope and good functional group compatibility. An enantioselective dicarbofunctionalization was also achieved with pyridine-oxazoline as a ligand. The efficiency of metallaphotoredox dicarbofunctionalization was demonstrated for the concise synthesis of pharmaceutically active compounds.

Cu-catalyzed alkylarylation of alkenes via N-directed remote C(sp3)–H functionalization

“…1 Among them, the difunctionalization of alkenes as the most prevalent multicomponent reaction has attracted considerable attention because it allows the simultaneous installation of two functional groups into the CC bond. 2 In this context, the transition-metal-catalyzed three-component dicarbofunctionalization of alkenes has made great progress, featuring outstanding methods such as 1,2-alkylarylation 3 and 1,2-diarylation. 4 Among them, Xia's group achieved the arylalkylation of nonactivated alkenes using nickel/photoredox dual catalysis, leading to the efficient synthesis of indanethylamine derivatives.…”

Nickel metallaphotoredox-catalyzed C–O bond activation/Csp2–Csp3 coupling enabled by phosphine

“…The capture of the alkyl radical by the Ni( ii ) species II furnished the Ni( iii ) intermediate III , which underwent reductive elimination to deliver the desired coupling product as well as the Ni( i ) species IV . Reduction of the Ni( i ) species IV ( E red p/2 [Ni I /Ni 0 ] = −1.17 V vs. SCE in THF) 25 by Ir( ii ) ( E red 1/2 [Ir III /Ir II ] = −1.37 vs. SCE in MeCN) 21,26 regenerates the Ni(0) catalyst I and Ir( iii ), allowing the catalytic cycle to continue.…”