SIOC English
有机化学
高级检索

有机化学 >

2023 , Vol. 43 >Issue 10: 3470 - 3490

DOI: https://doi.org/10.6023/cjoc202307017

综述与进展

无过渡金属参与的碳硅键构筑方法研究进展

  • 李奇阳 ,
  • 张海燕 ,
  • 刘文博
展开
  • 武汉大学化学与分子科学学院 武汉 430072

收稿日期: 2023-07-16

  修回日期: 2023-08-22

  网络出版日期: 2023-08-30

基金资助

国家重点研发计划(2022YFA1502902); 国家自然科学基金(22222111); 国家自然科学基金(21971198)

收起

Research Progress in Transition-Metal-Free C—Si Bond Formation

  • Qiyang Li ,
  • Haiyan Zhang ,
  • Wenbo Liu
Expand
  • College of Chemistry and Molecular Sciences, Wuhan University, Wuhan 430072
*E-mail:

Received date: 2023-07-16

  Revised date: 2023-08-22

  Online published: 2023-08-30

Supported by

National Key R&D Program of China(2022YFA1502902); National Nature Science Foundation of China(22222111); National Nature Science Foundation of China(21971198)

Fold

摘要

有机硅化合物在合成、制药和检测等许多领域有着广泛的应用. 鉴于其重要性, 有机硅化合物的合成方法学研究颇受关注. 其中, 在成本和环境友好性等方面的突出优势, 无过渡金属参与的碳硅键构筑作为过渡金属催化偶联策略的主要替代方法, 在过去几年中得到了发展并被应用于多种有机硅化合物的合成中. 以反应催化剂(引发剂)的种类为框架, 进一步按照反应中形成的碳硅键类型分类, 总结了近期发表的无过渡金属参与碳硅键构建方法, 对部分代表性的反应机理做了简要说明, 并对未来发展方向提出简要展望.

关键词： 无过渡金属; 碳硅键构筑; 有机硅; 绿色化学

本文引用格式

李奇阳 , 张海燕 , 刘文博 . 无过渡金属参与的碳硅键构筑方法研究进展[J]. 有机化学, 2023 , 43(10) : 3470 -3490 . DOI: 10.6023/cjoc202307017

Abstract

Organosilicons are widely used in many chemistry related fields. Given its important role, the chemical syntheses of organosilicon compounds have received considerable attention. Due to outstanding advantages in cost and environmental friendliness, transition-metal-free C—Si bond formation has been widely studied in the past decades and has been emerged as an important alternative to transition-metal-catalyzed C—Si cross-coupling. In this review, the recent developed methods of carbon-silicon bond formation under transition-metal-free conditions are summarized. The discussion is organized according to catalysts (acid catalysis, base catalysis, and radical initiation) and the types of C—Si bonds that formed. In addition, mechanistic discussions of representative reactions and a prospect for future development in this field are also briefly included.

Key words： transition-metal-free; C—Si bond formation; organosilicons, green chemistry

参考文献

[1]
Brook M. A. Silicon in Organic, Organometallic, and Polymer Chemistry, Wiley, New York, 2000.
[2]
Franz A. K.; Wilson S. O. J. Med. Chem. 2013, 56, 388.
[3]
(a) Feng S.-Y.; Qu Z.-R.; Zhou Z.-K.; Chen J.-Y.; Gai L.-Z.; Lu H.; Chem. Commun. 2021, 57, 11689.
[3]
(b) Salgues B.; Sarkar R.; Fajri M. L.; Avalos-Quiroz Y. A.; Manick A.; Giorgi M.; Vanthuyne N.; Carissan Y.; Videlot- Ackermann C.; Ackermann J.; Canard G.; Parrain J.; Guennic B. L.; Jacquemin D.; Amatore M.; Commeiras L.; Zaborova E.; Fages F. J. Org. Chem. 2022, 87, 3276.
[4]
(a) Poole C. F. J. Chromatogr. A 2013, 1296, 2.
[4]
(b) Hsieh C.-Z.; Chung W.-H.; Ding W.-H. RSC Adv. 2021, 11, 23607.
[5]
(a) Mets?nen T. T.; Gallego D.; Szilvási T.; Driess M.; Oestreich M. Chem. Sci. 2015, 6, 7143.
[5]
(b) Bleith T.; Gade L. H. J. Am. Chem. Soc. 2016, 138, 6074.
[5]
(c) Park S.; Chang S. Angew. Chem., Int. Ed. 2017, 56, 7720.
[6]
Muramatsu W.; Yamamoto H. J. Am. Chem. Soc. 2021, 143, 6792.
[7]
Bellan A. B.; Knochel P. Angew. Chem., Int. Ed. 2019, 58, 1838.
[8]
McWilliams S. F.; Broere D. L. J.; Halliday C. J. V.; Bhutto S. M.; Mercado B. Q.; Holland P. L. Nature 2020, 584, 221.
[9]
(a) Verma V.; Koperniku A.; Edwards P. M.; Schafer L. L. Chem. Commun. 2022, 58, 9174.
[9]
(b) Kuci'nski K.; Stachowiak H.; Lewandowski D.; Gruszczy'nski M.; Lampasiak P.; Hreczycho G. J. Organomet. Chem. 2022, 961, 122127.
[9]
(c) Matsuoka K.; Komami N.; Kojima M.; Mita T.; Suzuki K.; Maeda S.; Yoshino T.; Matsunaga S. J. Am. Chem. Soc. 2021, 143, 103.
[10]
(a) Langkopf E.; Schinzer D. Chem. Rev. 1995, 95, 1375.
[10]
(b) Chatgilialoglu C.; Ferreri C.; Landais Y.; Timokhin V. I. Chem. Rev. 2018, 118, 6516.
[11]
Littleson M. M.; Campbell A. D.; Clarke A.; Dow M.; Ensor G.; Evans M. C.; Herring A.; Jackson B. A.; Jackson L. V.; Karlsson S.; Klauber D. J.; Legg D. H.; Leslie K. W.; Moravc?ík S?.; Parsons C. D.; Ronson T. O.; Meadows R. E. Org. Process Res. Dev. 2019, 23, 1407.
[12]
Komiyama T.; Minami Y.; Hiyama T. ACS Catal. 2017, 7, 631.
[13]
(a) Yang Y.-H.; Wang C.-Y. Sci. China Chem. 2015, 58, 1266.
[13]
(b) Lipke M. C.; Liberman-Martin A. L.; Tilley T. D. Angew. Chem., Int. Ed. 2017, 56, 2260.
[14]
Schuman D. P.; Liu W.-B.; Nesnas N.; Stoltz B. M. Organosilicon Chemistry: Novel Approaches and Reactions, Eds.: Hiyama, T.; Oestreich, M., Wiley-VCH Verlag GmbH & Co. KGaA, New York, 2019.
[15]
Tyagi A.; Yadav N.; Khan J.; Singh S.; Hazra C. K. Asian J. Org. Chem. 2021, 10, 334.
[16]
B?hr S.; Oestreich M. Angew. Chem., Int. Ed. 2017, 56, 52.
[17]
Gandhamsetty N.; Joung S.; Park S.-W.; Park S.; Chang S. J. Am. Chem. Soc. 2014, 136, 16780.
[18]
Gandhamsetty N.; Park S.; Chang S. J. Am. Chem. Soc. 2015, 137, 15176.
[19]
Hazra C. K.; Gandhamsetty N.; Park S.; Chang S. Nat. Commun. 2016, 7, 13431.
[20]
Gandhamsetty N. Park J.; Jeong J.; Park S.-W.; Park S.; Chang S. Angew. Chem., Int. Ed. 2015, 54, 6832.
[21]
Kim E.; Park S.; Chang S. Chem. Eur. J. 2018, 24, 5765.
[22]
Pérez M.; Hounjet L.; Caputo C.; Dobrovetsky R.; Stephan D. J. Am. Chem. Soc. 2013, 135, 18308.
[23]
Andrews R.; Chitnis S.; Stephan D. Chem. Commun. 2019, 55, 5599
[24]
Parks D.; Blackwell J.; Piers W. J. Org. Chem. 2000, 65, 3090
[25]
He T.; W, G.-Q.; Long P.-W.; Kemper S.; Irran E.; Klare H. F. T.; Oestreich M. Chem. Sci. 2021, 12, 569.
[26]
Fang H.-Q.; Xie K.X.; Kemper S.; Oestreich M. Angew. Chem., Int. Ed. 2021, 60, 8542.
[27]
Ma Y.-H.; Wang B.-L.; Zhang L.; Hou Z.-M. J. Am. Chem. Soc. 2016, 138, 3663.
[28]
Han Y.-X.; Zhang S.-T.; He J.-H.; Zhang Y.-T. J. Am. Chem. Soc. 2017, 139, 7399.
[29]
Han Y.-X.; Zhang S.; He J.-H.; Zhang Y.-T. ACS Catal. 2018, 8, 8765.
[30]
Zhang J.-B.; Park S.; Chang S. J. Am. Chem. Soc. 2018, 140, 13209.
[31]
Ma Y.-H.; Lou S.-J.; Luo G.; Luo Y.; Zhan G.; Nishiura M.; Luo Y.; Hou Z.-M. Angew. Chem., Int. Ed. 2018, 57, 15222.
[32]
Sasaki M.; Kondo Y. Org. Lett. 2015, 17, 848.
[33]
Toutov A.; Liu W.-B.; Betz K. N.; Fedorov A.; Stoltz B. M.; Grubbs R. H. Nature 2015, 518, 80.
[34]
Banerjee S.; Yang Y.-F.; Jenkins I. D.; Liang Y.; Toutov A. A.; Liu W.-B.; Schuman D. P.; Grubbs R. H.; Stoltz B. M.; Krenske E. H.; Houk K. N.; Zare R. N. J. Am. Chem. Soc. 2017, 139, 6880.
[35]
Liu W.-B.; Schuman D. P.; Yang Y.-F.; Toutov A. A.; Liang Y.; Klare H. F. T.; Nesnas N.; Oestreich M.; Blackmond D. G.; Virgil S. C.; Banerjee S.; Zare R. N.; Grubbs R. H.; Houk K. N.; Stoltz B. M. J. Am. Chem. Soc. 2017, 139, 6867.
[36]
Gu Y.-T.; Shen Y.-Y.; Zarate C.; Martin R. J. Am. Chem. Soc. 2019, 141, 127.
[37]
Toutov A. A.; Betz K. N.; Schuman D. P.; Liu W.-B.; Fedorov A.; Stoltz B. M.; Grubbs R. H. J. Am. Chem. Soc. 2017, 139, 1668.
[38]
Nozawa-Kumada K.; Inagi M.; Kondo Y. Asian J. Org. Chem. 2017, 6, 63.
[39]
Neil B.; Lucien F.; Fensterbank L.; Chauvier C. ACS Catal. 2021, 11, 13085.
[40]
Wang L.; Zhang T.; Sun W.; He Z.-Y.; Xia C.-G.; Lan Y.; Liu C. J. Am. Chem. Soc. 2017, 139, 5257.
[41]
Qi W.-Y.; Zhen J.-S.; Xu X.-H.; Du X.; Li Y.-H.; Yuan H.; Guan Y.-S.; We X.; Wang Z.-Y.; Liang G.-H.; Luo Y. Org. Lett. 2021, 23, 5988.
[42]
Liu X.-W.; Zarate C.; Martin R. Angew. Chem., Int. Ed. 2019, 58, 2064.
[43]
Mallick S.; Xu P.; Wgrthwein E.; Studer A. Angew. Chem., Int. Ed. 2019, 58, 283.
[44]
Oestreich M.; Hartmann E.; Mewald M. Chem. Rev. 2013, 113, 402.
[45]
Ito H.; Horit Y.; Yamamoto E. Chem. Commun. 2012, 48, 8006.
[46]
Morimasa Y.; Kabasawa K.; Ohmura T.; Suginome M. Asian J. Org. Chem. 2019, 8, 1092.
[47]
Nagao K.; Ohmiya H.; Sawamura M. Org. Lett. 2015, 17, 1304.
[48]
Gu Y.-T.; Duan Y.-Y.; Shen Y.-Y.; Martin R. Angew. Chem., Int. Ed. 2020, 59, 2061.
[49]
Jeong E.; Heo J.; Jin S.; Kim D.; Chang S. ACS Catal. 2022, 12, 4898.
[50]
Huo Y.-W.; Shen P.-P.; Duan W.-Z.; Zhen C.; Song C.; Ma Y.-D. Chin. Chem. Lett. 2018, 29, 1359.
[51]
Li T.-T.; Wu Y.-Z.; Duan W.-Z.; Ma Y.-D. RSC Adv. 2021, 11, 17860.
[52]
Xu P.; Würthwein E.; Daniliuc C.; Studer A. Angew. Chem., Int. Ed. 2017, 56, 13872.
[53]
Wang X.; Yu Z.-X.; Liu W.-B. Org. Lett. 2022, 24, 8735.
[54]
Shang X.-J.; Liu Z.-Q. Org. Biomol. Chem. 2016, 14, 7829.
[55]
Chatgilialoglu C.; Ferreri C.; Landais Y.; Timokhin V. I. Chem. Rev. 2018, 118, 6516.
[56]
Zhang X.-P.; Fang J.-K.; Cai C.; Lu G.-P. Chin. Chem. Lett. 2021, 32, 1280.
[57]
Li J.-S.; Wu J. ChemPhotoChem 2018, 2, 839.
[58]
Ren L.-Q.; Li N.; Ke J.; He C. Org. Chem. Front. 2022, 9, 6400.
[59]
Sakamoto R.; Nguyen B.; Maruoka K. Asian J. Org. Chem. 2018, 7, 1085.
[60]
Chang X.-H.; Wang Z.-L.; Zhao M.; Yang C.; Li J.-J.; Ma W.-W.; Xu Y.-H. Org. Lett. 2020, 22, 1326.
[61]
Leifert D.; Studer A. Org. Lett. 2015, 17, 386.
[62]
Studer A.; Curran D. P. Nat. Chem. 2014, 6, 765.
[63]
Lin Y.-M.; Lu G.-P.; Wang R.-K.; Yi W.-B. Org. Lett. 2017, 19, 1100.
[64]
Yang Y.; Song R.-J.; Li Y.; Ouyang X.-H.; Li J.-H.; He D.-L. Chem. Commun. 2018, 54, 1441.
[65]
Zhang C.; Pi J.-X.; Wang L.; Liu P.; Sun P.-P. Org. Biomol. Chem. 2018, 16, 9223.
[66]
Zhang T.-Y.; Zheng S.-H.; Kobayashi T.; Maekawa H. Org. Lett. 2021, 23, 7129.
[67]
Asgari P.; Hua Y.-D.; Bokka A.; Thiamsiri C.; Prasitwatcharakorn W.; Karedath A.; Chen X.; Sardar S.; Yum K.; Leem G.; Pierce B. S.; Nam K.; Gao J.-L.; Jeon J. Nat. Catal. 2019, 2, 164.
[68]
Buch F.; Brettar J.; Harder S. Angew. Chem., Int. Ed. 2006, 45, 2741.
[69]
Leich V.; Spaniol T.; Maron L.; Okuda J. Chem. Commun. 2014, 50, 2311
[70]
Schuhknecht D.; Spaniol T.; Maron L.; Okuda J. Angew. Chem., Int. Ed. 2020, 59, 310.
[71]
Liu Z.-Z.; Shi X.-H.; Cheng J.-H. Dalton Trans. 2020, 49, 8340.
[72]
Zhao L.-X.; Shi X.-H.; Cheng J.-H. ACS Catal. 2021, 11, 2041.
[73]
Gong X.; Deng P.; Cheng J.-H. ChemCatChem 2022, 14, e202200060.
[74]
Li T.; McCabe K. N.; Maron L.; Leng X.-B.; Chen Y.-F. ACS Catal. 2021, 11, 6348.
[75]
Liu R.-X.; Liu X.-J.; Cheng T.-Y.; Chen Y.-F. Eur. J. Org. Chem. 2022, 1, e202101218.
[76]
Li T.; Liu R.-X.; Liu X.-J.; Chen Y.-F. Org. Lett. 2023, 25, 761
[77]
Wang L.-L.; Li Y.-H.; Li Z.-F.; Kira M. Coord. Chem. Rev. 2022, 457, 214413.
Options
文章导航

/

〈 〉