Recent Progresses in Visible-Light-Driven Alkene Synthesis

doi:10.6023/cjoc202208044

Abstract

Alkenes and their functionalized derivatives represent a versatile class of building blocks in organic synthesis. The traditional synthetic methods include Wittig oleﬁnation, Peterson oleﬁnation, Horner-Wadsworth-Emmons reaction and others, and many of these classic reactions have also become textbook knowledge. Most of these methods are based on ionic pathways and some still require pre-functionalization at the sites where C—C double bonds are formed, resulting some limitations on substrate scope or functional group tolerance. Over the past few years, photoredox catalysis has become a powerful platform for new reaction design owing to its green chemistry characteristics and unique activation modes. The recently developed and representative methods for the synthesis of alkenes under photochemical conditions are summarized. Moreover, the prospects of further developments are also discussed.

Key words: visible light, photoredox catalysis, radical reaction, alkene synthesis

Cite this article

Pan-Pan Gao, Wen-Jing Xiao, Jia-Rong Chen. Recent Progresses in Visible-Light-Driven Alkene Synthesis[J]. Chinese Journal of Organic Chemistry, 2022, 42(12): 3923-3943.

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Fig. & Tab. 57

Scheme 1. General strategies to access alkenes (a) Traditional methods to construct alkenes; (b) photoredox catalytic synthesis of alkenes

Scheme 2. Decarboxylative cross-coupling of carboxylic acids with vinyl halides

Scheme 3. Mechanism for decarboxylative olefination of carboxylic acids with vinyl halides

Scheme 4. Plausible mechanism for the radical addition between vinyl sulfones and tertiary amines

Scheme 5. Photo-induced decarboxylative Heck-type coupling reaction of aliphatic acids and terminal alkenes

Scheme 6. Decarboxylative Heck reaction of (hetero)arylalkenes with aliphatic N-(acyloxy)phthalimides

Scheme 7. Photo-induced cross coupling reactions of carboxylic acids with β-aryl-vinyl halides

Scheme 8. Photo-induced alkenylation of aryl carboxylic acids and alkenyl triflates

Scheme 9. Photo-induced coupling reaction of borates with alkenyl carboxylic acids

Scheme 10. Photoredox/copper catalyzed decarboxylation difluoroacetylation of α,β-unsaturated carboxylic acids

Scheme 11. Photo-induced coupling reaction of arylalkenes with halogenated hydrocarbons

Scheme 12. Photo-induced cross-coupling of alkenyl halides with 4-alkyl-1,4-dihydropyridines

Scheme 13. Photo-induced coupling reaction of triphenylpyridinium salts with vinyl sulfones

Scheme 14. Photocatalytic coupling of alkyl bromides and alkenyl sulfones

Scheme 15. Photocatalytic coupling reaction of alkyl boronic acids with arylalkenyl sulfones

Scheme 16. Photo-induced coupling reaction of benzyl sulfonium salts with aryl alkenes

Scheme 17. Photo-induced vinylation of tetrahydrofuran with alkynes

Scheme 18. Photo-induced hydroalkylation of terminal aryl alkynes with alkyl diacyl peroxides

Scheme 19. Photo-induced cross-coupling reaction of propargyl alcohols and diazonium salts

Scheme 20. Photo-induced nickel-catalyzed hydroalkylation of internal alkynes with ether and amide α-hetero C(sp3)—H bonds

Scheme 21. Photocatalytic coupling reaction of alkynes with aryl sulfonic acids

Scheme 22. Alkylarylation of terminal alkynes by dual photoredox and nickel catalysis

Scheme 23. Photoredox catalysis ring-opening-vinylation of oxime and terminal alkynes

Scheme 24. Photoinduced deaminative coupling of alkylpyridium salts with terminal arylalkynes

Scheme 25. Photo-induced cross-coupling with N-aryltetrahydroisoquinolines and allyl derivatives

Scheme 26. Decarboxylative alylation of α-amino and phenylacetic allyl esters via dual catalysis

Scheme 27. Decarboxylative allylations of α-amino acids by dual photoredox/palladium catalysis

Scheme 28. Photo-induced coupling reactions of high-valent biquinol-silicon compounds as alkyl radical precursors

Scheme 29. Photocatalytic allyl alkylation of 4-alkyl-1,4-dihydropyridines and allyl esters

Scheme 30. Allylation of aldehydes by dual photoredox and nickel catalysis

Scheme 31. Cobalt-catalyzed allylic alkylation enabled by organophotoredox catalysis

Scheme 32. Proposed mechanism for the allylic alkylation with cobalt and photoredox catalysis.

Scheme 33. Regioselective deaminative allylation of aliphatic amines via dual cobalt and organophotoredox catalysis

Scheme 34. Photocatalytic dehydrogenative decarboxyolefination of carboxylic acids

Scheme 35. Proposed mechanism for photocatalytic dehydrogenative decarboxyolefination of carboxylic acids

Scheme 36. Dual photoredox/cobalt dual catalyzed decarboxylative elimination of N-acyl amino acids

Scheme 37. Decarboxylative ole?nation of activated aliphatic acids enabled by dual organophotoredox/copper catalysis

Scheme 38. Proposed mechanism for decarboxylative ole?nation of activated aliphatic acids

Scheme 39. Dehydrodecarboxylation ole?nation of carboxylic acids by dual photoredox/enzyme catalysis

Scheme 40. Decarboxyalkenylation of cyclic tertiary carboxylic acids by dual photoredox/iron catalysis

Scheme 41. Visible light-catalyzed dehydroolefination of naphthenes

Scheme 42. Visible light-induced α-aminoalkyl radicals and cobalt-catalyzed halogen transfer to synthesize alkenes

Scheme 43. Proposed mechanism for E2 elimination via XAT and dual photoredox-cobalt catalysis

Scheme 44. Site-selective dehydrogenation of aliphatics enabled by organophotoredox/cobalt dual catalysis

Scheme 45. Proposed mechanism for dehydrogenation of aliphatics enabled by organophotoredox/cobalt dual catalysis

Scheme 46. Photoinduced Pd-catalyzed silyl ethers into silyl enol ethers

Scheme 47. Photoinduced Pd-catalyzed C—H functionalization of aliphatic alcohols

Scheme 48. Photoinduced Pd-catalyzed for desaturation of aliphatic amines for alkene synthesis

Scheme 49. Photoinduced dehydroalkenylation of amide derivatives

Scheme 50. Photoinduced cobalt-catalyzed chemoselective dehydrogenation

Scheme 51. Photoredox/cobaloxime dual catalyzed and acceptorless dehydrogenation for the construction of alkenes

Scheme 52. Visible-light-promoted cross-coupling of aryldiazoacetates and diazocarbonyls

Scheme 53. Deoxygenative reductive olefination of aromatic aldehydes via photoredox catalysis

Scheme 54. Branch-selective alkenylation of pyridines via photoredox catalysis

Scheme 55. Visible light-promoted coupling of aryldiazoacetates to sulfur ylides

Scheme 56. Alkene synthesis by visible-light-driven photo- Wolff-Kischner reaction of sulfur ylides and N-tosylhydrazones

Scheme 57. Electro-mediated photoredox catalysis for selective C(sp3)—O cleavages of phosphinated alcohols for alkene synthesis

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