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Beilstein J. Org. Chem. 2021, 17, 2520–2542, doi:10.3762/bjoc.17.169
Graphical Abstract
Scheme 1: Photoredox catalysis mechanism of [Ru(bpy)3]2+.
Scheme 2: Photoredox catalysis mechanism of CuI.
Scheme 3: Ligands and CuI complexes.
Scheme 4: Mechanism of CuI-based photocatalysis.
Scheme 5: Mechanisms of CuI–substrate complexes.
Scheme 6: Mechanism of CuII-base photocatalysis.
Scheme 7: Olefinic C–H functionalization and allylic alkylation.
Scheme 8: Cross-coupling of unactivated alkenes and CF3SO2Cl.
Scheme 9: Chlorosulfonylation/cyanofluoroalkylation of alkenes.
Scheme 10: Hydroamination of alkenes.
Scheme 11: Cross-coupling reaction of alkenes, alkyl halides with nucleophiles.
Scheme 12: Cross-coupling of alkenes with oxime esters.
Scheme 13: Oxo-azidation of vinyl arenes.
Scheme 14: Azidation/difunctionalization of vinyl arenes.
Scheme 15: Photoinitiated copper-catalyzed Sonogashira reaction.
Scheme 16: Alkyne functionalization reactions.
Scheme 17: Alkynylation of dihydroquinoxalin-2-ones with terminal alkynes.
Scheme 18: Decarboxylative alkynylation of redox-active esters.
Scheme 19: Aerobic oxidative C(sp)–S coupling reaction.
Scheme 20: Copper-catalyzed alkylation of carbazoles with alkyl halides.
Scheme 21: C–N coupling of organic halides with amides and aliphatic amines.
Scheme 22: Copper-catalyzed C–X (N, S, O) bond formation reactions.
Scheme 23: Arylation of C(sp2)–H bonds of azoles.
Scheme 24: C–C cross-coupling of aryl halides and heteroarenes.
Scheme 25: Benzylic or α-amino C–H functionalization.
Scheme 26: α-Amino C–H functionalization of aromatic amines.
Scheme 27: C–H functionalization of aromatic amines.
Scheme 28: α-Amino-C–H and alkyl C–H functionalization reactions.
Scheme 29: Other copper-photocatalyzed reactions.
Scheme 30: Cross-coupling of oxime esters with phenols or amines.
Scheme 31: Alkylation of heteroarene N-oxides.
Beilstein J. Org. Chem. 2020, 16, 3086–3092, doi:10.3762/bjoc.16.258
Scheme 1: Metal-catalyzed difunctionalization of unsaturated carbon–carbon bonds.
Scheme 2: Substrate scope for the synthesis of the β-fluorovinylphosphonates 2 using diethyl phosphite. React...
Scheme 3: Substrate scope for the synthesis of the β-fluorovinylphosphonates 3 using dimethyl phosphite. Reac...
Scheme 4: Radical-trapping experiments.
Scheme 5: Proposed mechanism for the silver-catalyzed phosphonofluorination of alkynes.
Scheme 6: Attempted use of a suspected phosphonofluorination intermediate to synthesize a β-fluorovinylphosph...