SIOC English
有机化学
高级检索

有机化学 >

2018 , Vol. 38 >Issue 11: 2833 - 2857

DOI: https://doi.org/10.6023/cjoc201805028

综述与进展

Pd催化C(sp3)—H键活化构建杂环化合物的研究进展

  • 赵康 ,
  • 杨磊 ,
  • 刘建华 ,
  • 夏春谷
展开
  • a 中国科学院兰州化学物理研究所 羰基合成与选择氧化国家重点实验室 兰州 730000;
    b 中国科学院大学 北京 100049

收稿日期: 2018-05-13

  修回日期: 2018-06-26

  网络出版日期: 2018-07-24

基金资助

国家自然科学基金（Nos.21372231，21673260）资助项目.

收起

Recent Advances in the Synthesis of Heterocyclic Compounds via Pd-Catalyzed C(sp3)-H Bond Activation

  • Zhao Kang ,
  • Yang Lei ,
  • Liu Jianhua ,
  • Xia Chungu
Expand
  • a State Key Laboratory of Oxo Synthesis and Selective Oxidation, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, Lanzhou 730000;
    b University of Chinise Academy of Science, Beijing 100049

Received date: 2018-05-13

  Revised date: 2018-06-26

  Online published: 2018-07-24

Supported by

Project supported by the National Natural Science Foundation of China (Nos. 21372231, 21673260).

Fold

摘要

杂环类化合物是传统有机合成、农药和医药合成的重要中间体，也是构建若干具有生物活性天然产物的基本骨架.通过Pd催化的C（sp3）-H键活化实现一系列杂环化合物的合成，由于其具有高原子经济性的特点，近些年已发展成为杂环化合物合成领域的研究热点之一.根据所形成杂环化合物（主要涉及N、O杂环）的环数分类，综述了近十几年Pd催化C（sp3）-H键活化构建杂环化合物的研究进展，探讨了反应的选择性、底物兼容性和反应机理，并对该领域的现存局限性和发展前景进行了总结和展望.

关键词： Pd催化; C(sp3)-H键活化; 杂环

本文引用格式

赵康 , 杨磊 , 刘建华 , 夏春谷 . Pd催化C(sp3)—H键活化构建杂环化合物的研究进展[J]. 有机化学, 2018 , 38(11) : 2833 -2857 . DOI: 10.6023/cjoc201805028

Abstract

Heterocyclic compounds are not only important intermediates in organic synthesis and medicine synthesis, but also the basic building framework of biologically active natural products. In recent years, Pd-catalyzed C(sp3)-H bonds activation has been demonstrated as one of the hot topics in the field of heterocyclic compound synthesis because of its high atomic economic characteristics. Herein, the recent research progress in the construction of heterocyclic compounds via Pd-catalyzed C(sp3)-H bond activation is summarized according to the classification of the ring number of heterocyclic compounds (mainly including N, O heterocycles). The reaction selectivity, substrate compatibility, reaction mechanism, advantages and disadvantages as well as an outlook in this field are also discussed.

Key words： Pd-catalyzed; C (sp3)-H bond activation; heterocyclic compounds

参考文献

[1] (a) Brady, P. B.; Bhat, V. Eur. J. Org. Chem. 2017, 5179.
(b) Shaikh, T. M.; Hong, F.-E. J. Organomet. Chem. 2016, 801, 139.
(c) McMurray, L.; O'Hara, F.; Gaunt, M. J. Chem. Soc. Rev. 2011, 40, 1885.
(d) Pei, P.; Zhang, F.; Yi, H.; Lei, A. Acta Chim. Sinica 2017, 75, 15(in Chinese). (裴朋昆, 张凡, 易红, 雷爱文, 化学学报, 2017, 75, 15.)
[2] (a) Zeni, G.; Larock, R. C. Chem. Rev. 2004, 104, 2285.
(b) Patil, N. T.; Yamamoto, Y. Chem. Rev. 2008, 108, 3395.
[3] Murahashi, S. J. Am. Chem. Soc. 1955, 77, 6403.
[4] (a) Vitaku, E.; Smith, D. T.; Njardarson, J. T. J. Med. Chem. 2014, 57, 10257.
(b) Rueping, M.; Dufour, J.; Schoepke, F. R. Green Chem. 2011, 13, 1084.
[5] (a) Luo, P.; Tang, R.; Zhong, P.; Li, J. Chin. J. Org. Chem. 2009, 29, 1924(in Chinese). (罗培松, 汤日元, 钟平, 李金恒, 有机化学, 2009, 29, 1924.)
(b) Martins, M. A.; Frizzo, C. P.; Moreira, D. N.; Zanatta, N.; Bonacorso, H. G. Chem. Rev. 2008, 108, 2015.
(c) Chen, X.-H.; Wei, Q.; Luo, S.-W.; Xiao, H.; Gong, L.-Z. J. Am. Chem. Soc. 2009, 131, 13819.
[6] (a) Yang, Y.; Lan, J.; You, J. Chem. Rev. 2017, 117, 8787.
(b) Lyons, T. W.; Sanford, M. S. Chem. Rev. 2010, 110, 1147.
[7] (a) Jain, P.; Verma, P.; Xia, G.; Yu, J.-Q. Nat. Chem. 2017, 9, 140.
(b) Fumagalli, G.; Stanton, S.; Bower, J. F. Chem. Rev. 2017, 117, 9404.
[8] He, J.; Wasa, M.; Chan, K. S. L.; Shao, Q.; Yu, J.-Q. Chem. Rev. 2017, 117, 8754
[9] Baudoin, O. Acc. Chem. Res. 2017, 50, 1114.
[10] (a) Xu, J.; Wei, Z.; Li, J. Chin. J. Org. Chem. 2012, 32, 1208(in Chinese). (徐娟, 魏真, 李加荣, 有机化学, 2012, 32, 1208.)
(b) Zhu, Q.; Wang, L.; Xia, C.; Liu, C. Chin. J. Org. Chem. 2016, 36, 2813(in Chinese). (朱庆, 王露, 夏春谷, 刘超, 有机化学, 2016, 36, 2813.)
(c) Huang, J.; Gu, Q.; You, S. Chin. J. Org. Chem. 2018, 38, 51(in Chinese). (黄家翩, 顾庆, 游书力, 有机化学, 2018, 38, 51.)
(d) Wang, S.; Yan, F.; Wang, L.; Zhu, L. Chin. J. Org. Chem. 2018, 38, 291(in Chinese). (汪珊, 严沣, 汪连生, 朱磊, 有机化学, 2018, 38, 291.)
[11] McNally, A.; Haffemayer, B.; Collins, B. S.; Gaunt, M. J. Nature 2014, 510, 129.
[12] Smalley, A. P.; Gaunt, M. J. J. Am. Chem. Soc. 2015, 137, 10632.
[13] Zakrzewski, J.; Smalley, A. P.; Kabeshov, M. A.; Gaunt, M. J.; Lapkin, A. A. Angew. Chem., Int. Ed. 2016, 55, 8878.
[14] Smalley, A. P.; Cuthbertson, J. D.; Gaunt, M. J. J. Am. Chem. Soc. 2017, 139, 1412.
[15] He, G.; Zhao, Y.; Zhang, S.; Lu, C.; Chen, G. J. Am. Chem. Soc. 2012, 134, 3.
[16] Ye, X.; He, Z.; Ahmed, T.; Weise, K.; Akhmedov, N. G.; Petersen, J. L.; Shi, X. Chem. Sci. 2013, 4, 3712.
[17] (a) Lo, M. M.-C.; Fu, G. C. J. Am. Chem. Soc. 2002, 124, 4572.
(b) France, S.; Weatherwax, A.; Taggi, A. E.; Lectka, T. Acc. Chem. Res. 2004, 37, 592.
[18] Zhang, Q.; Chen, K.; Rao, W.-H.; Zhang, Y.; Chen, F.-J.; Shi, B.-F. Angew. Chem., Int. Ed. 2013, 52, 13588.
[19] Ling, P.-X.; Fang, S.-L.; Yin, X.-S.; Zhang, Q.; Chen, K.; Shi, B.-F. Chem. Commun. 2017, 53, 6351.
[20] Ting, C. P.; Maimone, T. J. Angew. Chem., Int. Ed. 2014, 126, 3179.
[21] Baudoin, O.; Herrbach, A.; Guéritte, F. Angew. Chem., Int. Ed. 2003, 115, 5914.
[22] Saget, T.; Cramer, N. Angew. Chem., Int. Ed. 2012, 51, 12842.
[23] Lafrance, M.; Gorelsky, S.; Fagnou, K. J. Am. Chem. Soc. 2007, 129, 14570.
[24] Nakanishi, M.; Katayev, D.; Besnard, C.; Kündig, E. P. Angew. Chem., Int. Ed. 2011, 50, 7438.
[25] Pedroni, J.; Boghi, M.; Saget, T.; Cramer, N. Angew. Chem., Int. Ed. 2014, 53, 9064.
[26] Dailler, D.; Rocaboy, R.; Baudoin, O. Angew. Chem., Int. Ed. 2017, 56, 7218.
[27] Sun, W.-W.; Cao, P.; Mei, R.-Q.; Li, Y.; Ma, Y.-L.; Wu, B. Org. Lett. 2014, 16, 480.
[28] Zhao, J.; Zhao, X.-J.; Cao, P.; Liu, J.-K.; Wu, B. Org. Lett. 2017, 19, 4880.
[29] Willcox, D.; Chappell, B. G. N.; Hogg, K. F.; Calleja, J.; Smalley, M. G.; Gaunt, M. J. Science 2016, 354, 851.
[30] Cabrera-Pardo, J. R.; Trowbridge, A.; Nappi, M.; Ozaki, K.; Gaunt, M. J. Angew. Chem., Int. Ed. 2017, 129, 12120.
[31] Hogg, K. F.; Trowbridge, A.; Álvarez−Pérez, A.; Gaunt, M. J. Chem. Sci. 2017, 8, 8198.
[32] Zhao, R.; Lu, W. Org. Lett. 2017, 19, 1768.
[33] Nadres, E. T.; Daugulis, O. J. Am. Chem. Soc. 2012, 134, 7.
[34] Wang, C.; Chen, C.; Zhang, J.; Han, J.; Wang, Q.; Guo, K.; Liu, P.; Guan, M.; Yao, Y.; Zhao, Y. Angew. Chem., Int. Ed. 2014, 53, 9884.
[35] Jiang, H.; He, J.; Liu, T.; Yu, J.-Q. J. Am. Chem. Soc. 2016, 138, 2055.
[36] He, C.; Gaunt, M. J. Chem. Sci. 2017, 8, 3586.
[37] (a) Meijere, A. D.; Zezschwitz, P. V.; Bräse, S. Acc. Chem. Res. 2005, 38, 413.
(b) Ikeda, S. I. Acc. Chem. Res. 2000, 33, 511.
[38] Ren, H.; Knochel, P. Angew. Chem., Int. Ed. 2006, 45, 3462.
[39] Ren, H.; Li, Z.; Knochel, P. Chem. Asian J. 2007, 2, 416.
[40] Watanabe, T.; Oishi, S.; Fujii, N.; Ohno, H. Org. Lett. 2008, 10, 1759.
[41] (a) Thu, H. Y.; Yu, W. Y.; Che, C. M. J. Am. Chem. Soc. 2006, 128, 9048.
(b) Liang, C.; Collet, F.; Robert-Peillard, F.; Müller, P.; Dodd, R. H.; Dauban, P. J. Am. Chem. Soc. 2008, 130, 343.
[42] Neumann, J. J.; Rakshit, S.; Dröge, T.; Glorius, F. Angew. Chem., Int. Ed. 2009, 48, 6892.
[43] Enders, D.; Niemeier, O.; Henseler, A. Chem. Rev. 2007, 107, 5606.
[44] Arduengo, A. J.; Harlow, R. L.; Kline, M. J. Am. Chem. Soc. 1991, 113, 361.
[45] Katayev, D.; Nakanishi, M.; Bürgi, T.; Kündig, E. P. Chem. Sci. 2012, 3, 1422.
[46] Larionov, E.; Nakanishi, M.; Katayev, D.; Besnard, C.; Kündig, E. P. Chem. Sci. 2013, 4, 1995.
[47] Katayev, D.; Larionov, E.; Nakanishi, M.; Besnard, C.; Kündig, E. P. Chem.-Eur. J. 2014, 20, 15021.
[48] Anas, S.; Cordi, A.; Kagan, H. B. Chem. Commun. 2011, 47, 11483.
[49] Guyonnet, M.; Baudoin, O. Org. Lett. 2012, 14, 398.
[50] Saget, T.; Lemouzy, S. J.; Cramer, N. Angew. Chem., Int. Ed. 2012, 51, 2238.
[51] Nanjo, T.; Tsukano, C.; Takemoto, Y. Org. Lett. 2012, 14, 4270.
[52] (a) Nelson, A. C.; Kalinowski, E. S.; Jacobson, T. L.; Grundt, P. Tetrahedron Lett. 2013, 54, 6804.
(b) Argade, S. D.; Argrade, N. P. Org. Lett. 2013, 15, 4006.
(c) Wang, C.; Zhang, L.; Ren, A.; Lu, P.; Wang, Y. Org. Lett. 2013, 15, 2982.
[53] Tsukano, C.; Okuno, M.; Nishiguchi, H.; Takemoto, Y. Adv. Synth. Catal. 2014, 356, 1533.
[54] (a) Shimizu, R.; Egami, H.; Nagi, T.; Chae, J.; Hamashima, Y.; Sodeoka, M. Tetrahedron Lett. 2010, 51, 5947.
(b) Cheng, Y.; Yuan, X.; Ma, J.; Yu, S. Chem.-Eur. J. 2015, 21, 8355.
[55] Pedroni, J.; Cramer, N. Org. Lett. 2016, 18, 1932.
[56] Leal, R. A.; Bischof, C.; Lee, Y. V.; Sawano, S.; McAtee, C. C.; Latimer, L. N.; Russ, Z. N.; Dueber, J. E.; Yu, J.-Q.; Sarpong, R. Angew. Chem., Int. Ed. 2016, 55, 11824.
[57] Zhang, S.; Lu, J.; Ye, J.; Duan, W.-L. Chin. J. Org. Chem. 2016, 36, 752(in Chinese). (张松, 陆俊筑, 叶金星, 段伟良, 有机化学, 2016, 36, 752.)
[58] Yang, L.; Melot, R.; Neuburger, M.; Baudoin, O. Chem. Sci. 2017, 8, 1344.
[59] Salcedo, A.; Neuville. L.; Zhu, J. J. Org. Chem. 2008, 73, 3600.
[60] Liégault, B.; Fangou, K. Organometallics 2008, 27, 4841.
[61] Rousseaux, S.; Gorelsky, S. I.; Chung, B. K. W.; Fagnou, K. J. Am. Chem. Soc. 2010, 132, 10692.
[62] Yoo, E. J.; Wasa, M.; Yu, J.-Q. J. Am. Chem. Soc. 2010, 132, 17378.
[63] Wasa, M.; Engle, K. M.; Yu, J.-Q. J. Am. Chem. Soc. 2010, 132, 3680.
[64] Tsukano, C.; Okuno, M.; Takemoto, Y. Angew. Chem., Int. Ed. 2012, 51, 2763.
[65] Zhang, Q.; Yu, H.-Z.; Fu, Y. Organometallics 2013, 32, 4165.
[66] He, G.; Zhang, S.-Y.; Nack, W. A.; Li, Q.; Chen, G. Angew. Chem., Int. Ed. 2013, 52, 11124.
[67] Zhang, M. J. Chem. Res. 2013, 37, 606.
[68] (a) Nair, J. J.; Aremu, A. O.; Van Staden, J. J. Ethnopharmacol. 2011, 137, 1102.
(b) Evdokimov, N. M.; Lamoral-Theys, D.; Mathieu, V.; Andolfi, A.; Frolova, L. V.; Pelly, S. C.; Van Otterlo, W. A.; Magedov, I. V.; Kiss, R.; Evidente, A.; Kornienko, A. Bioorg. Med. Chem. 2011, 19, 7252.
(c) Evidente, A.; Kornienko, A. Phytochem. Rev. 2009, 8, 449.
[69] (a) De, S.; Mishra, S.; Kakde, B. N.; Dey, D.; Bisai, A. J. Org. Chem. 2013, 78, 7823.
(b) De, S.; Ghosh, S.; Bhunia, S.; Sheikh, J. A.; Bisai, A. Org. Lett. 2012, 14, 4466.
[70] Tsukano, C.; Muto, N.; Enkhtaivan, I.; Takemoto, Y. Chem. Asian J. 2014, 9, 2628.
[71] Holstein, P. M.; Dailler, D.; Vantourout, J.; Shaya, J.; Millet, A.; Baudoin, O. Angew. Chem., Int. Ed. 2015, 55, 2805.
[72] Calleja, J.; Pla, D.; Gorman, T. W.; Domingo, V.; Haffemayer, B.; Gaunt, M. J. Nat. Chem. 2015, 7, 1009.
[73] Wang, C.; Zhang, L.; Chen, C.; Han, J.; Yao, Y.; Zhao, Y. Chem. Sci. 2015, 6, 4610.
[74] Wang, P.-L.; Li, Y.; Wu, Y.; Li, C.; Lan, Q.; Wang, X.-S. Org. Lett. 2015, 17, 3698.
[75] Hernando, E.; Villalva, J.; Martínez, Á. M.; Alonso, I.; Rodríguez, N.; Gómez Arrayás, R.; Carretero, J. C. ACS Catal. 2016, 6, 6868.
[76] Parella, R.; Babu, S. A. J. Org. Chem. 2017, 82, 7123.
[77] Tsukano, C.; Okuno, M.; Takemoto, Y. Chem. Lett. 2013, 42, 753.
[78] Ladd, C. L.; Roman, D. S.; Charette, A. B. Org. Lett. 2013, 15, 1350.
[79] Pedroni, J.; Cramer, N. Angew. Chem., Int. Ed. 2015, 54, 11826.
[80] Saget, T.; Perez, D.; Cramer, N. Org. Lett. 2013, 15, 1354.
[81] Zhang, M.; Jovic, F.; Vickers, T.; Dyck, B.; Tamiya, J.; Grey, J.; Tran, J. A.; Fleck, B. A.; Pick, R.; Foster, A. C.; Chen, C. Bioorg. Med. Chem. Lett. 2008, 18, 3682.
[82] Krow, G. R.; Cannon, K. C. Org. Prep. Proced. Int. 2000, 32, 103.
[83] Micheli, F.; Cavanni, P.; Arban, R.; Benedetti, R.; Bertani, B.; Bettati, M.; Bettelini, L.; Bonanomi, G.; Braggio, S.; Checchia, A.; Davalli, S.; Di Fabio, R.; Fazzolari, E.; Fontana, S.; Marchioro, C.; Minick, D.; Negri, M.; Oliosi, B.; Read, K. D.; Sartori, I.; Tedesco, G.; Tarsi, L.; Terreni, S.; Visentini, F.; Zocchi, A.; Zonzini, L. J. Med. Chem. 2010, 53, 2534.
[84] Pedroni, J.; Cramer, N. J. Am. Chem. Soc. 2017, 139, 12398.
[85] Fraunhoffer, K. J.; White, M. C. J. Am. Chem. Soc. 2007, 129, 7274.
[86] (a) Du, H.; Yuan, W.; Zhao, B.; Shi, Y. J. Am. Chem. Soc. 2007, 129, 7496.
(b) Bar, G. L. J.; Lloyd-Jones, G. C.; Booker-Milburn, K. I. J. Am. Chem. Soc. 2005, 127, 7308.
[87] Du, H.; Zhao, B.; Shi, Y. J. Am. Chem. Soc. 2008, 130, 8590.
[88] Fu, R.; Zhao, B.; Shi, Y. J. Org. Chem. 2009, 74, 7577.
[89] Stowers, K. J.; Fortner, K. C.; Sanford, M. S. J. Am. Chem. Soc. 2011, 133, 6541.
[90] Sofack-Kreutzer, J.; Martin, N.; Renaudat, A.; Jazzar, R.; Baudoin, O. Angew. Chem., Int. Ed. 2012, 51, 10399.
[91] (a) Dailler, D.; Danoun, G.; Baudoin, O. Angew. Chem., Int. Ed. 2015, 54, 4919.
(b) Dailler, D.; Danoun, G.; Ourri, B.; Baudoin, O. Chem. Eur. J. 2015, 21, 9370.
[92] Miki, Y.; Umemoto, H.; Dohshita, M.; Hamamoto, H. Tetrahedron Lett. 2012, 53, 1924.
[93] Rousseaux, S.; Davi, M.; Sofack-Kreutzer, J.; Pierre, C.; Kefalidis, C. E.; Clot, E.; Fagnou, K.; Baudoin, O. J. Am. Chem. Soc. 2010, 132, 10706.
[94] Strambeanu, I. I.; White, M. C. J. Am. Chem. Soc. 2013, 135, 12032.
[95] Osberger, T. J.; White, M. C. J. Am. Chem. Soc. 2014, 136, 11176.
[96] (a) Meyers, A. I. Acc. Chem. Res. 1978, 11, 375.
(b) Lipshutz, B. H. Chem. Rev. 1986, 86, 795.
(c) Gomez, M.; Muller, G.; Rocamora, M. Coord. Chem. Rev. 1999, 193, 769.
(d) Liao, S.; Sun, X.-L.; Tang, Y. Acc. Chem. Res. 2014, 47, 2260.
(e) Giri, R.; Chen, X.; Yu, J.-Q. Angew. Chem., Int. Ed. 2005, 44, 2112.
[97] Frump, J. A. Chem. Rev. 1971, 71, 483.
[98] Li, B.; Wang, S.-Q.; Liu, B.; Shi, B.-F. Org. Lett. 2015, 17, 1200.
[99] (a) Mitsunobu, O. In Comprehensive Organic Synthesis, Eds.:Fleming, I.; Trost, B. M., Pergamon, Oxford, 1991, p. 1.
(b) Smith, M. B.; March, J. Advanced Organic Chemistry, Wiley Interscience, New York, 2001, p. 479.
[100] Thompson, S. J.; Thach, D. Q.; Dong, G. J. Am. Chem. Soc. 2015, 137, 11586.
[101] Lee, J. M.; Chang, S. Tetrahedron Lett. 2006, 47, 1375.
[102] Novák, P.; Correa, A.; Gallardo−Donaire, J.; Martin, R. Angew. Chem., Int. Ed. 2011, 50, 12236.
[103] Eom, D.; Jeong, Y.; Kim, Y. R.; Lee, E.; Choi, W.; Lee, P. H. Org. Lett. 2013, 15, 5210.
[104] Shi, B.-F.; Liu, B. Synlett 2016, 27, 2396.
[105] Wang, H.; Niu, Y.; Zhang, G.; Ye, X.-S. Tetrahedron Lett. 2016, 57, 4544.
[106] McCallum, M. E.; Rasik, C. M.; Wood, J. L.; Brown, M. K. J. Am. Chem. Soc. 2016, 138, 2437.
[107] Dangel, B. D.; Godula, K.; Youn, S. W.; Sezen, B.; Sames, D. J. Am. Chem. Soc. 2002, 124, 11856.
[108] Rice, G. T.; White, M. C. J. Am. Chem. Soc. 2009, 131, 11707.
[109] Nahra, F.; Liron, F.; Prestat, G.; Mealli, C.; Messaoudi, A.; Poli, G. Chem. Eur. J. 2009, 15, 11078.
[110] Qi, X. B.; Rice, G. T.; Lall, M. S.; Plummer, M. S.; White, M. C. Tetrahedron. 2010, 66, 4816.
[111] Zaitsev, V. G.; Shabashov, D.; Daugulis, O. J. Am. Chem. Soc. 2005, 127, 13154.
[112] Feng, Y.; Wang, Y.; Landgraf, B.; Liu, S.; Chen, G. Org. Lett. 2010, 12, 3414.
[113] Yan, J.-X.; Li, H.; Liu, X.-W.; Shi, J.-L.; Wang, X.; Shi, Z.-J. Angew. Chem., Int. Ed. 2014, 53, 4945.
[114] Deng, Y.; Gong, W.; He, J.; Yu, J.-Q. Angew. Chem., Int. Ed. 2014, 53, 6692.
[115] Liu, W.; Yu, Q.; Hu, L.; Chen, Z.; Huang, J. Chem. Sci. 2015, 6, 5768.
[116] Guan, M.; Pang, Y.; Zhang, J.; Zhao, Y. Chem. Commun. 2016, 52, 7043.
[117] Chen, K.; Hu, F.; Zhang, S.-Q.; Shi, B.-F. Chem. Sci. 2013, 4, 3906.
[118] Ruan, Z.; Sauermann, N.; Manoni, E.; Ackermann, L. Angew. Chem., Int. Ed. 2017, 56, 3172.
[119] Yoshioka, S.; Nagatomo, M.; Inoue, M. Org. Lett. 2015, 17, 90.
[120] Boultadakis-Arapinis, M.; Lemoine, P.; Turcaud, S.; Micouin, L.; Lecourt, T. J. Am. Chem. Soc. 2010, 132, 15477.
[121] Probst, N.; Grelier, G.; Ghermani, N.; Gandon, V.; Alami, M.; Messaoudi, S. Org. Lett. 2017, 19, 5038.
[122] Wang, P.-S.; Shen, M.-L.; Wang, T.-C.; Lin, H.-C.; Gong, L.-Z. Angew. Chem., Int. Ed. 2017, 56, 16032.
[123] Rousseaux, S.; Liégault, B.; Fagnou, K. Chem. Sci. 2012, 3, 244.
[124] Pedroni, J.; Saget, T.; Donets, P. A.; Cramer, N. Chem. Sci. 2015, 6, 5164.
[125] Ladd, C. L.; Belouin, A. V.; Charette, A. B. J. Org. Chem. 2016, 81, 256.
[126] Ladd, C. L.; Charette, A. B. Org. Lett. 2016, 18, 6046.
[127] Dyker, G. Angew. Chem., Int. Ed. 1992, 31, 1023.
[128] (a) Dyker, G. J. Org. Chem. 1993, 58, 6426.
(b) Dyker, G. Chem. Ber. 1994, 127, 739.
[129] Gormisky, P. E.; White, M. C. J. Am. Chem. Soc. 2011, 133, 12584.
[130] Ammann, S. E.; Rice, G. T.; White, M. C. J. Am. Chem. Soc. 2014, 136, 10834.
[131] Wang, P.-S.; Liu, P.; Zhai, Y.-J.; Lin, H.-C.; Han, Z.-Y.; Gong, L.-Z. J. Am. Chem. Soc. 2015, 137, 12732.
[132] Ammann, S. E.; Liu, W.; White, M. C. Angew. Chem., Int. Ed. 2016, 55, 9571.
[133] Fraunhoffer, K. J.; Prabagaran, N.; Sirois, L. E.; White, M. C. J. Am. Chem. Soc. 2006, 128, 9032.
[134] Wu, L.; Qiu, S.; Liu, G. Org. Lett. 2009, 11, 2707.
[135] Stang, E. M.; White, M. C. Nat. Chem. 2009, 1, 547.
[136] Stang, E. M.; White, M. C. Angew. Chem., Int. Ed. 2011, 50, 2094.
[137] Ladd, C. L.; Roman, D. S.; Charette, A. B. Tetrahedron 2013, 69, 4479.

Options
文章导航

/

〈 〉