Cross-Coupling of C-Si Bond by Using Silyl Reagents

doi:10.6023/cjoc201904024

Abstract

Organosilanes have been widely applied in synthetic chemistry, pharmaceuticals, agrochemicals, and materials due to the special properties. Several synthetic strategies including nucleophilic substitution, hydrosilylation of alkene, and C-H silylation have been developed. In recent years, significant progress has advanced in the cross-coupling of C-Si bond for the synthesis of organosilanes, especially in the break-through of the cross-coupling of C(sp³)-Si bond. It has become one of the hottest issues in synthetic chemistry. The recent progress on the cross-coupling of C-Si bond by using silyl reagents is summarized. The application of silyl reagents in cross-coupling for C-Si bond formation including silyl boranes, organosilyl magnesium, organosilyl zinc, unasymetric disilanes, organosilyl aluminum and organosilyl lithium reagents is mainly discussed.

Key words: silyl reagents, cross-coupling, transition-metal catalysis, organosilanes

Cite this article

Wang Mingfeng, Yu Maodong, Wang Wenshu, Lin Weili, Luo Feixian. Cross-Coupling of C-Si Bond by Using Silyl Reagents[J]. Chinese Journal of Organic Chemistry, 2019, 39(11): 3145-3153.

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Fig. & Tab. 24

Scheme 1. Cross-coupling of Si—C bond

Scheme 2. Ni/Cu-catalyzed silylation of pivalate via C—O activation

Scheme 3. Mechanism of Ni catalyzed silylation of C—O bond

Scheme 4. Ni-catalyzed cross-coupling of methoxyl aromatics and silyl boranes

Scheme 5. Pd-catalyzed cross-coupling of aromatic halides and silyl boranes

Scheme 6. Defluorosilylation of fluoroarenes and fluoroalkanes

Scheme 7. Defluorosilylation of gem-difluoroalkenes

Scheme 8. Base promoted defluorosilylation of fluoroarenes and fluoroalkanes

Scheme 9. Ni/Cu-catalyzed decarbonylative silylation of esters

Scheme 10. Pd-catalyzed cross-coupling of benzylic halides and silyl boranes

Scheme 11. Cu-catalyzed cross-coupling of alkyl aliphatic triflates and silyl boranes

Scheme 12. Cu-catalyzed cross-coupling of alkyl iodides and silyl boranes

Scheme 13. Cu-catalyzed cross-coupling of aliphatic carboxylic acid derivatives and silyl boranes

Scheme 14. Cu-catalyzed cross-coupling of α-triflyloxy nitriles or esters and silyl boranes

Scheme 15. Pd-catalyzed cross-coupling of allylic or vinyl phosphates and organosilyl magnesium reagents

Scheme 16. Fe/Co-catalyzed cross-coupling of alkyl bromides and organosilyl magnesium reagents

Scheme 17. Cu-catalyzed cross-coupling of allylic esters or carbamates and organosilyl zinc reagents

Scheme 18. Ni-catalyzed cross-coupling of alkyl bromides and organosilyl zinc reagents

Scheme 19. Cu-catalyzed cross-coupling of vinyliodonium salts and organosilyl zinc reagents

Scheme 20. Rh-catalyzed cross-coupling of nitriles and disilanes

Scheme 21. Pd-catalyzed cross-coupling of aromatic chlorides and silylsilatranes

Scheme 22. Pd-catalyzed cross-coupling of vinyl or allyl phosphates and organosilyl aluminum reagents

Scheme 23. Pd-catalyzed cross-coupling of aromatic bromides or vinyl iodides and organosilyl aluminum reagents

Scheme 24. Cross-coupling of aromatic bromides or vinyl iodides and organosilyl lithium reagents

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