三甲基硅基(TMS)化学:C(sp3)-Si键的催化活化

杨琪; 欧阳昆冰; 刘亮; 席振峰

doi:10.7536/PC171237

化学进展 ›› 2018, Vol. 30 ›› Issue (5) :513-527 DOI: 10.7536/PC171237

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三甲基硅基(TMS)化学:C(sp³)-Si键的催化活化

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作者信息 +

Me₃Si(TMS) Chemistry: Transition-Metal Catalyzed Activation and Utilization of C(sp³)-Si Bond

Qi Yang¹, Kunbing Ouyang^2*, Liang Liu¹, Zhenfeng Xi^1*

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文章历史 +

摘要

三甲基硅基（TMS）广泛存在于有机化合物中，并且在有机合成中有重要的应用。硅杂环化合物因其独特的理化性质而被广泛地应用于有机合成化学、材料化学和药物化学中。因此，将含有TMS基团的化合物直接用于硅杂环化合物合成的研究具有重要的意义。在有机合成化学中，碳硅键的切断是一个非常重要的过程。通过化学计量的有机镁或有机锂等有机金属试剂对C（sp³）—Si键进行切断是碳硅键活化的经典方法，然而该方法的反应条件苛刻，应用有限。过渡金属催化的反应能够在较温和的条件下实现C（sp³）—Si键的切断，这为进一步官能团化C（sp³）—Si键提供了一种新方向，同时也是一种高效构建硅杂环化合物的新方法。目前过渡金属催化活化C（sp³）—Si键的研究主要集中在具有张力环或一些具有特定结构的底物中，对于催化活化惰性C（sp³）—Si键的研究仍然是一个具有挑战性的课题。本文结合本课题组的工作综述了近年来过渡金属催化的TMS中C（sp³）—Si键的方法。

Abstract

The C(sp³)-Si bond in trialkylsilyl groups such as SiMe₃ is among the most frequently encountered C-Si bonds, because many compounds are substituted with trialkylsilyl groups. Silacycles, particularly siloles, have been recognized and extensively studied for their potential applications in organic synthetic chemistry, material science, and medicinal chemistry. The cleavage and applications of the bond is important in organic synthetic chemistry. However, classic methods require a stoichiometric amount of either organo-magnesium or organolithium reagent. The harsh conditions in these methods do not tolerate many functional groups, thus limiting the synthetic application of these approaches. Transition-metal-catalyzed cleavage of the C(sp³)-Si bonds would be ideal for overcoming the limitation. The process not only shows a new and unique entry to functionalize the C(sp³)-Si bond, but also presents a powerful method to synthesize diverse organosilanes. Up to now, the majority of successful examples, in which the strategy of transition metal catalyzed reactions was applied into activation of C(sp³)-Si bonds, has concentrated on the strained cyclic compounds and functionalized substrates. Hence, the activation of unactivated C(sp³)-Si bonds remains a challenging issue. This review article summarizes recent reports on transition-metal-catalyzed cleavage and synthetic applications of the C(sp³)-Si bonds. In addition, the organometallic reagent-promoted cleavage of C(sp³)-Si bonds is also presented for comparison.Contents
1 Introduction
2 Organometallic reagent-promoted cleavage of C(sp³)—Si bonds
3 Transition-metal-catalyzed cleavage and synthetic applications of C(sp³)—Si bonds
3.1 Organosilicon compounds containing strong electron-withdrawing groups
3.2 Strained silacycles
3.3 Inactive C(sp³)—Si bonds
4 Conclusion

Graphical abstract

关键词

三甲基硅基 / C(sp³)-Si键 / 过渡金属催化

Key words

trimethylsilyl group / C(sp³)-Si bond / transition-metal catalysis

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杨琪, 欧阳昆冰, 刘亮, 席振峰. 三甲基硅基(TMS)化学:C(sp³)-Si键的催化活化[J]. 化学进展, 2018, 30(5): 513-527 DOI:10.7536/PC171237

Qi Yang, Kunbing Ouyang, Liang Liu, Zhenfeng Xi. Me₃Si(TMS) Chemistry: Transition-Metal Catalyzed Activation and Utilization of C(sp³)-Si Bond[J]. Progress in Chemistry, 2018, 30(5): 513-527 DOI:10.7536/PC171237

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原文顺序 | 出版日期 | 本文引用

[1] Overman L E, Blumenkopf T A. Chem. Rev., 1986, 86:857.
[2] Panek M, Masse C E. Chem. Rev., 1995, 95:1293.
[3] Langkopf E, Schinzer D. Chem. Rev., 1995, 95:1375.
[4] Fleming I, Barbero A, Walter D. Chem. Rev., 1997, 97:2063.
[5] Lukevics E, Germane S, Segal I, Zablotskaya A. Chem. Heterocycl. Compd., 1997, 33:234.
[6] Sieburth S M N, Nittoli T, Mutahi A M, Guo L X. Angew. Chem. Int. Ed., 1998, 37:812.
[7] Tacke R, Handmann V I, Bertermann R, Burschka C, Penka M, Seyfried C. Organometallics, 2003, 22:916.
[8] Barnes M J, Conroy R, Miller D J, Mills J S, Montana J G, Pooni P K, Showell G A, Walsh L M, Warneck J B H. Bioorg. Med. Chem. Lett., 2007, 17:354.
[9] Chan J C H, Lam H M, Yam V W W. J. Am. Chem. Soc., 2014, 136:16994.
[10] Liu J H, Zhang Q D, Li P, Qu Z, Sun S H, Ma Y P, Su D Y, Zong Y L, Zhang J X. Eur. J. Inorg. Chem., 2014, 3435.
[11] Denmark S E, Sweis R F. Metal-Catalyzed Cross-Coupling Reactions. 2 nd ed. Weinheim:Wiley-VCH, 2004. 163.
[12] Jones G R, Landais Y. Tetrahedron, 1996, 52:7599.
[13] Franz A K, Woerpel K A. Acc. Chem. Res., 2000, 33:813.
[14] Rauf W, Hazari A, Gouverneur V, Brown J M. Pure Appl. Chem., 2010, 82:1415.
[15] Hiyama T. J. Syn. Org. Chem. Jpn., 2010, 68:729.
[16] Cheng C, Hartwig J F. Chem. Rev., 2015, 115:8946.
[17] Hatanaka Y, Hiyama T. J. Org. Chem., 1988, 53:918.
[18] Sonogashira K. J. Organomet. Chem., 2002, 653:46.
[19] Boxer M B, Yamamoto H. J. Am. Chem. Soc., 2006, 128:48.
[20] van Klink G P M, de Boer H J R, Schat G, Akkerman O S, Bickelhaupt F, Spek A L. Organometallics, 2002, 21:2119.
[21] Hudrlik P F, Dai D H, Hudrlik A M. J. Organomet. Chem., 2006, 691:1257.
[22] Xi Z F. Bull. Chem. Soc. Jpn., 2007, 80:1021.
[23] Wang C, Luo Q, Sun H, Guo X Y, Xi Z F. J. Am. Chem. Soc., 2007, 129:3094.
[24] Wang L L, Duan Z. Chin. Sci. Bull., 2013, 58:307.
[25] Zhang Q, An K, He W. Synlett, 2015, 26:1145.
[26] Li L J, Zhang Y B, Gao L, Song Z. Tetrahedron Lett., 2015, 56:1466.
[27] Komiyama T, Minami Y, Hiyama T. ACS Catal., 2017, 7:631.
[28] Hiyama T. In Metal-Catalyzed Cross-Coupling Reactions. Weinheim:Wiley-VCH, 1998.
[29] Hiyama T. J. Organomet. Chem., 2002, 653:58.
[30] Denmark S E, Sweiss R F. Acc. Chem. Res., 2002, 35:835.
[31] Spivey A C, Gripton C J G, Hannah J P. Curr. Org. Synth., 2004, 1:211.
[32] Denmark S E, Baird J D. Chem. Eur. J., 2006, 12:4954.
[33] Nakao Y, Imanaka H, Sahoo A K, Yada A, Hiyama T. J. Am. Chem. Soc., 2005, 127:6952.
[34] Alacid E, Nájera C. Adv. Synth. Catal., 2006, 348:2085.
[35] Yang S B, Li B J, Wan X B, Shi Z J. J. Am. Chem. Soc., 2007, 129:6066.
[36] Dai X, Strotman N A, Fu G C. J. Am. Chem. Soc., 2008, 130:3302.
[37] Zhang L, Wu J. J. Am. Chem. Soc., 2008, 130:12250.
[38] Luo Q, Wang C, Li Y, Ouyang K B, Gu L, Uchiyama M, Xi Z. Chem. Sci., 2011, 2:2271.
[39] Zhang W X, Zhang S G, Xi Z F. Acc. Chem. Res., 2011, 44:541.
[40] Zhang S, Zhang W X, Zhao J, Xi Z F. J. Am. Chem. Soc., 2010, 132:14042.
[41] Wu M J, Wei L M, Lin C F, Leou S P, Wei L L. Tetrahedron, 2001, 57:7839.
[42] Sommer W J, Weck M. Adv. Synth. Catal., 2006, 348:2101.
[43] Horita A, Tsurugi H, Satoh T, Miura M. Org. Lett., 2008, 10:1751.
[44] Huang H, Liu H, Jiang H L, Chen K X. J. Org. Chem., 2008, 73:6037.
[45] Sakai N, Komatsu R, Uchida N, Ikeda R, Konakahara T. Org. Lett., 2010, 12:1300.
[46] Wang Z H, Fang H Y, Xi Z F. Tetrahedron Lett., 2005, 46:499.
[47] Yu N, Wang C Y, Zhao F, Liu L T, Zhang W X, Xi Z F. Chem. Eur. J., 2008, 14:5670.
[48] Wang C, Luo Q, Sun H, Guo X Y, Xi Z F. J. Am. Chem. Soc., 2007, 129:3094.
[49] Hosomi A. Acc. Chem. Res., 1988, 21:200.
[50] Fleming I, Barbero A, Walter D. Chem. Rev., 1997, 97:2063.
[51] Matsuda T, Kadowaki S, Yamaguchi Y, Murakami M. Chem. Commun., 2008, 2744.
[52] Kolomeitsev A, Rusanov E, Bissky G, Lork E, Röschenthaler G V, Kirsch P. Chem. Commun., 1999, 1017.
[53] Liu X, Xu C, Wang M, Liu Q. Chem. Rev., 2015, 115:683.
[54] Franz A K, Woerpel K A. Acc. Chem. Res., 2000, 33:813.
[55] Hirano K, Yorimitsu H, Oshima K. Chem. Commun., 2008, 3234.
[56] Seiser T, Cramer N. Angew. Chem., Int. Ed., 2010, 49:10163.
[57] Matsuda T, Suda Y, Fujisaki Y. Synlett, 2011, 813.
[58] Cramer N, Seiser T. Synlett, 2011, 449.
[59] Ishida N, Ikemoto W, Murakami M. J. Am. Chem. Soc., 2014, 136:5912.
[60] 罗渝然(Luo Y R). 化学键能数据手册(The Handbook of Chemical Bond Energy). 北京:科学出版社(Beijing:Science Press), 2005.
[61] Tamao K. Proc. Jpn. Acad. Ser. B, 2008, 84:123.
[62] Prakash G K S, Krishnamurt R, Olah G A. J. Am. Chem. Soc., 1989, 111:393.
[63] Yamaguchi S K, Tamao K. Silicon Containing Polymers:The Science and Technology of Their Synthesis and Applications. Dordrecht:Kluwer Academic Publishers, 2000. 498.
[64] Yamaguchi S, Tamao K. J. Organomet. Chem., 2002, 653:223.
[65] Hissler M, Dyer P W, Réau R. Coord. Chem. Rev., 2003, 244:1.
[66] Yamaguchi S, Xu C, Okamoto T. Pure Appl. Chem., 2006, 78:721.
[67] Chen J J, Cao Y. Macromol.Rapid Commun., 2007, 28:1714.
[68] 刘俊辉(Liu J), 张文雄(Zhang W X), 席振峰(Xi Z F). 有机化学(Chinese Journal of Organic Chemistry), 2009, 29:491.
[69] (a)张韶光(Zhang S G), 刘俊辉(Liu J H), 张文雄(Zhang W X), 席振峰(Xi Z F). 化学进展(Progress in Chemistry), 2009, 12:1487.;
(b)刘俊辉(Liu J H), 张韶光(Zhang S G), 张文雄(Zhang W X), 席振峰(Xi Z F). 化学进展(Progress in Chemistry), 2009, 12:1475.
[70] Liu J H, Sun X H, Miyazaki M, Liu L T, Wang C Y, Xi Z F. J. Org. Chem., 2007, 72:3137.
[71] Matsumoto K, Oshima K, Utimoto K. J. Syn. Org. Chem. Jpn., 1996, 54:289.
[72] Tanaka Y, Yamashita H,Shimada S,Tanaka M. Organometallics, 1997, 16:3246.
[73] Li L W, Zhang Y B, Gao L, Song Z L. Tetrahedron Lett., 2015, 56:1466.
[74] Zhang Q W, An K, Liu L G, Zhang Q, Guo H F, He W. Angew. Chem. Int. Ed., 2017, 56:1125.
[75] Cheng C, Hartwig J F. J. Am. Chem. Soc., 2014, 136:12064.
[76] Rauf W, Brown M. Angew. Chem. Int. Ed., 2008, 47:4228.
[77] Nakao Y, Takeda M, Matsumoto T, Hiyama T. Angew. Chem. Int. Ed., 2010, 49:4447.
[78] Liang Y, Zhang S G, Xi Z F. J. Am. Chem. Soc., 2011, 133:9204.
[79] Zask A, Helquist P. J. Org. Chem., 1978, 43:1619.
[80] Viciu M S, Grasa G A, Nolan S P. Organometallics, 2001, 20:3607.
[81] Navarro O, Kaur H, Mahjoor P, Nolan S P. J. Org. Chem., 2004, 69:3173.
[82] Alonso F, Beletskaya I P, Yus M. Chem. Rev., 2002, 102:4009.
[83] Moon J J, Lee S W. J. Organomet. Chem., 2009, 694:473.
[84] Liang Y, Geng W J, Wei J N, Xi Z F. Angew. Chem. Int. Ed., 2012, 51:1934.
[85] Chen W T, Lin Z Y. Dalton Trans., 2014, 43:11138.
[86] Tadross P M, Stoltz B M. Chem. Rev., 2012, 112:3550.
[87] Bhunia A, Yetra S R, Biju A T. Chem. Soc. Rev., 2012, 41:3140.
[88] Parthasarathy K, Han H, Prakash C, Cheng C H. Chem. Commun., 2012, 48:6580.
[89] Meng T H, Ouyang K B, Xi Z F. RSC Adv., 2013, 3:14273.
[90] Tobisu M, Onoe M, Kita Y, Chatani N. J. Am.Chem. Soc., 2009, 131:7506.
[91] Onoe M, Baba K, Kim Y, Kita Y, Tobisu M, Chatani N. J. Am. Chem. Soc., 2012, 134:19477.
[92] Zhang Q W, An K, He W. Angew. Chem. Int. Ed., 2014, 53:5667.
[93] Yu Z Y, Lan Y. J. Org. Chem., 2013, 78:11501.
[94] Yang Q, Liu L, Chi Y, Hao W, Zhang W X, Xi Z F. Org. Chem. Front., 2017, 5:860.
[95] 欧阳昆冰(Ouyang K B), 席振峰(Xi Z F). 化学学报(Acta Chimica Sinica), 2013, 71:13.
[96] 杨琪(Yang Q), 刘亮(Liu L), 张文雄(Zhang W X), 席振峰(Xi Z F). 有机化学(Chinese Journal of Organic Chemistry), 2018, 38:272.
[97] Olah G A, Meyer W, Overchuk N A. J. Org. Chem., 1964, 29:2313.
[98] Olah G A, Meyer W, Overchuk N A. J. Org. Chem., 1964, 29:2315.
[99] Dudnik A S, Xia Y Z, Li Y H, Gevorgyan V. J. Am. Chem. Soc., 2010, 132:764.
[100] Chen M, Sun N, Xu W, Zhao J D, Wang G N, Liu Y H. Chem. Eur. J., 2015, 21:18571.
[101] Yu M M, Fu X F. J. Am. Chem. Soc., 2011, 133:15926.