Cross-Coupling of C—Si Bond by Using of Silyl Electrophiles

doi:10.6023/cjoc202108045

Chinese Journal of Organic Chemistry ›› 2022, Vol. 42 ›› Issue (2): 384-390.DOI: 10.6023/cjoc202108045 Previous Articles Next Articles

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硅亲电试剂参与碳硅交叉偶联反应研究进展

从思琪^a^,^b, 刘梦亚^a^,^b, 彭思远^b^,^c, 郑秋翠^b, 李梦娇^b, 郭艳^b, 罗斐贤^a^,^b^,^d^,^*()

a 中央民族大学民族地区生态环境国家民委重点实验室北京 100081
b 中央民族大学生命与环境科学学院北京 100081
c 首都师范大学化学系北京 100048
d 中央民族大学生物成像与系统生物学中心北京 100081

收稿日期:2021-08-23 修回日期:2021-09-16 发布日期:2022-02-24
通讯作者: 罗斐贤
作者简介:
^† 共同第一作者
基金资助:
北京市自然科学基金(2204091); 国家自然科学基金(21901263)

Cross-Coupling of C—Si Bond by Using of Silyl Electrophiles

Siqi Cong^a^,^b, Mengya Liu^a^,^b, Siyuan Peng^b^,^c, Qiucui Zheng^b, Mengjiao Li^b, Yan Guo^b, Feixian Luo^a^,^b^,^d()

a Key Laboratory of Ecology and Environment in Minority Areas (Minzu University of China), National Ethnic Affairs Commission, Beijing 100081
b College of Life and Environment Science, Minzu University of China, Beijing 100081
c Department of Chemistry, Capital Normal University, Beijing 100048
d Center for Bioimaging & System Biology, Minzu University of China, Beijing 100081

Received:2021-08-23 Revised:2021-09-16 Published:2022-02-24
Contact: Feixian Luo
About author:
^† These authors contributed equally to this work.
Supported by:
Beijing Natural Science Foundation(2204091); National Natural Science Foundation of China(21901263)

Organosilanes have been widely applied in synthetic chemistry, materials, pharmaceuticals, agrochemicals due to the special properties. The synthesis of organosilanes has been successfully developed by several strategies including nucleophilic substitution, hydrosilylation of alkene and C—H silylation. In recent years, significant achievements have been advanced in the cross-coupling of C—Si bond by using of silyl electrophiles, especially in the break-through of the reductive cross-coupling of silyl electrophiles and carbon electrophiles. It is emerging as one of the hottest issues in synthetic chemistry. In the review, the recent progress on the cross-coupling for C—Si bond formation by using of silyl electrophiles is summarized. The reaction type including silyl-Heck, silyl-Negishi, silyl-Kumada, silyl-reductive-electrophile-coupling, multicomponent coupling reaction and radical silylation was mainly discussed. In the meanwhile, the intramolecular C—Si coupling via demethylation of aryl silanes is also discussed.

Key words: silyl electrophile, cross-coupling, transition-metal catalyzed, organosilanes

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Siqi Cong, Mengya Liu, Siyuan Peng, Qiucui Zheng, Mengjiao Li, Yan Guo, Feixian Luo. Cross-Coupling of C—Si Bond by Using of Silyl Electrophiles[J]. Chinese Journal of Organic Chemistry, 2022, 42(2): 384-390.

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Fig. & Tab. 18

Scheme 1. Cross-coupling of Si—C bond

Scheme 2. Synthesis of silyl-Pt complex

Scheme 3. Pd-catalyzed cross-coupling of TMSI and styrene

Scheme 4. Pd-catalyzed cross-coupling of TMSI and alkene

Scheme 5. Pd-catalyzed cross-coupling of aryl alkene and Me2Si(OTf)2

Scheme 6. Pd-catalyzed cross-coupling of alkene and silyl halides

Scheme 7. Ni-catalyzed cross-coupling of aryl alkene and silyl triflates

Scheme 8. Ni-catalyzed cross-coupling of silyl chlorides and aryl alkenes

Scheme 9. Mn-catalyzed dehydrogenation Heck coupling of trialkyl silanes and alkenes

Scheme 10. Pd-catalyzed silyl-Negishi coupling of silyl iodides and organozinc reagents

Scheme 11. Pd-catalyzed silyl-Kumada coupling of silyl chlorides and Grignard reagents

Scheme 12. Ni-catalyzed reductive-electrophile-coupling of silyl chlorides and carbon electrophiles

Scheme 13. Ni-catalyzed reductive-electrophile-coupling of α- cyano alkyl triflates and silyl chlorides

Scheme 14. Pd-catalyzed coupling of terminal alkynes with TMSI and acetylenic tin reagents

Scheme 15. Pd-catalyzed coupling of alkynes with TMSI and organozinc reagents

Scheme 16. Electroreductive silyl chloride approach to radical silylation

Scheme 17. Pd-catalyzed intramolecular demethylation C—Si cross-coupling

Scheme 18. Catalytic cycle for Pd-catalyzed demethylation intramolecular C—Si coupling

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硅亲电试剂参与碳硅交叉偶联反应研究进展

Cross-Coupling of C—Si Bond by Using of Silyl Electrophiles

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Fig. & Tab. 18

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