硅亲电试剂参与碳硅交叉偶联反应研究进展

doi:10.6023/cjoc202108045

有机化学 ›› 2022, Vol. 42 ›› Issue (2): 384-390.DOI: 10.6023/cjoc202108045 上一篇下一篇

综述与进展

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)

文章分享

摘要/Abstract

有机硅化合物因其特殊的性质而广泛应用于合成化学、材料、药物和农药化学等领域. 有机硅化合物通常由亲核取代、烯烃硅氢化和碳氢键直接硅化等方法制备. 近年来, 通过交叉偶联构建碳硅键合成有机硅烷取得突破性进展, 引起合成化学领域研究者的广泛关注和兴趣, 成为有机硅化合物合成研究热点. 主要从硅亲电试剂参与的Heck反应、Negishi反应、Kumada反应、最新突破的还原交叉偶联反应以及多组分偶联反应和自由基硅化反应, 总结了近些年来廉价易得的有机硅亲电试剂参与交叉偶联合成有机硅烷研究进展. 同时介绍了芳基硅脱甲基分子内交叉偶联反应相关研究进展.

关键词: 硅亲电试剂, 交叉偶联, 过渡金属催化, 有机硅化合物

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

引用此文

从思琪, 刘梦亚, 彭思远, 郑秋翠, 李梦娇, 郭艳, 罗斐贤. 硅亲电试剂参与碳硅交叉偶联反应研究进展[J]. 有机化学, 2022, 42(2): 384-390.

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.

导出引用 EndNote|Reference Manager|ProCite|BibTeX|RefWorks

分享此文

图/表 18

图式1. 交叉偶联构建碳硅键

Scheme 1. Cross-coupling of Si—C bond

图式2. 硅基铂配合物合成

Scheme 2. Synthesis of silyl-Pt complex

图式3. 钯催化三甲基碘硅烷与苯乙烯交叉偶联

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

图式4. Pd催化TMSI与烯烃交叉偶联

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

图式5. 钯催化芳基烯烃与二甲基硅双三氟甲磺酸酯偶联

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

图式6. 钯催化烯烃与卤代硅烷偶联

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

图式7. 镍催化芳基烯烃与三氟甲磺酸硅脂偶联

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

图式8. 镍催化氯硅烷与烯烃偶联反应

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

图式9. 锰催化三烷基硅烷与烯烃脱氢Heck偶联

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

图式10. 钯催化碘硅烷与有机锌试剂的类Negishi反应

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

图式11. 钯催化氯硅烷与格氏试剂Kumada偶联

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

图式12. 镍催化烯基卤代硅与碳亲电试剂还原偶联

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

图式13. 镍催化卤代硅与α-氰基三氟甲磺酸烷酯还原偶联

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

图式14. 钯催化碘代硅与炔基锡和端炔试剂偶联反应

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

图式15. 钯催化碘代硅与有机锌和内炔偶联反应

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

图式16. 电还原氯硅烷实现自由基硅化反应

Scheme 16. Electroreductive silyl chloride approach to radical silylation

图式17. 钯催化芳基硅脱甲基分子内C—Si交叉偶联

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

图式18. 钯催化三甲基芳基硅脱甲基分子内硅化反应机理

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

参考文献 29

[1]	Brook, M. A. Silicon in Organic, Organometallic, and Polymer Chemistry, Wiley, New York, 2000, Chapter 5.
[2]	(a) Tondreau, A. M.; Atienza, C. C. H.; Weller, K. J.; Nye, S. A.; Lewis, K. M.; Delis, J. G. P.; Chirik, P. J. Science 2012, 335, 567. doi: 10.1126/science.1214451 pmid: 28654260
	(b) Peng, D.; Zhang, Y.; Du, X.; Zhang, L.; Leng, X., Walter, M. D.; Huang, Z. J. Am. Chem. Soc. 2013, 135, 19154. doi: 10.1021/ja404963f pmid: 28654260
	(c) Buslov, I.; Becouse, J.; Mazza, S.; Montandon-Clerc, M.; Hu, X. Angew. Chem., Int. Ed. 2015, 54, 14523. doi: 10.1002/anie.v54.48 pmid: 28654260
	(d) Chen, J.; Cheng, B.; Cao, M.; Lu, Z. Angew. Chem., Int. Ed. 2015, 54, 4661. doi: 10.1002/anie.201411884 pmid: 28654260
	(e) Sun, J.; Deng, L. ACS Catal. 2016, 6, 290. doi: 10.1021/acscatal.5b02308 pmid: 28654260
	(f) Cheng, B.; Lu, P.; Zhang, H.; Cheng, X.; Lu, Z. J. Am. Chem. Soc. 2017, 139, 9439. doi: 10.1021/jacs.7b04137 pmid: 28654260
	(g) Yang, Y.; Song, R.-J.; Li, Y.; Ouyang, X.-H.; Li, J.-H.; He, D.-L. Chem. Commun. 2018, 54, 1441. doi: 10.1039/C7CC08964C pmid: 28654260
	(h) Liu, J.; Chen, W.; Li, J.; Cui, C. ACS Catal. 2018, 8, 2230. doi: 10.1021/acscatal.8b00010 pmid: 28654260
	(i) Huai, G. Z.; Teng, H.-L.; Luo, Y.; Lou, S.-J.; Nishiura, M.; Hou, Z. Angew. Chem., Int. Ed. 2018, 57, 12342. doi: 10.1002/anie.201807493 pmid: 28654260
[3]	(a) Cheng, C.; Hartwig, J. F. Chem. Rev. 2015, 115, 8946. doi: 10.1021/cr5006414 pmid: 25714857
	(b) Toutov, A. A.; Liu, W.-B.; Betz, K. N.; Fedorov, A.; Stoltz, B. M.; Grubbs, R. H. Nature 2015, 518, 80. doi: 10.1038/nature14126 pmid: 25714857
	(c) Tobisu, M.; Onoe, M.; Yusuke Kita, Y.; Chatani, N. J. Am. Chem. Soc. 2009, 131, 7506. doi: 10.1021/ja9022978 pmid: 25714857
	(d) Ihara, H.; Suginome, M. J. Am. Chem. Soc. 2009, 131, 7502. doi: 10.1021/ja902314v pmid: 25714857
	(e) Onoe, M.; Baba, K.; Kim, Y.; Kita, Y.; Mamoru Tobisu, M.; Chatani, N. J. Am. Chem. Soc. 2012, 134, 19477. doi: 10.1021/ja3096174 pmid: 25714857
	(f) Liang, Y.; Geng, W.; Wei, J.; Xi, Z. Angew. Chem., Int. Ed. 2012, 51, 1934. doi: 10.1002/anie.v51.8 pmid: 25714857
	(g) Ghavtadze, N.; Melkonyan, F. S.; Gulevich, A. V.; Huang, C.; Gevorgyan, V. Nat. Chem. 2014, 6. 122. doi: 10.1038/nchem.1841 pmid: 25714857
	(h) Kanyiva, K. S.; Kuninobu, Y.; Kanai, M. Org. Lett. 2014, 16, 1968. doi: 10.1021/ol500519y pmid: 25714857
	(i) Liu, Y. J.; Liu, Y. H.; Zhang, Z. Z.; Yan, S. Y.; Chen, K.; Shi, B. F. Angew. Chem., Int. Ed. 2016, 55, 13859. doi: 10.1002/anie.201607766 pmid: 25714857
	(j) Li, W.; Huang, X.; You, J. Org. Lett. 2016, 18, 666. doi: 10.1021/acs.orglett.5b03593 pmid: 25714857
	(k) Zhao, W.-T.; Lu, Z.-Q.; Zheng, H.; Xue, X.-S.; Zhao, D. ACS Catal. 2018, 8, 7997. doi: 10.1021/acscatal.8b01992 pmid: 25714857
[4]	Database of iBonD 2.0, http://ibond.nankai.edu.cn/bde/#
[5]	(a) Korch, K. M.; Watson, D. A. Chem. Rev. 2019, 119, 8192. doi: 10.1021/acs.chemrev.8b00628
	(b) Bähr, S.; Xue, W.; Oestreich, M. ACS Catal. 2019, 9, 16. doi: 10.1021/acscatal.8b04230
	(c) Murakami, K.; Hirano, K.; Yorimitsu, H.; Oshima, K. Angew. Chem., Int. Ed. 2008, 47, 5833. doi: 10.1002/anie.200801949
	(d) Zhang, Q. W.; An, K.; He, W. Angew. Chem., Int. Ed. 2014, 53, 5667. doi: 10.1002/anie.v53.22
	(e) Li, L. W.; Zhang, Y. B.; Gao, L.; Song, Z. L. Tetrahedron Lett. 2015, 56, 1466. doi: 10.1016/j.tetlet.2015.01.184
	(f) Zhang, L.; Hang, Z.; Liu, Z.-Q. Angew. Chem., Int. Ed. 2016, 55, 236. doi: 10.1002/anie.201509537
	(g) Xu, Z.; Xu, J. Z.; Zhang, J.; Zheng, Z. J.; Cao, J.; Cui, Y. M.; Xu, L. W. Chem. Asian J. 2017, 12, 1749. doi: 10.1002/asia.v12.14
	(h) Li, W.; Xiao, G.; Deng, G.; Liang, Y. Org. Chem. Front. 2018, 5, 1488. doi: 10.1039/C8QO00189H
[6]	(a) Duan, J.; Wang, K.; Xu, G.-L.; Kang, S.; Qi, L.; Liu, X.-Y.; Shu, X.-Z. Angew. Chem., nt. Ed. 2020, 59, 23083. doi: 10.1002/anie.v59.51
	(b) Zhang, L.; Oestreich, M. Angew. Chem., Int. Ed. 2021, 60, 18587. doi: 10.1002/anie.v60.34
[7]	Wang, M.-F.; Yu, M.-D.; Wang, W.-S.; Lin, W.-L.; Luo, F.-X. Chin. J. Org. Chem. 2019, 39, 3145. (in Chinese) doi: 10.6023/cjoc201904024
	( 王明凤, 余茂栋, 王文蜀, 林伟立, 罗斐贤, 有机化学, 2019, 39, 3145.) doi: 10.6023/cjoc201904024
[8]	Kuyper, J. Inorg. Chem. 1978. 17, 77. doi: 10.1021/ic50179a017
[9]	Yamashita, H.; Hayashi, T.; Kobayashi, T.; Tanaka, M.; Goto M. J. Am. Chem. Soc. 1988, 110, 4417. doi: 10.1021/ja00221a053
[10]	Yamashita, H.; Kobayashi, T.; Hayashi, T.; Tanaka, M. Chem. Lett. 1990, 19, 1447. doi: 10.1246/cl.1990.1447
[11]	Mitton, S.J.; McDonald, R.; Turculet, L. Organometallics 2009, 28, 5122. doi: 10.1021/om9003863
[12]	Yamashita, H.; Kobayashi, T.-A.; Hayashi, T.; Tanaka, M. Chem. Lett. 1991. 20, 761. doi: 10.1246/cl.1991.761
[13]	McAtee, J. R.; Martin, S. E.; Ahneman, D. T.; Johnson, K. A.; Watson, D. A. Angew. Chem., Int. Ed. 2012, 51, 3663. doi: 10.1002/anie.v51.15
[14]	Watson, D.; Martin, S. Synlett 2013, 24, 2177. doi: 10.1055/s-0033-1339795 pmid: 29104371
[15]	Martin, S. E.; Watson, D. A. J. Am. Chem. Soc. 2013, 135, 13330. doi: 10.1021/ja407748z pmid: 23984876
[16]	McAtee, J. R.; Yap, G. P. A.; Watson, D. A. J. Am. Chem. Soc. 2014, 136, 10166. doi: 10.1021/ja505446y pmid: 25003502
[17]	Krause, S. B.; McAtee, J. R.; Yap, G. P. A.; Watson, D. A. Org. Lett. 2017, 19, 5641. doi: 10.1021/acs.orglett.7b02807 pmid: 28960083
[18]	McAtee, J. R.; Krause, S. B.; Watson, D. A. Adv. Synth. Catal. 2015, 357, 2317. pmid: 27325912
[19]	McAtee, J. R.; Martin, S. E.; Cinderella, A. P.; Reid, W. B.; Johnson, K. A.; Watson, D. A. Tetrahedron 2014, 70, 4250. pmid: 24914247
[20]	Matsumoto, K.; Huang, J.; Naganawa, Y.; Guo, H.; Beppu, T.; Sato, K.; Shimada, S.; Nakajima, Y. Org. Lett. 2018, 20, 2481. doi: 10.1021/acs.orglett.8b00847 pmid: 29617139
[21]	Dong, J.; Yuan, X. A.; Yan, Z.; Mu, L.; Ma, J.; Zhu, C.; Xie, J. Nat. Chem. 2021, 13, 182. doi: 10.1038/s41557-020-00589-8 pmid: 33318674
[22]	Cinderella, A. P.; Vulovic, B.; Watson, D. A. J. Am. Chem. Soc. 2017, 139, 7741. doi: 10.1021/jacs.7b04364 pmid: 28570065
[23]	Vulovic, B.; Cinderella, A. P.; Watson, D. A. ACS Cat. 2017, 7, 8113. doi: 10.1021/acscatal.7b03465
[24]	Chatani, N.; Amishiro, N.; Murai, S. J. Am. Chem. Soc. 1991, 113, 7778.
[25]	Chatani, N.; Amishiro, N.; Morii, T.; Yamashita, T.; Murai, S. J. Org. Chem. 1995, 60, 1834. doi: 10.1021/jo00111a048
[26]	Wisthoff, M. F.; Pawley, S. B.; Cinderella, A. P.; Watson, D. A. J. Am. Chem. Soc. 2020, 142, 12051. doi: 10.1021/jacs.0c05382 pmid: 32579845
[27]	(a) Shang, X.; Liu, Z. Q. Org. Biomol. Chem. 2016, 14, 7829. doi: 10.1039/C6OB00797J
	(b) Li, J.-S.; Wu, J. ChemPhotoChem 2018, 2, 839. doi: 10.1002/cptc.v2.10
[28]	Lu, L.; Siu, J.; Lai, Y.; Lin, S. J. Am. Chem. Soc. 2020, 142, 21272. doi: 10.1021/jacs.0c10899
[29]	Liang, Y.; Zhang, S.; Xi, Z. J. Am. Chem. Soc. 2011, 133, 9204. doi: 10.1021/ja2024959 pmid: 21517096

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

RichHTML

PDF

可视化

摘要/Abstract

引用此文

分享此文

图/表 18

参考文献 29

相关文章 15

编辑推荐

相关统计

本文评价

[1]	赵红琼, 于淼, 宋冬雪, 贾琦, 刘颖杰, 季宇彬, 许颖. 羧酸脱羧羟基化反应研究进展[J]. 有机化学, 2024, 44(1): 70-84.
[2]	童红恩, 郭宏宇, 周荣. 可见光促进惰性碳-氢键对羰基的加成反应进展[J]. 有机化学, 2024, 44(1): 54-69.
[3]	蒋宜欣, 唐伯孝, 毛海波, 陈雪霞, 俞洋杰, 全翠英, 徐昭阳, 石金慧, 刘益林. 水-聚乙二醇(PEG-200)中烯烃与碘代芳烃绿色可循环无负载偶联反应的研究[J]. 有机化学, 2023, 43(9): 3210-3215.
[4]	高晓阳, 翟锐锐, 陈训, 王烁今. 碳酸亚乙烯酯参与C—H键活化反应的研究进展[J]. 有机化学, 2023, 43(9): 3119-3134.
[5]	赵瑜, 张凯, 白育斌, 张琰图, 史时辉. 无金属条件下可见光催化与溴盐协同促进烯烃的氢硅化反应研究[J]. 有机化学, 2023, 43(8): 2837-2847.
[6]	杨晓娜, 郭宏宇, 周荣. 可见光促进有机硅化合物参与的化学转化[J]. 有机化学, 2023, 43(8): 2720-2742.
[7]	陈新强, 张敬. 伯醇的脱羟甲基反应的研究进展[J]. 有机化学, 2023, 43(8): 2711-2719.
[8]	徐光利, 许静, 徐海东, 崔香, 舒兴中. 过渡金属催化烯烃和炔烃合成1,3-共轭二烯化合物研究进展[J]. 有机化学, 2023, 43(6): 1899-1933.
[9]	户晓兢, 郭斐翔, 朱润青, 周柄棋, 张涛, 房立真. 对烷氧基酚的合成及其去芳构化后的合成应用[J]. 有机化学, 2023, 43(6): 2239-2244.
[10]	庞明杨, 常宏宏, 冯璋, 张娟. 过渡金属催化吲哚的串联去芳构化反应研究进展[J]. 有机化学, 2023, 43(4): 1271-1291.
[11]	童宇星, 王子维, 刘奔, 徐耀威, 高颂, 唐向兵, 张兴华. 吲哚-3-硫醚类化合物的合成研究进展[J]. 有机化学, 2023, 43(4): 1310-1324.
[12]	蒙玲, 汪君. 硫代黄烷酮类衍生物的合成研究进展[J]. 有机化学, 2023, 43(3): 873-891.
[13]	段康慧, 唐俊龙, 伍婉卿. 稠杂环化合物的合成及其抗肿瘤活性研究进展[J]. 有机化学, 2023, 43(3): 826-854.
[14]	贾海瑞, 邱早早. 过渡金属催化硼-氢键活化合成含硼-杂原子键邻碳硼烷衍生物的研究进展[J]. 有机化学, 2023, 43(3): 1045-1068.
[15]	吴孔川, 卢铠洪, 林建斌, 张慧君. 莱啉酰亚胺类化合物的邻位C—H键功能化研究进展[J]. 有机化学, 2023, 43(3): 1000-1011.