SIOC English
有机化学
高级检索

有机化学 >

2020 , Vol. 40 >Issue 10: 3132 - 3153

DOI: https://doi.org/10.6023/cjoc202005092

综述与进展

1,3-偶极子[3+n](n≥3)环加成反应的研究进展

  • 乐贵洲 ,
  • 刘波
展开
  • a 四川农业大学理学院 四川雅安 625014;
    b 四川大学化学学院 绿色化学与技术教育部重点实验室 成都 610064

收稿日期: 2020-05-30

  修回日期: 2020-06-19

  网络出版日期: 2020-07-01

基金资助

四川省科技计划（No.2020YFH0129）资助项目.

收起

Research Progress on [3+n] (n≥3) Cycloaddition of 1,3-Diploes

  • Yue Guizhou ,
  • Liu Bo
Expand
  • a School of Science, Sichuan Agricultural University, Ya'an, Sichuan 625014;
    b Key Laboratory of Green Chemistry & Technology of Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064

Received date: 2020-05-30

  Revised date: 2020-06-19

  Online published: 2020-07-01

Supported by

Project supported by the Science and Technology Program of Sichuan Province (No. 2020YFH0129).

Fold

摘要

各种杂环骨架广泛存在于天然产物、药物分子及有机材料中，它们的合成方法也多种多样，其中1，3-偶极环加成反应是构建杂环重要的一类方法.2005年之前，有机化学家们将精力主要集中在1，3-偶极子的[3+2]环加成反应，构建五元杂环；随着研究的深入，逐渐将注意力转向[3+3]、[3+4]、[3+5]及[3+6]等环加成，构建六元、七元、八元及桥杂环等.关于1，3-偶极环加成反应的综述已有很多，但它们讨论的重点是[3+2]环加成.到目前为止，还没有专门的综述来探讨其它环加成反应的概况及其应用前景.因此，对各种1，3-偶极子的[3+n]（n≥3）环加成反应进行详细的综述及评论，并对其领域提出展望.

关键词： 1,3-偶极环加成; 硝酮; 亚甲胺叶立德; 偶氮次甲基亚胺; 氰基亚胺; 氰基氧化物; 氰基叶立德

本文引用格式

乐贵洲 , 刘波 . 1,3-偶极子[3+n](n≥3)环加成反应的研究进展[J]. 有机化学, 2020 , 40(10) : 3132 -3153 . DOI: 10.6023/cjoc202005092

Abstract

Versatile heterocyclic skeletons extensively exist in structures of natural products, drug molecules and organic materials, and have been synthesized through various strategies reported in literatures. Among them, the 1,3-dipolar cycloaddition is the most impressive class to build the related heterocycles. In the past, organic chemists generally employed[3+2] cycloaddition of 1,3-dipoles to assemble five-membered rings. As modern chemistry developes, researchers further turn their attention to the[3+3],[3+4],[3+5] and[3+6] cycloadditions, to construct six-, seven-, eight- and bridge-heterocyclic compounds. At present, review articles with topics on 1,3-dipolar cycloaddition mainly focus on[3+2] cycloaddition. Herein, A topic on[3+n] (n ≥ 3) cycloaddition of 1,3-dipoles, with comments on the developed methodologies is present and the outlook in this field is proposed.

Key words： 1,3-diploar cycloaddtion; nitrone; azomethine ylide; azomethine imine; nitrile imine; nitrile oxide; nitrile ylide

参考文献

[1] Seeman, J. I.; Restrepo, G. Angew. Chem. Int. Ed. 2020, 59, 12250.
[2] Huisgen, P. D. R. Angew. Chem. Int. Ed. 1963, 2, 565.
[3] Delpierre, G.; Lamchen, M. Quart. Rev. Chem. Soc. 1965, 19, 329.
[4] Stuckwisch, C. G. Synthesis 1973, 469.
[5] Timpe, H.-J. Heteroaromatic N-Imines. In Advances in Heterocyclic Chemistry, Eds:Katritzky, A. R.; Boulton, A. J., Academic Press, Pittsburgh, 1974; Vol. 17, p. 213.
[6] Black, D. S. C.; Crozier, R. F.; Davis, V. C. Synthesis 1975, 205.
[7] Tamura, Y.; Ikeda, M. Advances in the Chemistry of Heteroaromatic N-Imines and N-Aminoazonium Salts. In Advances in Heterocyclic Chemistry, Eds.:Katritzky, A. R.; Boulton, A. J., Academic Press, Pittsburgh, 1981; Vol. 29, p. 71.
[8] Gothelf, K. V.; Jørgensen, K. A. Chem. Rev. 1998, 98, 863.
[9] Rodina, L. L.; Kolberg, A.; Schulze, B. Heterocycles 1998, 49, 587.
[10] Zhao B.-X. Prog. Chem. 2000, 12, 77(in Chinese). (赵宝祥, 化学进展, 2000, 12, 77.)
[11] Xu J.-X.; Jiao P. Prog. Chem. 2000, 12, 131(in Chinese). (许家喜, 焦鹏, 化学进展, 2000, 12, 131.)
[12] Kolb, H. C.; Finn, M. G.; Sharpless, K. B. Angew. Chem. Int. Ed. 2001, 40, 2004.
[13] Kotyatkina, A. I.; Zhabinsky, V N.; Khripach, V. A. Russ. Chem. Rev. 2001, 70, 641.
[14] Osborn, H. M. I.; Gemmell, N.; Harwood, L. M. J. Chem. Soc., Perkin Trans. 12002, 2419.
[15] Padwa A.; Pearson W. H. The Chemistry of Heterocyclic Compounds:Synthetic Applications of 1,3-Dipolar Cycloaddition Chemistry Toward Heterocycles and Natural Products, Vol. 59, John Wiley & Sons, New York, 2002.
[16] Schantl, J. G. Sci. Synth. 2004, 27, 731.
[17] Harju, K.; Yli-Kauhaluoma, J. Mol. Div. 2005, 9, 187.
[18] Rück-Braun, K.; Freysoldt, T. H. E.; Wierschem, F. Chem. Soc. Rev. 2005, 34, 507.
[19] Coldham, I.; Hufton, R. Chem. Rev. 2005, 105, 2765.
[20] Hu, X.-F.; Feng, Y.-Q.; Li, X.-F. Chin. J. Org. Chem. 2005, 25, 1(in Chinese). (胡晓芬, 冯亚青, 李筱芳, 有机化学, 2005, 25, 1.)
[21] Pinho e Melo, T. M. V. D. Eur. J. Org. Chem. 2006, 2006, 2873.
[22] Pandey, G.; Banerjee, P.; Gadre, S. R. Chem. Rev. 2006, 106, 4484.
[23] Wang, F.; Bai D.-L. Chin. J. Org. Chem. 2006, 26, 9(in Chinese). (王峰, 白东鲁, 有机化学, 2006, 26, 9.)
[24] Moses, J. E.; Moorhouse, A. D. Chem. Soc. Rev. 2007, 36, 1249.
[25] Nair, V.; Suja, T. D. Tetrahedron 2007, 63, 12247.
[26] Stanley, L. M.; Sibi, M. P. Chem. Rev. 2008, 108, 2887.
[27] Jewett, J. C.; Bertozzi, C. R. Chem. Soc. Rev. 2010, 39, 1272.
[28] Adrio, J.; Carretero, J. C. Chem. Commun. 2011, 47, 6784.
[29] Yang, J. Synlett 2012, 2293.
[30] Lashgari, N.; Ziarani, G. M. ARKIVOC 2012, i, 277.
[31] Tanimoto, H.; Kakiuchi, K. Nat. Prod. Commun. 2013, 8, 1021.
[32] Xu, X.; Doyle, M. P. Acc. Chem. Res. 2014, 47, 1396.
[33] Han, Q.; Yi, C.; Xiong, X., Chin. J. Org. Chem. 2014, 34, 1092(in Chinese). (韩骞, 易超; 熊兴泉, 有机化学, 2014, 34, 1092.)
[34] Hashimoto, T.; Maruoka, K. Chem. Rev. 2015, 115, 5366.
[35] Najera, C.; Sansano, J. M.; Yus, M. Org. Biomol. Chem. 2015, 13, 8596.
[36] Padwa, A.; Bur, S. Recent Advances of 1,3-Dipolar Cycloaddition Chemistry for Alkaloid Synthesis. In Advances in Heterocyclic Chemistry, Eds.:Scriven, E. F. V.; Ramsden C. A., Academic Press, Pittsburgh, 2016, Vol. 119, p. 241.
[37] Sears, J. E.; Boger, D. L. Acc. Chem. Res. 2016, 49, 241.
[38] Meyer, A. G.; Ryan, J. H. Molecules 2016, 21, 935.
[39] Belskaya, N. P.; Bakulev, V. A.; Fan, Z. Chem. Heterocycl. Compd. 2016, 52, 627.
[40] Yuan, B.-B.; Li, Y.-M.; Wang, Q.-L.; Bu, Z.-W. Chem. Res. 2017, 28, 135(in Chinese). (袁贝贝, 李雅宁, 郭娇美, 王琪琳, 卜站伟, 化学研究, 2017, 28, 135.)
[41] Pozgan, F.; Al Mamari, H.; Groselj, U.; Svete, J.; Stefane, B. Molecules 2017, 23, 3.
[42] Xuan, J.; Cao, X.; Cheng, X. Chem. Commun. 2018, 54, 5154.
[43] Li, J.; Ye, Y.; Zhang, Y. Org. Chem. Front. 2018, 5, 864.
[44] Arrastia, I.; Arrieta, A.; Cossío, F. P. Eur. J. Org. Chem. 2018, 5889.
[45] Grošelj, U.; Svete, J.; Mamari, H. H. A.; Požgan, F.; Štefane, B. Chem. Heterocycl. Compd. 2018, 54, 214.
[46] Grošelj, U.; Požgan, F.; Štefane, B.; Svete, J. Synthesis 2018, 4501.
[47] Frankowski, S.; Romaniszyn, M.; Skrzynska, A.; Albrecht, L. Chemistry 2019.
[48] Gulevskaya, A. V.; Nelina-Nemtseva, J. I. Chem. Heterocycl. Compd. 2019, 54, 1084.
[49] Gao, K.; Zhang, Y. G.; Wang, Z.; Ding, H. Chem. Commun. 2019, 55, 1859.
[50] Sukhorukov, A. Adv. Synth. Catal. 2019, 362, 724.
[51] Nebra, N.; García-Álvarez, J. Molecules 2020, 25, 2015.
[52] Zhu, Y.; Huang, Y. Synthesis 2020, 1181.
[53] Brunel, D.; Dumur, F. New J. Chem. 2020, 44, 3546.
[54] Gui, H.-Z.; Wei, Y.; Shi, M. Chem. Asian J. 2020, 15, 1225.
[55] Dhameja, M.; Kumar, H.; Gupta, P. Asian J. Org. Chem. 2020, in press.
[56] Breugest, M.; Reissig, H. U. Angew. Chem. Int. Ed. 2020, 59, 12293.
[57] Wei, L.; Chang, X.; Wang, C.-J. Acc. Chem. Res. 2020, 53, 1084.
[58] Mori, M.; Sugiyama, T.; Nojima, M.; Kusabayashi, S.; Mc- Cullough, K. J. J. Org. Chem. 1992, 57, 2285.
[59] Schneider, T. F.; Kaschel, J.; Werz, D. B. Angew. Chem. Int. Ed. 2014, 53, 5504.
[60] Singh, P.; Varshnaya, R. K.; Dey, R.; Banerjee, P. Adv. Syn. Catal. 2020, 362, 1447.
[61] Werz, D. B.; Biju, A. T. Angew. Chem. Int. Ed. 2020, 59, 3385.
[62] Ivanova, O. A.; Trushkov, I. V. Chem. Rec. 2020, 19, 2189.
[63] Wu, L.; Shi, M. Chem. Eur. J. 2010, 16, 1149.
[64] Yang, W.; Wang, T.; Yu, Y.; Shi, S.; Zhang, T.; Hashmi, A. S. K. Adv. Syn. Catal. 2013, 355, 1523.
[65] El Bouakher, A.; Martel, A.; Comesse, S. Org. Biomol. Chem. 2019, 17, 8467.
[66] An, Y.; Xia, H.; Wu, J. Chem. Commun. 2016, 52, 10415.
[67] Zhao, H.-W.; Zhao, Y.-D.; Liu, Y.-Y.; Zhao, L.-J.; Song, X.-Q.; Chen, X.-Q.; Pang, H.-L.; Du, J.; Feng, N.-N. RSC Adv. 2017, 7, 55106.
[68] Jia, Q.; Li, D.; Lang, M.; Zhang, K.; Wang, J. Adv. Syn. Catal. 2017, 359, 3837.
[69] Luo, Y.; Chen, C.-H.; Zhang, J.-Q.; Liang, C.; Mo, D.-L. Synthesis 2019, 52, 424.
[70] Sibi, M. P.; Ma, Z.; Jasperse, C. P. J. Am. Chem. Soc. 2005, 127, 5764.
[71] Sapeta, K.; Kerr, M. A. J. Org. Chem. 2007, 72, 8597.
[72] Wang, X.; Xu, X.; Zavalij, P. Y.; Doyle, M. P. J. Am. Chem. Soc. 2011, 133, 16402.
[73] Xu, X.; Zavalij, P. J.; Doyle, M. P. Chem. Commun. 2013, 49, 10287.
[74] Shintani, R.; Park, S.; Duan, W. L.; Hayashi, T. Angew. Chem. Int. Ed. 2007, 46, 5901.
[75] Liu, F.; Qian, D.; Li, L.; Zhao, X.; Zhang, J. Angew. Chem. Int. Ed. 2010, 49, 6669.
[76] Zhou, L.; Xu, B.; Ji, D.; Zhang, Z. M.; Zhang, J. Chin. J. Chem. 2020, in press.
[77] Xu, P. W.; Liu, J. K.; Shen, L.; Cao, Z. Y.; Zhao, X. L.; Yan, J.; Zhou, J. Nat. Commun. 2017, 8, 1619.
[78] Bai, Y.; Fang, J.; Ren, J.; Wang, Z. Chem. Eur. J. 2009, 15, 8975.
[79] Stevens, A. C.; Palmer, C.; Pagenkopf, B. L. Org. Lett. 2011, 13, 1528.
[80] Zhang, Y.; Zhang, J. Chem. Commun. 2012, 48, 4710.
[81] Hu, J.-L.; Wang, L.; Xu, H.; Xie, Z.; Tang, Y. Org. Lett. 2015, 17, 2680.
[82] Shintani, R.; Murakami, M.; Hayashi, T. J. Am. Chem. Soc. 2007, 129, 12356.
[83] Shintani, R.; Murakami, M.; Hayashi, T. Pure Appl. Chem. 2008, 80, 1135.
[84] Gawade, S. A.; Bhunia, S.; Liu, R. S. Angew. Chem. Int. Ed. 2012, 51, 7835.
[85] Shintani, R.; Hayashi, T. J. Am. Chem. Soc. 2006, 128, 6330.
[86] Li, S.-N.; Yu, B.; Liu, J.; Li, H.-L.; Na, R. Synlett 2016, 27, 282.
[87] Wang, K.-K.; Li, Y.-L.; Wang, Z.-Y.; Hu, M.-W.; Qiu, T.-T.; Zhu, B.-K. Org. Biomol. Chem. 2018, 17, 244.
[88] Perreault, C.; Goudreau, S. R.; Zimmer, L. E.; Charette, A. B. Org. Lett. 2008, 10, 689.
[89] Chagarovskiy, A. O.; Vasin, V. S.; Kuznetsov, V. V.; Ivanova, O. A.; Rybakov, V. B.; Shumsky, A. N.; Makhova, N. N.; Trushkov, I. V. Angew. Chem. Int. Ed. 2018, 57, 10338.
[90] Chagarovskiy, A. O.; Kuznetsov, V. V.; Ivanova, O. A.; Goloveshkin, A. S.; Levina, I. I.; Makhova, N. N.; Trushkov, I. V. Eur. J. Org. Chem. 2019, 2019, 5475.
[91] Na, R.; Jing, C.; Xu, Q.; Jiang, H.; Wu, X.; Shi, J.; Zhong, J.; Wang, M.; Benitez, D.; Tkatchouk, E.; Goddard, W. A.; Guo, H.; Kwon, O. J. Am. Chem. Soc. 2011, 133, 13337.
[92] Liang, L.; Huang, Y. Org. Lett. 2016, 18, 2604.
[93] Li, Y.; Zhang, Z. New J. Chem. 2019, 43, 13600.
[94] Liu, J.; Liu, H.; Na, R.; Wang, G.; Li, Z.; Yu, H.; Wang, M.; Zhong, J.; Guo, H. Chem. Lett. 2012, 41, 218.
[95] Li, Z.; Yu, H.; Liu, Y.; Zhou, L.; Sun, Z.; Guo, H. Adv. Synth. Catal. 2016, 358, 1880.
[96] Qian, Y.; Zavalij, P. J.; Hu, W.; Doyle, M. P. Org. Lett. 2013, 15, 1564.
[97] Cheng, X.; Cao, X.; Xuan, J.; Xiao, W.-J. Org. Lett. 2018, 20, 52.
[98] Ansari, A. J.; Pathare, R. S.; Kumawat, A.; Maurya, A. K.; Verma, S.; Agnihotri, V. K.; Joshi, R.; Metre, R. K.; Sharon, A.; Pardasani, R. T.; Sawant, D. M. New J. Chem. 2019, 43, 13721.
[99] Zhu, G.; Sun, W.; Wu, C.; Li, G.; Hong, L.; Wang, R. Org. Lett. 2013, 15, 4988.
[100] Fang, X.; Li, J.; Tao, H.-Y.; Wang, C.-J. Org. Lett. 2013, 15, 5554.
[101] Du, J.; Xu, X.; Li, Y.; Pan, L.; Liu, Q. Org. Lett. 2014, 16, 4004.
[102] Shapiro, N. D.; Shi, Y.; Toste, F. D. J. Am. Chem. Soc. 2009, 131, 11654.
[103] Chan, A.; Scheidt, K. A. J. Am. Chem. Soc. 2007, 129, 5334.
[104] Efremova, M. M.; Kostikov, R. R.; Stepakov, A. V.; Panikorovsky, T. L.; Shcherbakova, V. S.; Ivanov, A. V.; Molchanov, A. P. Tetrahedron 2017, 73, 671.
[105] T. P.; Krishna, A. V.; Ramachary, D. B. Org. Lett. 2018, 20, 6979.
[106] Fang, Q-Y.; Jin, H-S.; Wang, R-B.; Zhao, L-M. Chem. Commun. 2019, 55, 10587.
[107] Liu, Y.; Zhen, W.; Dai, W.; Wang, F.; Li, X. Org. Lett. 2013, 15, 874.
[108] Moghaddam, F. M.; Eslami, M.; Siahpoosh, A.; Golfam, H. New J. Chem. 2019, 42, 10318.
[109] Wang, X.; Yang, P.; Zhang, Y.; Tang, C.-Z.; Tian, F.; Peng, L.; Wang, L.-X. Org. Lett. 2017, 19, 646.
[110] Hu, S.; Zhang, J.; Jin, Q. New J. Chem. 2018, 42, 7025.
[111] Zhou, Y. Y.; Li, J.; Ling, L.; Liao, S. H.; Sun, X. L.; Li, Y. X.; Wang, L. J.; Tang, Y. Angew. Chem. Int. Ed. 2013, 52, 1452.
[112] Guo, H.; Liu, H.; Zhu, F.-L.; Na, R.; Jiang, H.; Wu, Y.; Zhang, L.; Li, Z.; Yu, H.; Wang, B.; Xiao, Y.; Hu, X.-P.; Wang, M. Angew. Chem. Int. Ed. 2013, 52, 12641.
[113] Zhang, L.; Liu, H.; Qiao, G.; Hou, Z.; Liu, Y.; Xiao, Y.; Guo, H. J. Am. Chem. Soc. 2015, 137, 4316.
[114] Du, Q.; Neudoerfl, J.-M.; Schmalz, H.-G. Chem. Eur. J. 2018, 24, 2379.
[115] Xu, X.; Xu, X.; Zavalij, P. Y.; Doyle, M. P. Chem. Commun. 2013, 49, 2762.
[116] Jing, C.; Na, R.; Wang, B.; Liu, H.; Zhang, L.; Liu, J.; Wang, M.; Zhong, J.; Kwon, O.; Guo, H. Adv. Synth. Catal. 2012, 354, 1023.
[117] Li, Z.; Yu, H.; Feng, Y.; Hou, Z.; Zhang, L.; Yang, W.; Wu, Y.; Xiao, Y.; Guo, H. RSC Adv. 2015, 5, 34481.
[118] Hu, X.-Q.; Chen, J.-R.; Gao, S.; Feng, B.; Lu, L.-Q.; Xiao, W.-J. Chem. Commun. 2013, 49, 7905.
[119] Li, Z.; Li, S.; Kan, T.; Wang, X.; Xin, X.; Hou, Y.; Gong, P. Adv. Synth. Catal. 2020, 362, 2626.
[120] Water, R. W. V. D.; Pettus, T. R. R. Tetrahedron 2002, 58, 5367.
[121] Grotenhuis, C. T.; Bruin, B. D. Synlett 2018, 29, 2238.
[122] Yang, B.; Gao, S. Chem. Soc. Rev. 2018, 47, 7926.
[123] Mei, G.-J.; Zhu, Z.-Q.; Zhao, J.-J.; Bian, C.-Y.; Chen, J.; Chen, R.-W.; Shi, F. Chem. Commun. 2017, 53, 2768.
[124] Chen, L.; Yang, G.; Wang, J.; Jia, Q.; Wei, J.; Du, Z. RSC Adv. 2015, 5, 76696.
[125] Jin, Q.; Zhang, J.; Jiang, C.; Zhang, D.; Gao, M.; Hu, S. J. Org. Chem. 2018, 83, 8410.
[126] Li, C.; Wang, C. S.; Li, T. Z.; Mei, G. J.; Shi, F. Org. Lett. 2019, 21, 598.
[127] Dai, W.; Li, C.; Liu, Y.; Han, X.; Li, X.; Chen, K.; Liu, H. Org. Chem. Front. 2020, 7, 2612..
[128] Wei, L.; Wang, Z. F.; Yao, L.; Qiu, G.; Tao, H.; Li, H.; Wang, C. J. Adv. Syn. Catal. 2016, 358, 3955.
[129] Yuan, C.; Wu, Y.; Wang, D.; Zhang, Z.; Wang, C.; Zhou, L.; Zhang, C.; Song, B.; Guo, H. Adv. Syn. Catal. 2018, 360, 652.
[130] Yang, Q.-Q.; Yin, X.; He, X.-L.; Du, W.; Chen, Y.-C. ACS Catal. 2019, 9, 1258.
[131] Wu, Y.; Qiao, G.; Liu, H.; Zhang, L.; Sun, Z.; Xiao, Y.; Guo, H. RSC Adv. 2015, 5, 84290.
[132] Shi, F.; Zhu, R. Y.; Dai, W.; Wang, C. S.; Tu, S. J. Chem.-Eur. J. 2014, 20, 2597.
[133] Yuan, C.; Liu, H.; Gao, Z.; Zhou, L.; Feng, Y.; Xiao, Y.; Guo, H., Org. Lett. 2015, 17, 26.
[134] Yang, W.-L.; Li, C.-Y.; Qin, W.-J.; Tang, F.-F.; Yu, X.; Deng, W.-P. ACS Catal. 2016, 6, 5685.
[135] Kim, S.; Kim, S.-G. Asian J. Org. Chem. 2019, 8, 1621.
[136] Dai, Z.; Zhu, J.; Wang, J.; Su, W.; Yang, F.; Zhou, Q. Adv. Synth. Catal. 2019, 362, 545.
[137] Zhao, H.-W.; Wang, L.-R.; Guo, J.-M.; Ding, W.-Q.; Song, X.-Q.; Wu, H.-H.; Tang, Z.; Fan, X.-Z.; Bi, X.-F. Adv. Synth. Catal. 2019, 361, 4761.
[138] Niu, B.; Wu, X. Y.; Wei, Y.; Shi, M. Org. Lett. 2019, 21, 4859.
[139] Wu, Y.; Liu, H.; Zhang, L.; Sun, Z.; Xiao, Y.; Huang, J.; Wang, M.; Guo, H. RSC Adv. 2016, 6, 73547.
[140] Potowski, M.; Bauer, J. O.; Strohmann, C.; Antonchick, A. P.; Waldmann, H. Angew. Chem. Int. Ed. 2012, 51, 9512.
[141] He, Z.-L.; Teng, H.-L.; Wang, C.-J. Angew. Chem. Int. Ed. 2013, 52, 2934.
[142] Teng, H. L.; Yao, L.; Wang, C. J. J. Am. Chem. Soc. 2014, 136, 4075.
[143] Li, Q. H.; Wei, L.; Wang, C. J. J. Am. Chem. Soc. 2014, 136, 8685.
[144] He, Z. L.; Sheong, F. K.; Li, Q. H.; Lin, Z.; Wang, C. J. Org. Lett. 2015, 17, 1365.
[145] Liu, H.; Wu, Y.; Zhao, Y.; Li, Z.; Zhang, L.; Yang, W.; Jiang, H.; Jing, C.; Yu, H.; Wang, B.; Xiao, Y.; Guo, H. J. Am. Chem. Soc. 2014, 136, 2625.
[146] Petzold, M.; Jones, P. G.; Werz, D. B. Angew. Chem. Int. Ed. 2019, 58, 6225.
[147] Petzold, M.; Günther, A.; Jones, P. G., Werz, D. B. Chem.-Eur. J. 2020, in press.
[148] Suneja, A.; Loui, H. J.; Schneider, C. Angew. Chem. Int. Ed. 2020, 59, 5536.
[149] McLeod, D.; Cherubini-Celli, A.; Sivasothirajah, N.; McCulley, C. H.; Christensen, M. L.; Jørgensen, K. A. Chem.-Eur. J. 2020, 26, 11417.
[150] Garve, L. K.; Petzold, M.; Jones, P. G.; Werz, D. B. Org. Lett. 2016, 18, 564.
[151] Zhao, H.-W.; Zhao, Y.-D.; Liu, Y.-Y.; Zhao, L.-J.; Song, X.-Q.; Chen, X.-Q.; Pang, H.-L.; Du, J.; Feng, N.-N. RSC Adv. 2017, 7, 55106.
[152] Pearson, W. H.; Fang, W.; Kampf, J. W. J. Org. Chem. 1994, 59, 2682.
[153] Scadeng, O.; Ferguson, M. J.; West, F. G. Org. Lett. 2011, 13, 114.
[154] Zhang, H.-H.; Luo, Y.-C.; Wang, H.-P.; Chen, W.; Xu, P.-F. Org. Lett. 2014, 16, 4896.
[155] Xu, X.; Zhang, K.; Li, P.; Yao, H.; Lin, A. Org. Lett. 2018, 20, 1781.
[156] D'Souza, A. M.; Spiccia, N.; Basutto, J.; Jokisz, P.; Wong, L. S.-M.; Meyer, A. G.; Holmes, A. B.; White, J. M.; Ryan, J. H. Org. Lett. 2011, 13, 486.
[157] D'Souza, A. M.; Rivinoja, D. J.; Mulder, R. J.; White, J. M.; Meyer, A. G.; Hyland, C. J. T.; Ryan, J. H. Aust. J. Chem. 2018, 71, 690.
[158] Soeta, T.; Tamura, K.; Ukaji, Y. Org. Lett. 2012, 14, 1226.
[159] Wu, Y.; Tian, B.; Hu, C.; Sekine, K.; Rudolph, M.; Rominger, F.; Hashmi, S. Org. Biomol. Chem. 2019, 17, 5505.
[160] Kumari, P.; Liu, W.; Wang, C. J.; Dai, J.; Wang, M. X.; Yang, Q. Q.; Deng, Y. H.; Shao, Z. Chin. J. Chem. 2019, 38, 151.
[161] Trost, B. M.; Zuo, Z. Angew. Chem. Int. Ed. 2020, 59, 1243.
[162] Zheng, P.; Li, C.; Mou, C.; Pan, D.; Wu, S.; Xue, W.; Jin, Z.; Chi, Y. R. Asian J. Org. Chem. 2019, 8, 1067.
Options
文章导航

/

〈 〉