Z∶E Selective Preparation of Disubstituted Internal Alkenes and Trisubstituted Alkenes

doi:10.6023/cjoc202212039

Abstract

Olefin is one of the most important bulk chemicals in industry as well as commonly used starting materials in pharmaceutical field. Since Z-olefins and E-olefins exhibit great differences in physicochemical properties and biological activities, the Z∶E configuration control has been playing important roles in olefin preparation. The selective synthetic methods of Z∶E configurations of disubstituted inner alkenes and trisubstituted alkenes are reviewed, including the Wittig reaction, substituted alkane elimination reaction, olefin isomerization reaction, olefin metathesis, olefin coupling reaction, and alkyne addition reaction. The catalyst types and controlling factors of Z∶E selectivity in these synthetic examples are described in detail.

Key words: disubstituted internal olefins, trisubstituted olefins, Z∶E selectivity

Cite this article

Ping Guo, Yong Zhou, Jie Zhao. Z∶E Selective Preparation of Disubstituted Internal Alkenes and Trisubstituted Alkenes[J]. Chinese Journal of Organic Chemistry, 2023, 43(3): 855-872.

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Fig. & Tab. 64

Scheme 1. Ruthenium-catalyzed cross-olefination of diazo compounds with sulfoxonium ylides Reproduced from Ref. [31] with permission from John Wiley and Sons

Scheme 2. Reaction and possible mechanism of selective formation of Z-α,β-unsaturated esters by α-alkyl diazo esters catalyzed by TrBF4 Reproduced from Ref. [32] with permission from the Royal Society of Chemistry

Scheme 3. Photocatalytic configuration transformation of olefin Reproduced from Ref. [33] with permission from the Royal Society of Chemistry

Scheme 4. Immobilization of the photoredox catalyst in ionic liquid for the photoredox isomerization of stilbene Reproduced from Ref. [34] with permission from John Wiley and Sons

Scheme 5. Ru complex catalyzed high Z-selectivity and enantioselectivity ring-open/cross metathesis reaction Reproduced from Ref. [37] with permission from the American Chemical Society

Scheme 6. Mo compound catalyzed olefin metathesis reactions to obtain trifluoromethyl-substituted olefin Reproduced from Ref. [39] with permission from Springer Nature

Scheme 7. Selective semi-hydrogenation of alkynes catalyzed by ruthenium Reproduced from Ref. [40] with permission from the American Chemical Society

Scheme 8. Mechanism of semi-hydrogenation of alkynes catalyzed by an unsupported nanoporous palladium catalyst Reproduced from Ref. [41] with permission from the American Chemical Society

Scheme 9. Preparation of cis-alkenes by selective semi-hydro- genation of heterogeneous palladium-catalyzed alkynes Reproduced from Ref. [42] with permission from the American Chemical Society

Scheme 10. Palladium-catalyzed ligand regulating selective hydrogenation of alkynes Reproduced from Ref. [43] with permission from John Wiley and Sons

Scheme 11. Palladium-catalyzed alkyne reduction coupling reaction Reproduced from Ref. [44] with permission from John Wiley and Sons

Scheme 12. Nickel catalyzed selective semi-hydrogenation of alkynes Reproduced from Ref. [45] with permission from John Wiley and Sons

Scheme 13. Copper catalyzed selective hydroalkylation of alkynes Reproduced from Ref. [46] with permission from the American Chemical Society

Scheme 14. Possible mechanism of hydrogenalkylation of alkynes catalyzed by silver Reproduced from Ref. [48] with permission from the American Chemical Society

Scheme 15. Preparation of olefin by direct decarboxylation of phenylacetic acid Reproduced from Ref. [49] with permission from the American Chemical Society

Scheme 16. Fe-catalyzed α-olefination of methyl-substituted N-heteroarenes with primary alcohols Reproduced from Ref. [51] with permission from the American Chemical Society

Scheme 17. Decarbonylation strategies for electron donor-acce- ptor reactions Reproduced from Ref. [52] with permission from the Royal Society of Chemistry

Scheme 18. Nickel-catalyzed stereoselective alkenylation of ketones mediated by hydrazine Reproduced from Ref. [53] with permission from the American Chemical Society

Scheme 19. Cobalt-catalyzed Z to E isomerization of β-substi- tuted styrenes Reproduced from Ref. [54] with permission from the American Chemical Society

Scheme 20. Iridium catalyzed monoisomerization of 1-alkenes to trans-2-alkenes Reproduced from Ref. [55] with permission from John Wiley and Sons

Scheme 21. Visible-light-cobalt catalyzed selective isomerization of olefin Reproduced from Ref. [56] with permission from John Wiley and Sons

Scheme 22. (Ni)(I)-catalyzed intramolecular 1,3-hydrogen atom relocation Reproduced from Ref. [57] with permission from the American Association for the Advancement of Science

Scheme 23. Mn(I) pincer complexes catalyzed olefin transposition via N—H cooperativity Reproduced from Ref. [58] with permission from the American Chemical Society

Scheme 24. Cross-coupling of aldehydes facilitated by phosphonyl phosphonate esters Reproduced from Ref. [59] with permission from the American Chemical Society

Scheme 25. Manganese catalyzed dehydrogenation of alcohol to hydrazine/hydrazone directly to alkenes Reproduced from Ref. [60] with permission from John Wiley and Sons

Scheme 26. Direct dehydrogenative alkyl Heck-couplings of aryl alkenes with aldehydes catalyzed by nickel Reproduced from Ref. [61] with permission from Springer Nature

Scheme 27. Oxidative Heck reactions and ligands structure of POP-9 Reproduced from Ref. [62] with permission from John Wiley and Sons

Scheme 28. 2-Bromophenol catalyzed Heck coupling reaction of alkenes with fluoroalkyl iodide Reproduced from Ref. [63] with permission from the Royal Society of Chemistry

Scheme 29. Rhodium-catalyzed deoxidation and boration of ketone with B2pin2 Reproduced from Ref. [64] with permission from the American Chemical Society

Scheme 30. Cu(I)-catalyzed C—H alkenylation of tertiary C(sp3)—H bonds of 3?aryl benzofuran-2(3H)?ones Reproduced from Ref. [46] with permission from the American Chemical Society

Scheme 31. Molybdenum-catalyzed selective preparation of halogenated olefin by olefin metathesis reaction Reproduced from Ref. [65] with permission from American Association for the Advancement of Science

Scheme 32. PEG-mediated recyclable borylative coupling of vinyl boronates with olefins Reproduced from Ref. [66] with permission from Elsevier Inc.

Scheme 33. Reaction of ozone/FeII-mediated dealkenylative alkenylation Reproduced from Ref. [67] with permission from John Wiley and Sons

Scheme 34. Ag-Ru heterobimetallic catalyzed selective semi- hydrogenation of alkynes Reproduced from Ref. [68] with permission from the American Chemical Society

Scheme 35. Ruthenium catalyzed E?selective semihydrogenation of alkynes Reproduced from Ref. [40] with permission from the American Chemical Society

Scheme 36. Pd3Pb/SiO2 and RhSb/SiO2 cocatalyzed one-pot E-olefin synthesis of alkynes Reproduced from Ref. [69] with permission from the American Chemical Society

Scheme 37. Pd and ZnI2 catalyzed selective semi-hydrogenation of alkynes Reproduced from Ref. [70] with permission from the American Chemical Society

Scheme 38. Palladium-catalyzed semi-hydrogenation of alkynes Reproduced from Ref. [43] with permission from John Wiley and Sons

Scheme 39. Phosphine-mediated semi-hydrogenation of alkynes Reproduced from Ref. [71] with permission from the Royal Society of Chemistry

Scheme 40. Ru-catalyzed selective semi-hydrogenation of alkynes Reproduced from Ref. [73] with permission from the Royal Society of Chemistry

Scheme 41. Preparation of trans-olefin by nickel-catalyzed semi- hydrogenation of alkynes Reproduced from Ref. [45] with permission from John Wiley and Sons

Scheme 42. Iron catalyzed hydrosilylation of alkynes Reproduced from Ref. [74] with permission from the American Chemical Society

Scheme 43. Phosphine mediated selective reduction of alkynes to E-alkenes Reproduced from Ref. [71] with permission from the Royal Society of Chemistry

Scheme 44. Mechanism of magnesium catalyzed borohydrogenation of alkynes Reproduced from Ref. [75] with permission from John Wiley and Sons

Scheme 45. Copper single-atom catalyst catalyzed hydroboration addition of alkynes Reproduced from Ref. [76] with permission from Elsevier Inc.

Scheme 46. Copper and palladium catalyzed series Sonogashira coupling and semi-reduction reaction Reproduced from Ref. [77] with permission from the American Chemical Society

Scheme 47. Palladium-catalyzed reductive coupling reaction of terminal alkynes with aryl iodides Reproduced from Ref. [78] with permission from John Wiley and Sons

Scheme 48. Copper and nickel catalyzed anti-markovnikov hydroalkylation of terminal alkynes Reproduced from Ref. [79] with permission from the American Chemical Society

Scheme 49. Cu-catalyzed stereoselective coupling of terminal alkynes and α-bromo carbonyls Reproduced from Ref. [80] with permission from the American Chemical Society

Scheme 50. Photocatalytic E-Z isomerization of styrenyl boron species Reproduced from Ref. [81] with permission from John Wiley and Sons

Scheme 51. Rhodium(I)-catalyzed defluorinative coupling of boronic acids with monofluoroalkenes Reproduced from Ref. [82] with permission from John Wiley and Sons

Scheme 52. Sc(OTf)3 catalyzed regioselective hydroboration of alkynes Reproduced from Ref. [83] with permission from the Royal Society of Chemistry

Scheme 53. Reaction of Fe-catalyzed selective hydrosilication Reproduced from Ref. [74] with permission from the American Chemical Society

Scheme 54. Iridium-catalyzed alkene-alkyne cross coupling reaction Reproduced from Ref. [84] with permission from the American Chemical Society

Scheme 55. Palladium-catalyzed formal hydroalkylation of aryl- substituted alkynes with hydrazones Reproduced from Ref. [85] with permission from John Wiley and Sons

Scheme 57. Phosphine-mediated three-component system of aldehydes, α-halo carbonyl compounds, and terminal alkenes Reproduced from Ref. [86] with permission from John Wiley and Sons

Scheme 57. Decarboxylative elimination of N?acyl amino acids via photoredox/cobalt dual catalysis Reproduced from Ref. [87] with permission from the American Chemical Society

Scheme 58. Blue light-promoted cross-coupling of aryldiazoacetates and diazocarbonyl compounds Reproduced from Ref. [88] with permission from the Royal Society of Chemistry

Scheme 59. Cobalt-catalyzed bromo-carboxydifluoromethyla- tion of alkynes Reproduced from Ref. [89] with permission from the Royal Society of Chemistry

Scheme 60. The addition of alkynes to ethyl difluoroiodoacetate under blue light Reproduced from Ref. [90] with permission from the American Chemical Society

Scheme 61. 2-Bromophenol catalyzed preparation of of alkenes by addition of alkynes Reproduced from Ref. [63] with permission from the Royal Society of Chemistry

Scheme 62. Copper catalyzed E-selective 1,1-diboration of terminal alkynes Reproduced from Ref. [91] with permission from the American Chemical Society

Scheme 63. Heteropalladium-catalyzed hydrosilylation of alkynes Reproduced from Ref. [92] with permission from Springer Nature

Scheme 64. Cu-catalyzed alkyne difunctionalization Reproduced from Ref. [93] with permission from the Chinese Chemical Society (CCS), Shanghai Institute of Organic Chemistry (SIOC), and the Royal Society of Chemistry

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多取代烯烃的Z∶E高选择性合成制备