钯催化的烯烃异构化反应
收稿日期: 2021-09-28
修回日期: 2021-11-03
网络出版日期: 2021-11-17
基金资助
国家自然科学基金(22171277); 国家自然科学基金(22101291); 国家自然科学基金(21821002); 上海“启明星”(20QA1411400)
Pd-Catalyzed Isomerization of Alkenes
Received date: 2021-09-28
Revised date: 2021-11-03
Online published: 2021-11-17
Supported by
National Natural Science Foundation of China(22171277); National Natural Science Foundation of China(22101291); National Natural Science Foundation of China(21821002); Shanghai Rising-Star Program(20QA1411400)
陈宏超 , 吴奕晨 , 于洋 , 王鹏 . 钯催化的烯烃异构化反应[J]. 有机化学, 2022 , 42(3) : 742 -757 . DOI: 10.6023/cjoc202109045
Starting from commercially available simple olefins, alkene isomerization could realize the efficient construction of multi-substituted alkenes, which might be difficult to access with other synthetic methods, in an atom-economic manner via the stereoselective or positional-selective modulation of the carbon-carbon double bonds. The palladium catalyzed stereoselective (Z/E) and the positional selective isomerization reactions of alkenes are summarized. The mechanistic perspectives, and their synthetic applications in the synthesis of drug molecules and natural products are discussed in detail.
Key words： palladium catalysis; alkene; carbon-carbon bond; isomerization
| [1] | Larsen, C. R.; Grotjahn, D. B. In Applied Homogeneous Catalysis with Organometallic Compounds: A Comprehensive Handbook in Four Volumes, Eds.: Cornils, B.; Herrmann, W. A.; Beller, M.; Paciello, R., 2017, Wiley, pp. 1365-1378. |
| [2] | (a) AlMaadeed, M. A.-A.; Krupa, I. Polyolefin Compounds and Materials, Springer, Heidelberg, 2016. |
| [2] | (b) Severn, J. R.; Chadwick, J. C. Tailor-Made Polymers, Wiley- VCH, Weinheim, 2008. |
| [2] | (c) Sauter, D. W.; Taoufik, M.; Boisson, C. Polymers 2017, 9, 185. |
| [2] | (d) Guan, Z. B.; Popeney, C. S. Top. Organomet. Chem. 2009, 26, 179. |
| [2] | (e) Flisak, Z.; Sun, W. H. ACS Catal. 2015, 5, 4713. |
| [2] | (f) Makio, H.; Terao, H.; Iwashita, A.; Fujita, T. Chem. Rev. 2011, 111, 2363. |
| [2] | (g) Collins, R. A.; Russell, A. F.; Mountford, P. Appl. Petrochem. Res. 2015, 5, 153. |
| [2] | (h) Gibson, V. C.; Solan, G. A. Top. Organomet. Chem. 2009, 26, 107. |
| [2] | (i) Mu, H.; Pan, L.; Song, D.; Li, Y. Chem. Rev. 2015, 115, 12091. |
| [2] | (j) Chen, C. Nat. Rev. Chem. 2018, 2, 6. |
| [3] | (a) Besse, P.; Veschambre, H. Tetrahedron 1994, 50, 8885. |
| [3] | (b) Johnson, R. A.; Sharpless, K. B. In Catalytic Asymmetric Synthesis, Ed.: Ojima, I., Wiley-VCH, New York, 2000, pp. 229-280. |
| [3] | (c) Bonini, C.; Righi, G. A. Tetrahedron 2002, 58, 4981. |
| [3] | (d) Xia, Q.-H.; Ge, H.-Q.; Ye, C.-P.; Liu, Z.-M.; Su, K.-X. Chem. Rev. 2005, 105, 1603. |
| [3] | (e) Adolfsson, H. In Modern Oxidation Methods, Ed.: Bäckvall, J.-E., Wiley-VCH, Weinheim, 2010, pp. 21-49. |
| [3] | (f) De Faveri, G.; Ilyashenko, G.; Watkinson, M. Chem. Soc. Rev. 2011, 40, 1722. |
| [3] | (g) Feng, X. Q.; Du, H. F. Chin. J. Chem. 2021, 39, 2016. |
| [4] | (a) Cerveny, L. Catalytic Hydrogenation, Elsevier, Amsterdam, 1986. |
| [4] | (b) Rylander, P. The Catalytic Hydrogenation in Organic Syntheses, Ed.: Rylander, P., Academic Press, Inc, San Diego, 1979, pp. 31-63. |
| [4] | (c) Nishimura, S. Handbook of Heterogeneous Catalytic Hydrogenation for Organic Synthesis, Wiley-VCH Verlag GmbH, New York, 2001. |
| [4] | (d) de Vries, J. G.; Elsevier, C. J. The Handbook of Homoge-neous Hydrogenation, WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim, 2008. |
| [4] | (e) Xie, J.-H.; Zhou, Q.-L. Acta Chim. Sinica 2012, 70, 1427. (in Chinese) |
| [4] | (谢建华, 周其林, 化学学报, 2012, 70, 1427.) |
| [4] | (f) Zhao, D.; Candish, L.; Paul, D.; Glorius, F. ACS Catal. 2016, 6, 5978. |
| [4] | (g) Seo, C. S. G.; Morris, R. H. Organometallics 2019, 38, 47. |
| [4] | (h) Verendel, J. J.; Pamies, O. P.; Diéguez, M.; Andersson, P. G. Chem. Rev. 2014, 114, 2130. |
| [5] | (a) Cabri, W.; Candiani, I. Acc. Chem. Res. 1995, 28, 2. |
| [5] | (b) de Meijere, A.; Meyer, F. E. Angew. Chem., nt. Ed. 1995, 33, 2379. |
| [5] | (c) Beletskaya, I. P.; Cheprakov, A. V. Chem. Rev. 2000, 100, 3009. |
| [5] | (d) Dounay, A. B.; Overman, L. E. Chem. Rev. 2003, 103, 2945. |
| [5] | (e) Nicolaou, K. C.; Bulger, P. G.; Sarlah, D. Angew. Chem., nt. Ed. 2005, 44, 4442. |
| [5] | (f) Polshettiwar, V.; Molnár, Á. Tetrahedron 2007, 63, 6949. |
| [5] | (g) Le Bras, J.; Muzart, J. Chem. Rev. 2011, 111, 1170. |
| [5] | (h) Ruan, J.; Xiao, J. Acc. Chem. Res. 2011, 44, 614. |
| [5] | (i) McCartney, D.; Guiry, P. J. Chem. Soc. Rev. 2011, 40, 5122. |
| [5] | (j) Sigman, M. S.; Werner, E. W. Acc. Chem. Res. 2012, 45, 874. |
| [5] | (k) Wang, S.-S.; Yang, G.-Y. Catal. Sci. Technol. 2016, 6, 2862. |
| [5] | (l) Roy, D.; Uozumi, Y. Adv. Synth. Catal. 2018, 360, 602. |
| [5] | (m) Gao, S. Q.; Shi, L. L.; Chang, L.; Wang, B. L.; Fu, J. K. Synthesis 2021, 53, 861. |
| [6] | (a) Żukowska, K. Olefin Metathesis: Theory and Practice, Ed.: Grela, K., Wiley, New Jersey, 2014, pp. 39-73. |
| [6] | (b) Basset, J. M.; Callens, E.; Riache, N. Handbook of Metathesis, Vol. 1, Eds.: Grubbs, R. H.; Wenzel, A. G., Wiley-VCH, Weinheim, 2015, pp. 33-70. |
| [6] | (c) Copéret, C.; Berkson, Z. J.; Chan, K. W.; Silva, J. D. J.; Gordon, C. P.; Pucino, M.; Zhizhko, P. A. Chem. Sci. 2021, 12, 3092. |
| [7] | (a) Legnani, L.; Bhawal, B. N.; Morandi, B. Synthesis 2017, 776. |
| [7] | (b) van der Vlugt, J. I. Chem. Soc. Rev. 2010, 39, 2302. |
| [7] | (c) Müller, T. E.; Hultzsch, K. C.; Yus, M.; Foubelo, F.; Tada, M. Chem. Rev. 2008, 108, 3795. |
| [7] | (d) Müller, T. E.; Beller, M. Chem. Rev. 1998, 98, 675. |
| [7] | (e) Huang, L.; Arndt, M.; Gooßen, K.; Heydt, H. H.; Gooßen, L. J. Chem. Rev. 2015, 115, 2596. |
| [7] | (f) Wu, Z. Y.; Hu, M.; Li, J. X.; Wu, W. Q.; Jiang, H. F. Org. Biomol. Chem. 2021, 19, 3036. |
| [7] | (g) Streiff, S.; Jérôme, F. Chem. Soc. Rev. 2021, 50, 1512. |
| [8] | (a) Carroll, A.; O’Sullivan, T. P.; Guiry, P. J. Adv. Synth. Catal. 2005, 347, 609. |
| [8] | (b) Beletskaya, I.; Pelter, A. Tetrahedron 1997, 53, 4957. |
| [8] | (c) Burgess, K.; Ohlmeyer, M. J. Chem. Rev. 1991, 91, 1179. |
| [8] | (d) Vogels, C. M.; Westcott, S. A. Curr. Org. Chem. 2005, 9, 687. |
| [8] | (e) Chen, J.; Lu, Z. Org. Chem. Front. 2018, 5, 260. |
| [8] | (f) Chen, J.; Guo, J.; Lu, Z. Chin. J. Chem. 2018, 36, 1075. |
| [8] | (g) Wen, H.; Liu, G.; Huang, Z. Coord. Chem. Rev. 2019, 386, 138. |
| [8] | (h) Wei, D.; Darcel, C. Chem. Rev. 2019, 119, 2550. |
| [8] | (i) Obligacion, J. V.; Chirik, P. J. Nat. Rev. Chem. 2018, 2, 15. |
| [8] | (j) Fan, W. W.; Li, L.; Zhang, G. Q. J. Org. Chem. 2019, 84, 5987. |
| [8] | (k) Wang, X. J.; Wang, Y.; Huang, W.; Xia, C. G.; Wu, L. P. ACS Catal. 2021, 11, 1. |
| [9] | Zhou, C.; Mao, W. X. Chem. Ind. Eng. Prog. 2009, 28, 1313. (in Chinese) |
| [9] | (周丛, 茅文星, 化工进展, 2009, 28, 1313.) |
| [10] | (a) Larionov, E.; Li, H.; Mazet, C. Chem. Commun. 2014, 50, 9816. |
| [10] | (b) Liu, X. F.; Li, B.; Liu, Q. Synthesis 2019, 51, 1293. |
| [11] | (a) Casey, C. P.; Cyr, C. R. J. Am. Chem. Soc. 1973, 95, 2248. |
| [11] | (b) Tooley, P. A.; Arndt, L. W.; Darensbourg, M. Y. J. Am. Chem. Soc. 1985, 107, 2422. |
| [11] | (c) Reddy, M. R.; Periasamy, M. J. Organomet. Chem. 1995, 491, 263. |
| [11] | (d) Crivello, J. V.; Kong, S. Q. J. Org. Chem. 1998, 63, 6745. |
| [11] | (e) De Pasquale, R. J. Synth. Commun. 2006, 10, 225. |
| [11] | (f) Jennerjahn, R.; Jackstell, R.; Piras, I.; Franke, R.; Jiao, H.; Bauer, M.; Beller, M. ChemSusChem 2012, 5, 734. |
| [11] | (g) Yu, X.; Zhao, H.; Li, P.; Koh, M. J. J. Am. Chem. Soc. 2020, 142, 18223. |
| [12] | (a) Karapinka, G. L.; Orchin, M. J. Org. Chem. 1961, 26, 4187. |
| [12] | (b) Roos, L.; Orchin, M. J. Am. Chem. Soc. 1965, 87, 5502. |
| [12] | (c) Mc Cormack, W. E.; Orchin, M. J. Organomet. Chem. 1977, 129, 127. |
| [12] | (d) Onishi, M.; Oishi, S.; Sakaguchi, M. Takaki, I.; Hiraki, K. Bull. Chem. Soc. Jpn. 1986, 59, 3925. |
| [12] | (e) Onishi, M.; Hiraki, K.; Ishida, Y.; Dakeshita, K. Chem. Lett. 1986, 15, 333. |
| [12] | (f) Satyanarayana, N.; Periasamy, M. J. Organomet. Chem. 1987, 319, 113. |
| [12] | (g) Kobayashi, T.; Yorimitsu, H.; Oshima, K. Asian J. Org. Chem. 2009, 4, 1078. |
| [12] | (h) Punner, F.; Schmidt, A.; Hilt, G. Angew. Chem., nt. Ed. 2012, 51, 1270. |
| [12] | (i) Schmidt, A.; Hilt, G. Asian J. Org. Chem. 2014, 9, 2407. |
| [12] | (j) Chen, C.; Dugan, T. R.; Brennessel, W. W.; Weix, D. J.; Holland, P. L. J. Am. Chem. Soc. 2014, 136, 945. |
| [12] | (k) Crossley, S. W.; Barabe, F.; Shenvi, R. A. J. Am. Chem. Soc. 2014, 136, 16788. |
| [12] | (l) Schmidt, A.; Nodling, A. R.; Hilt, G. Angew. Chem., nt. Ed. 2015, 54, 801. |
| [12] | (m) Li, G.; Kuo, J. L.; Han, A.; Abuyuan, J. M.; Young, L. C.; Norton, J. R.; Palmer, J. H. J. Am. Chem. Soc. 2016, 138, 7698. |
| [12] | (n) Liu, X.; Zhang, W.; Wang, Y.; Zhang, Z.-X.; Jiao, L.; Liu, Q. J. Am. Chem. Soc. 2018, 140, 6873. |
| [12] | (o) Meng, Q.-Y.; Schirmer, T. E.; Katou, K.; König, B. Angew. Chem., nt. Ed. 2019, 58, 5723. |
| [12] | (p) Ai, W.; Zhong, R.; Liu, X.; Liu, Q. Chem. Rev. 2019, 119, 2876. |
| [13] | (a) Kanai, H. J. Chem. Soc., hem. Commun. 1972, 203. |
| [13] | (b) Tolman, A. C. J. Am. Chem. Soc. 1972, 94, 2994. |
| [13] | (c) Kanai, H.; Kushi, K.; Sakanoue, K.; Kishimoto, N. Bull. Chem. Soc. Jpn. 1980, 53, 2711. |
| [13] | (d) Bontempelli, G.; Daniele, S.; Schiavon, G.; Fiorani, M. Transition Met. Chem. 1987, 12, 292. |
| [13] | (e) Bontempelli, G.; Fiorani, M.; Daniele, S.; Schiavon, G. J. Mol. Catal. A: Chem. 1987, 40, 9. |
| [13] | (f) Bricout, H.; Mortreux, A.; Monflier, E. J. Organomet. Chem. 1998, 553, 469. |
| [13] | (g) Wille, A.; Tomm, S.; Frauenrath, H. Synthesis 1998, 305. |
| [13] | (h) Lochow, C. F.; Miller, R. G. J. Org. Chem. 1976, 41, 3020. |
| [13] | (i) D’Aniello, M. J., Jr; Barefield, E. K. J. Am. Chem. Soc. 2002, 100, 1474. |
| [13] | (j) Zhang, J.; Gao, H.; Ke, Z.; Bao, F.; Zhu, F.; Wu, Q. J. Mol. Catal. A: Chem. 2005, 231, 27. |
| [13] | (k) Wang, L.; Liu, C.; Bai, R.; Pan, Y.; Lei, A. Chem. Commun. 2013, 49, 7923. |
| [13] | (l) Weber, F.; Schmidt, A.; Röse, P.; Fischer, M.; Burghaus, O.; Hilt, G. Org. Lett. 2015, 17, 2952. |
| [13] | (m) Halli, J.; Kramer, P.; Bechthold, M.; Manolikakes, G. Adv. Synth. Catal. 2015, 357, 3321. |
| [13] | (n) Kapat, A.; Sperger, T.; Guven, S.; Schoenebeck, F. Science 2019, 363, 391. |
| [14] | (a) Hudson, B.; Taylor, P. C.; Webster, D. E.; Wells, P. B. Discuss. Faraday Soc. 1968, 46, 37. |
| [14] | (b) McGrath, D. V.; Grubbs, R. H.; Ziller, J. W. J. Am. Chem. Soc. 1991, 113, 3611. |
| [14] | (c) Wakamatsu, H.; Nishida, M.; Adachi, N.; Mori, M. J. Org. Chem. 2000, 65, 3966. |
| [14] | (d) Hu, Y.-J.; Dominique, R.; Das, S. K.; Roy, R. Can. J. Chem. 2000, 78, 838. |
| [14] | (e) Krompiec, S.; Pigulla, M.; Szczepankiewicz, W.; Bieg, T.; Kuznik, N.; Leszczynska-Sejda, K.; Kubicki, M.; Borowiak, T. Tetrahedron Lett. 2001, 42, 7095. |
| [14] | (f) Arisawa, M.; Terada, Y.; Nakagawa, M.; Nishida, A. Angew. Chem.,Int. Ed. 2002, 41, 4732. |
| [14] | (g) Arisawa, M.; Terada, Y.; Takahashi, K.; Nakagawa, M.; Nishida, A. J. Org. Chem. 2006, 71, 4255. |
| [14] | (h) Hanessian, S.; Giroux, S.; Larsson, A. Org. Lett. 2006, 8, 5481. |
| [14] | (i) Sharma, S. K.; Srivastava, V. K.; Jasra, R. V. J. Mol. Catal. A: Chem. 2006, 245, 200. |
| [14] | (j) Grotjahn, D. B.; Larsen, C. R.; Gustafson, J. L.; Nair, R.; Sharma, A. J. Am. Chem. Soc. 2007, 129, 9592. |
| [14] | (k) Larsen, C. R.; Grotjahn, D. B. J. Am. Chem. Soc. 2012, 134, 10357. |
| [14] | (l) Larsen, C. R.; Erdogan, G.; Grotjahn, D. B. J. Am. Chem. Soc. 2014, 136, 1226. |
| [14] | (m) Paulson, E. R.; Moore, C. E.; Rheingold, A. L.; Pullman, D. P.; Sindewald, R. W.; Cooksy, A. L.; Grotjahn, D. B. ACS Catal. 2019, 9, 7217. |
| [15] | (a) K. Stille, J.; Becker, Y J. Org. Chem. 1980, 45, 2139. |
| [15] | (b) Sasson, Y.; Zoran, A.; Blum, J. J. Mol. Catal. 1981, 11, 293. |
| [15] | (c) Tani, K.; Yamagata, T.; Akutagawa, S.; Kumobayashi, H.; Taketomi, T.; Takaya, H.; Miyashita, A.; Noyori, R.; Otsuka, S. J. Am. Chem. Soc. 1984, 106, 5208. |
| [15] | (d) Bergens, S. H.; Bosnich, B. J. Am. Chem. Soc. 1991, 113, 958. |
| [15] | (e) Alphonse, F. A.; Yudin, A. K. J. Am. Chem. Soc. 2006, 128, 11754. |
| [15] | (f) Tsang, D. S.; Yang, S.; Alphonse, F.-A.; Yudin, A. K. Chem.-Eur. J. 2008, 14, 886. |
| [15] | (g) Zhuo, L. G.; Yao, Z. K.; Yu, Z. X. Org. Lett. 2013, 15, 4634. |
| [15] | (h) Yip, S. Y. Y.; Aïssa, C. Angew. Chem., nt. Ed. 2015, 54, 6870. |
| [16] | (a) Baudry, D.; Ephritikhine, M.; Felkin, H. J. Chem. Soc., hem. Commun. 1978, 694. |
| [16] | (b) Yamamoto, Y.; Miyairi, T.; Ohmura, T.; Miyaura, N. J. Org. Chem. 1999, 64, 296. |
| [16] | (c) Yamamoto, R.; Fujikawa, N.; Miyaura, N. Synth. Commun. 2000, 30, 2383. |
| [16] | (d) Baxendale, I. R.; Lee, A. L.; Ley, S. V. J. Chem. Soc., erkin Trans. 1. 2002, 1850. |
| [16] | (e) Neugnot, B.; Cintrat, J. C. Rousseau, B. Tetrahedron 2004, 60, 3575. |
| [16] | (f) Chianese, A. R.; Shaner, S. E.; Tendler, J. A.; Pudalov, D. M.; Shopov, D. Y.; Kim, D.; Rogers, S. L.; Mo, A. Organometallics 2012, 31, 7359. |
| [16] | (g) Knapp, S. M. M.; Shaner, S. E.; Kim, D.; Shopov, D. Y.; Tendler, J. A.; Pudalov, D. M.; Chianese, A. R. Organometallics 2014, 33, 473. |
| [16] | (h) Wang, Y.; Qin, C.; Jia, X.; Leng, X.; Huang, Z. Angew. Chem., nt. Ed. 2017, 56, 1614. |
| [17] | (a) Smidt, J.; Hafner, W.; Jira, R.; Sedlmeier, J.; Sieber, R.; R€uttinger, R.; Kojer, H. Angew. Chem. 1959, 71, 176. |
| [17] | (b) Smidt, J.; Hafner, W.; Jira, R.; Sieber, R.; Sedlmeier, J.; Sabel, A. Angew. Chem.,Int. Ed. 1962, 1, 80. |
| [17] | (c) Jira, R. Angew. Chem., nt. Ed. 2009, 48, 9034. |
| [18] | Matsuura, R.; Karunananda, M. K.; Liu, M.; Nguyen, N.; Blackmond, D. G.; Engle, K. M. ACS Catal. 2021, 11, 4239. |
| [19] | Harrod, J. F.; Chalk, A. J. J. Am. Chem. Soc. 1964, 86, 1776. |
| [20] | Cramer, R.; Lindsey, R. V. J. Am. Chem. Soc. 1966, 88, 3534. |
| [21] | (a) Cruikshank, B.; Davies, N. R. Aust. J. Chem. 1966, 19, 815. |
| [21] | (b) Davies, N. R.; Dimichiel, A. D.; Pickle, V. A. Aust. J. Chem. 1968, 21, 385. |
| [21] | (c) Cruikshank, B.; Davies, N. R. Aust J. Chem. 1973, 26, 1935. |
| [22] | (a) Sen, A.; Lai, T. W. Inorg. Chem. 1981, 20, 4036. |
| [22] | (b) Sen, A.; Lai, T. W. Inorg. Chem. 1984, 23, 3257. |
| [23] | (a) Davies, N. R. Aust. J. Chem. 1964, 17, 212. |
| [23] | (b) Davies, N. R. Nature 1964, 201, 490. |
| [24] | Harrod, J. F.; Chalk, A. J. J. Am. Chem. Soc. 1966, 88, 3491. |
| [25] | Bingham, D.; Hudson, B.; Webster, D. E.; Wells, P. B. J. Chem. Soc., alton Trans. 1974, 1521. |
| [26] | Fan, J. M.; Wan, C. F.; Wang, Q.; Gao, L. F.; Zheng, X. Q.; Wang, Z. Y. Org. Biomol. Chem. 2009, 7, 3168. |
| [27] | Ullah, A.; Zhang, S.; Bao, M. Chin. J. Org. Chem. 2017, 37, 1278. |
| [28] | Harrod, J. F.; Chalk, A. J. Nature 1965, 205, 280. |
| [29] | Canovese, L.; Santo, C.; Visentin, F. Organometallics 2008, 27, 3577. |
| [30] | Tan, E. H. P.; Lloyd-Jones, G. C.; Harvey, J. N.; Lennox, A. J. J.; Mills, B. M. Angew. Chem.,Int. Ed. 2011, 50, 9602. |
| [31] | Giles, R. G. F.; Son, V. R. L.; Sargent, M. V. Aust. J. Chem. 1990, 43, 777. |
| [32] | Yu, J.; Gaunt, M. J.; Spencer, J. B. J. Org. Chem. 2002, 67, 4627. |
| [33] | Kim, I. S.; Zee, O. P.; Jung, Y. H. Org. Lett. 2006, 8, 4101. |
| [34] | Kim, I. S.; Dong, G. R.; Jung, Y. H. J. Org. Chem. 2007, 72, 5424. |
| [35] | Gauthier, D.; Lindhardt, A. T.; Olsen, E. P. K.; Overgaard, J.; Skrydstrup, T. J. Am. Chem. Soc. 2010, 132, 7998. |
| [36] | (a) Bai, X. F.; Xu, L. W.; Zheng, L. S.; Jiang, J. X.; Lai, G. Q.; Shang, J. Y. Chem.-Eur. J. 2012, 18, 8174. |
| [36] | (b) Xu, L. W.; Chen, X. H.; Shen, H.; Deng, Y.; Jiang, J. X.; Jiang, K. Z.; Lai, G. Q.; Sheng, C. Q. Eur. J. Org. Chem. 2012, 290. |
| [37] | Ohmura, T.; Oshima, K.; Suginome, M. Chem. Commun. 2008, 1416. |
| [38] | Albéniz, A. C.; Espinet, P.; Lin, Y. S. Organometallics 1996, 15, 5010. |
| [39] | Mirza-Aghayan, M.; Boukherroub, R.; Bolourtchian, M.; Ho-seini, M.; Tabar-Hydar, K. J. Organomet. Chem. 2003, 678, 1. |
| [40] | (a) Tkach, V. S.; Suslov, D. S.; Gomboogiin, M.; Ratovskii, G. V.; Shmidt, F. K. Russ. J. Appl. Chem. (Engl. Transl.) 2006, 79, 85. |
| [40] | (b) Gomboo, M.; Tkach, V. S.; Shmidt, F. K. React. Kinet. Catal. Lett. 2004, 83, 337. |
| [41] | Nishiwaki, N.; Kamimura, R.; Shono, K.; Kawakami, T.; Na-kayama, K.; Nishino, K.; Nakayama, T.; Takahashi, K.; Nakamura, A.; Hosokawa, T. Tetrahedron Lett. 2010, 51, 3590. |
| [42] | Jung, M. E.; Lee, G. S.; Pham, H. V.; Houk, K. N. Org. Lett. 2014, 16, 2382. |
| [43] | Chuc, L. T. N.; Chen, C. S.; Lo, W. S.; Shen, P.-C.; Hsuan, Y. C.; Gavin Tsai, H. H.; Shieh, F. K.; Hou, D. R. ACS Omega 2017, 2, 698. |
| [44] | Murai, M.; Nishimura, K.; Takai, K. Chem. Commun. 2019, 55, 2769. |
| [45] | Spallek, M. J.; Stockinger, S.; Goddard, R.; Trapp, O. Adv. Synth. Catal. 2012, 354, 1466. |
| [46] | Winston, M. S.; Oblad, P. F.; Labinger, J. A.; Bercaw, J. E. Angew. Chem., nt. Ed. 2012, 51, 9822. |
| [47] | Kocen, A. L.; Klimovica, K.; Brookhart, M.; Daugulis, O. Organometallics 2017, 36, 787. |
| [48] | Kocen, A. L.; Brookhart, M.; Daugulis, O. Chem. Commun. 2017, 53, 10010. |
| [49] | Yamasaki, Y.; Kumagai, T.; Kanno, S.; Kakiuchi, F.; Kochi, T. J. Org. Chem. 2018, 83, 9322. |
| [50] | Portnoy, M.; Milstein, D. Organometallics 1994, 13, 600. |
| [51] | Perez, P. J.; Calabrese, J. C.; Bunel, E. E. Organometallics 2001, 20, 337. |
| [52] | Sui-Seng, C.; Groux, L. F.; Zargarian, D. Organometallics 2006, 25, 571. |
| [53] | RajanBabu, T. V. Chem. Rev. 2003, 103, 2845. |
| [54] | Lim, H. J.; Smith, C. R.; RajanBabu, T. V. J. Org. Chem. 2009, 74, 4565. |
| [55] | (a) Barrios-Landeros, F.; Carrow, B. P.; Hartwig, J. F. J. Am. Chem. Soc. 2008, 130, 5842. |
| [55] | (b) Mamone, P.; Grünberg, M. F.; Fromm, A.; Khan, B. A.; Gooßen, L. J. Org. Lett. 2012, 14, 3716. |
| [55] | (c) Ohlmann, D. M.; Tschauder, N.; Stockis, J.-P.; Gooßen, K.; Dierker, M.; Gooßen, L. J. J. Am. Chem. Soc. 2012, 134, 13716. |
| [56] | Bai, X.-F.; Song, T.; Deng, W.-H.; Wei, Y.-L.; Li, L.; Xia, C.-G.; Xu, L.-W. Synlett 2014, 25, 417. |
| [57] | Ahn, H.; Son, I.; Lee, J.; Lim, H. J. Asian J. Org. Chem. 2017, 6, 335. |
| [58] | Ojha, D. P.; Gadde, K.; Prabhu, K. R. J. Org. Chem. 2017, 82, 4859. |
| [59] | Ren, W. L.; Sun, F.; Chu, J. X.; Shi, Y. A. Org. Lett. 2020, 22, 1868. |
| [60] | Ohmura, T.; Oshima, K.; Suginome, M. Angew. Chem., nt. Ed. 2011, 50, 12501. |
| [61] | Danishefsky, S.; O’Neill, B. T.; Taniyama, E.; Vaughan, K. Tetrahedron Lett. 1984, 25, 4199. |
| [62] | Schuppe, A. W.; Newhouse, T. R. J. Am. Chem. Soc. 2017, 139, 631. |
| [63] | Sánchez-Eleuterio, A.; Mastranzo, V. M.; Quintero, L.; Sartillo- Piscil, F. Lett. Org. Chem. 2017, 14, 261. |
| [64] | Sasaki, M.; Maruyama, T.; Sakai, R.; Tachibana, K. Tetrahedron Lett. 1999, 40, 3195. |
| [65] | (a) Campbell, A. D.; Tomasi, S.; Tiberghien, A. C.; Parker, J. S. Org. Process Res. Dev. 2019, 23, 2543. |
| [65] | (b) Tiberghien, A. C.; Levy, J.-N.; Masterson, L. A.; Patel, N. V.; Adams, L. R.; Corbett, S.; Williams, D. G.; Hartley, J. A.; Howard, P. W. ACS Med. Chem. Lett. 2016, 7, 983. |
/
| 〈 |
|
〉 |
