Recent Advances in Visible-Light-Induced Cross Dehydrogenation Coupling Reaction under Transition Metal-Free Conditions

doi:10.6023/cjoc201905016

Abstract

The cross dehydrogenation coupling reaction realizes direct coupling of two different X-H bonds to form a new chemical bond, thus featuring excellent step and atom economy. The traditional cross dehydrogenation coupling reaction was usually catalyzed by transition metal, which had the problems of expensive catalyst and serious pollution. Visible light-induced electron transfer is also an effective way to realize direct functionalization of X-H bonds. Visible-light-induced cross dehydrogenation coupling reaction under transition metal-free conditions is widely concerned due to the advantages of cleanliness, safety as well as high step and atom economy. Classified by the type of bonding, the research progress of these reactions is reviewed, and their future outlook is also discussed.

Key words: cross dehydrogenation coupling, visible-light-induced, transition metal-free, functionalization

Cite this article

Kong Yaolei, Xu Wenxiu, Ye Feixia, Weng Jianquan. Recent Advances in Visible-Light-Induced Cross Dehydrogenation Coupling Reaction under Transition Metal-Free Conditions[J]. Chinese Journal of Organic Chemistry, 2019, 39(11): 3065-3083.

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Fig. & Tab. 20

Scheme 1. Cross dehydrogenation coupling mechanism of N-phenyltetrahydroisoquinoline and nitromethane

Scheme 2. Cross dehydrogenation coupling mechanism of N-phenyltetrahydroisoquinoline and nucleophile

Scheme 3. Cross-dehydrogenation coupling reaction of N-aryltetrahydroquinoline and nucleophiles

Scheme 4. Cross dehydrogenation coupling mechanism of N-phenyltetrahydroisoquinoline and ethyl 2-diazoacetate

Scheme 5. Visible light-induced C-H functionalization of electron-deficient aromatics and ethers

Scheme 6. Oxidative C-H olefination of tetrahydro-β-carbolines and tetrahydroisoquinolines

Scheme 7. Cross dehydrogenation coupling mechanism of N-aryltetrahydroisoquinoline and imidazo[1, 2-a]pyridine

Scheme 8. Visible light-induced oxidative cross-coupling of glycine derivatives with indoles

Scheme 9. Visible light-induced Minisci alkylation of hetero- aromatics

Scheme 10. Cross dehydrocoupling reaction of nitrogen-containing heterocycles and formamide by benzaldehyde catalysis

Scheme 11. Cross dehydrogenation coupling mechanism of benzothiazole and formamide

Scheme 12. Reaction mechanism of phenazine salt catalyzing amidation of aromatic aldehydes

Scheme 13. Visible light-induced intramolecular amination of aromatics

Scheme 14. Cross dehydrogenation coupling reaction mechanism of phenols and amines

Scheme 15. Selective C—H amination of quinolinamides and imidazopyridines

Scheme 16. Cross dehydrocyclization reaction of glycine esters with 2, 3-dihydrofuran

Scheme 17. Cross dehydrocyclization reaction of glycine esters with α-angelica lactone

Scheme 18. Coupling-cyclization reaction of dicarbonyl compounds with thioureas

Scheme 19. Synthesis of disulfides by intermolecular dehydrocoupling reaction

Scheme 20. Cross dehydrogenation coupling reaction mechanism of mercaptan and organophosphorus compounds

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