Herein, we report a protocol for direct visible-light-mediated Minisci C–H alkylation of heteroarenes with unactivated alkyl halides using molecular oxygen as an oxidant at room temperature.
Formyl-selective deuteration of aldehydes with D2O mediated by the synergistic combination of light-driven, polyoxometalate-facilitated HAT and thiol catalysis is reported.
Ketyl radical coupling reactions for the construction of diversely functionalized alcoholsh ave been continuously developed for many decades. Based on the recently widespreada pplication of photocatalysis, ketyl radical coupling reactions have also witnessed rapid development. This Minireview aims to briefly and concisely summarize the methods to construct ketyl radical intermediates through visible-light photocatalysis over the past 10 years. The ketylradical-generation activators are grouped as Lewis acids, Brønsted acids, in situ generatedB rønsted acids, and others.Scheme3.Lithium salt activated radical-radical cross-coupling reactionso f amines and carbonyls;D MAP = 4-(dimethylamino)pyridine.Scheme4.Enantioselective reductive cross-coupling of nitrones with aldehydes;S c(OTf) 3 = scandium(III) trifluoromethanesulfonate, TEEDA = tetramethylethylenediamine,D CE = 1,2-dichloroethane.
A photoredox-mediated direct cross-dehydrogenative coupling reaction to accomplish α-aminoalkylation of N-heteroarenes is reported. This mild reaction has a broad substrate scope, offers the first general method for synthesis of aminoalkylated N-heteroarenes without the need for substrate prefunctionalization, and is scalable to the gram level. Furthermore, the reaction was found to be applicable to other hydrogen donors besides amines (i.e., ethers, an aldehyde, a formamide, p-xylene, and alkanes), thus enabling the preparation of N-heteroarenes bearing various types of substituents.
In this study, a new C(sp 3 )−H monofluoroalkenylation reaction involving cooperative visible-light photoredox catalysis and hydrogen-atomtransfer catalysis to afford products generated by selective hydrogen abstraction and radical−radical cross-coupling was described. This mild, efficient reaction shows high regioselectivity for the α-carbon atoms of amines, ethers, and thioethers and thus allows the preparation of monofluoroalkenes bearing various substituents. The reaction was applied to two bioactive molecules, indicating its utility for late-stage monofluoroalkenylation of compounds with inert C(sp 3 )−H bonds.
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