Research Progress of Transition Metal-Catalyzed Synthesis of 1,3-Conjugated Dienyl Boron Compounds

doi:10.6023/cjoc202310008

Abstract

1,3-Dienyl boron compounds have important applications in the modification of biologically active molecules and organic synthesis. It can be used as an organoboron reagent to construct a new organic framework by Suzuki reaction, and and can also undergo Diels-Alder reaction to prepare boron substituted cycloolefin intermediates. At present, the synthesis of 1,3-conjugated dienyl boron compounds is mainly achieved through the cross-coupling reaction of organometallic reagents to alkynes or olefin catalyzed by transition metals, the Heck reaction of borates to olefin, the hydroboration of alkynes and the carboboration of alkynes. The synthesis of 1,3-conjugated dienyl boron compounds is reviewed by classification based on different reaction types catalyzed by transition metals, and its development prospects are prospected.

Key words: transition metal, catalysis, 1,3-conjugated dienyl boron, hydroboration, carboboration

Cite this article

Guangli Xu, Hongping Han, Luwei Cao, Simin Hong, linyue Hai, Xiang Cui. Research Progress of Transition Metal-Catalyzed Synthesis of 1,3-Conjugated Dienyl Boron Compounds[J]. Chinese Journal of Organic Chemistry, 2024, 44(5): 1480-1493.

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Fig. & Tab. 22

Figure 1. Conjugated alkenes natural products

Scheme 1. Palladium-catalyzed Heck reaction of alkenyl boron with alkenyl iodine to synthesize 1,3-conjugated dienyl boron compounds

Scheme 2. Palladium-catalyzed Stille coupling reaction to synthesize 1,3-conjugated dienyl boron compounds

Scheme 3. Palladium-catalyzed difunctional reaction of alkyne involving organozirconium reagent to synthesize 1,3-conjugated dienyl boron compounds

Scheme 4. Palladium-catalyzed Negishi coupling reaction involving organozinc reagents to synthesize 1,3-conjugated dienyl boron compounds

Scheme 5. Palladium-catalyzed difunctional reaction of alkyne involving borosilicon reagent to synthesize 1,3-conjugated dienyl boron compounds

Scheme 6. Palladium-catalyzed hydroboration of alkyne to synthesize 1,3-conjugated dienyl boron compounds

Scheme 7. Copper-catalyzed hydroboration of enyl to synthesize 1,3-conjugated dienyl boron compounds

Scheme 8. Copper-catalyzed hydroboration of substituted alkyne to synthesize 1,3-conjugated dienyl boron compounds

Scheme 9. Copper-catalyzed hydroboration of alkyne to synthesize 1,3-conjugated dienyl boron compounds

Scheme 10. Cobalt-catalyzed hydrogenation cyclization of 1,6-diynylboron to synthesize 1,3-conjugated dienyl boron com- pounds

Scheme 11. Copper-catalyzed carboboration of olefin acetylene to synthesize 1,3-conjugated dienyl boron compounds

Scheme 12. Copper-catalyzed carboboration of alkyne to synthesize 1,3-conjugated dienyl boron compounds

Scheme 13. Cu/Pd-catalyzed alkenylboration of alkynes with alkenyl bromides and bis(pinacolato)diboron to synthesize 1,3-conjugated dienyl boron compounds

Scheme 14. Cu/Pd-catalyzed bifunctional reaction of alkynes to synthesize 1,3-conjugated dienyl boron compounds

Scheme 15. Ruthenium-catalyzed cross-reduction coupling reaction of alkenes and alkynes to synthesize 1,3-conjugated dienyl boron compounds

Scheme 16. Ruthenium-catalyzed cross-reduction coupling reaction of alkenes and alkynes to synthesize 1,3-conjugated dienyl boron compounds

Scheme 17. Palladium-catalyzed dehydroborylation of conjugated dienes to synthesize 1,3-conjugated dienyl boron compounds

Scheme 18. Ruthenium-catalyzed metathesis reaction of olefin to synthesize 1,3-conjugated dienyl boron compounds

Scheme 19. Copper-catalyzed ring-opening defluoroboronation reaction of difluorocyclobutene to synthesize 1,3-conjugated dienyl boron compounds

Scheme 20. Nickel-catalyzed hydroboration of olefin to synthesize 1,3-conjugated dienyl boron compounds

Scheme 21. Nickel-catalyzed reduction coupling of alkenyl electrophiles to synthesize 1,3-conjugated dienyl boron compounds

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过渡金属催化1,3-共轭二烯基硼化合物合成研究进展