Chinese Journal of Organic Chemistry
REWIEW
冯凯a, 贺兆波*,a, 王震*,a,b
收稿日期:2025-09-28
修回日期:2025-11-28
Feng, Kaia, He, ZhaoBo*,a, Wang, Zhen*,a,b
Received:2025-09-28
Revised:2025-11-28
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Feng, Kai, He, ZhaoBo, Wang, Zhen. Recent Advances in Palladium-Catalyzed Asymmetric Hydroesterification of Alkenes[J]. Chinese Journal of Organic Chemistry, doi: 10.6023/cjoc202509035.
| [1] (a) Moen M.D.; Keam, S.J.CNS Drugs2009, 23, 1057. (b) Butler A.R.; Wu, Y.-L.Chem.Soc.Rev.1992, 21, 85. (c) Xia J.Y.; Yang D.Q.; Long, Y.H.Chin.J.Org.Chem.2011, 31, 593 (in Chinese). (夏九云, 杨定乔, 龙玉华,有机化学, 2011, 31, 593). (d) Wang J.G.; Xu C.C.; Wong Y.K.; Li Y.J.; Liao F.L.; Jiang T.L.; Tu Y.Y.Engineering2019, 5, 32. (e) Halama A.; Zapadlo, M.Org.Process Res.Dev.2019, 23, 102. (f) Ma K.Q.; Martin B.S.; Yin X.L.; Dai, M.J.Nat.Prod.Rep.2019, 36, 174. (g) Iacoviello M.; Palazzuoli A.; Gronda, E. Eur.J.Clin.Invest.2021, 51, e13624. (h) Li J.H.; Shi, Y.A.Chem.Soc.Rev.2022, 51, 6757. (i) Kuai, C -S.; Wang Y.R.; Yang T.; Wu, X -F.J.Am.Chem.Soc.2025, 147, 7950. [2] (a) Yang, H.; Tang, W.J.Chem.Rec.2020, 20, 23. (b) Mas-Roselló J.; Herraiz A.G.; Audic B.; Laverny A.; Cramer, N.Angew.Chem.Int.Ed.2021, 60, 13198. (c) Margalef J.; Biosca M.; de la Cruz Sánchez, P.; Faiges J.; Pàmies O.; Diéguez, M.Coord.Chem.Rev.2021, 446, 214120. (d) Wang, H.; Wen, J.L.; Zhang, X.M. Chem.Rev.2021, 121, 7530. [3] (a) Knowles W.S.; Sabacky, M.J.J.Chem.Soc., Chem.Commun.1968, 20, 1445. (b) Horner L.; Sieged H.; Buthe, H.Angew.Chem.Int.Ed.1968, 7, 942. (c) Ni H.Z.; Chan W.-L.; Lu, Y.X.Chem.Rev.2018, 118, 9344. (d) Xu G.Q.; Senanayake C.H.; Tang, W.J.Acc.Chem.Res.2019, 52,1101. (e) Imamoto, T. Proc.Jpn.Acad., Ser.B 2021, 97, 520. (f) Stephan M.; Jeran M.; Mohar, B. Org.Process Res.Dev.2024, 28, 11. (g) Chen W.; Cai P.; Zhou H.C.; Madrahimov, S.T.Angew.Chem.Int.Ed.2024, 63, e202315075. (h) Su, L.; Gao, S.; Liu, J.W.Nat.Commun.2024, 15, 7248. (i) Ye B.H.; Su L.; Zheng K.T.; Gao S.; Liu, J.W.Angew.Chem.Int.Ed.2025, 64, e202413949. [4] (a) Zhou, Y.R.; Gong, Y.F.Eur.J.Org.Chem.2011, 6092. (b) Shen X.Z.; Chen X.; Chen J.P.; Sun Y.F.; Cheng Z.Y.; Lu Z.Nat.Commun.2020, 11, 783. (c) Liu,W.; Jiang Q.W.; Yang, X.Y.Angew.Chem.Int.Ed.2020, 59, 23598. (d) Wu, X Q.; Turlik A.T.; Luan B.X.; He F.; Qu J.P.; Houk K.N.; Chen.Y.F.Angew.Chem.Int.Ed.2022, 61, e202207536. (e) Wu, X Q.; Qu J.P.; Chen.Y.F.J.Am.Chem.Soc.2020, 142, 15654. (f) Wu, X Q.; Li H.Y.; He F.; Qu J.P.; Chen.Y.F.Chin.J.Chem.2023, 41, 1673. (g) Jin L.; Li Y.; Mao Y.H.; He X.-B.; Lu Z.; Zhang Q.; Shi B.-F.Nat.Commun.2024, 15, 4908. (h) Cui B.; Zheng Y.T.; Sun H.; Shang H.J.; Du M.; Shang Y.X.; Yavuz, C.T.Nat.Commun.2024, 15, 6647. [5] (a) Hiroi K.; Sone, T.Curr.Org.Synth.2008, 5, 305. (b) Liu Z.Q.; Feng X.Q.; Du, H.F.Org.Lett.2012, 14, 3154. (c) Trost B.M.; Rao, M.Angew.Chem.Int.Ed.2015, 54, 5026. (d) Otocka S.; Kwiatkowska M.; Madalinska L.; Kiełbasiński P.Chem.Rev.2017, 117,4147. (e) Li X.; Zheng S.-C.; Zhao, X.-M.Eur.J.Org.Chem.2025, 28, e202401172. [6] (a) Su B.; Zhou T.-G.; Xu P.-L.; Shi Z.-J.; Hartwig, J.F.Angew.Chem.Int.Ed.2017, 56,7205. (b) Babu K .N.; Kinthada L.K.; Das P.P.; Bisai A.Chem.Commun.2018, 54, 7963. (c) Zhang S.T.; Wu S.J.; Wang Q.; Xu S.J.; Han Y.; Yan C.-G.; Zhang J.L.; Wang, L.Angew.Chem.Int.Ed.2023, 62, e202300309. (d) Tu Y.S.; Xu B.; Wang Q.; Dong H.L.; Zhang Z.-M.; Zhang, J.L.J.Am.Chem.Soc.2023, 145, 4378. (e) Liao G.; Shi, B,-F. Acc.Chem.Res.2025, 58, 1562. (f) Yan Xu.; Feng W.; Ng J.X.; Li J.X.; Liu Y.; Zhang B.; Shao P.-L.; Zhao, Y.Chem.Soc.Rev.2025, Advance Article. [7] (a) Lin, G.-Q.; Li, Y.-M.; Chan, A.S.C.Wiley, New York, 2001. (b) Xie J.-H.; Zhou, Q.-L.Acta Chim.Sinica2012, 70, 1427. (c) Zhao, W.X.; Yang, D.Y.; Zhang, Y.H.Chin.J.Org.Chem.2016, 36, 2301. [8] (a) Yu X.H.; Wang, W.Chem.Asian J.2008, 3, 516. (b) Lyubimov S.E.; Kalinin V.N.; Tyutyunov A.A.; Olshevskaya V.A.; Dutikova Y.V.; Cheong C.S.; Petrovskii P.V.; Safronov A.S.; Davankov V.A.Chirality2009, 21, 2. (c) Luo J.; Zhang T.; Wang L.; Liao G.; Yao Q.J.; Wu Y.J.; Zhan B.B.; Lan Y.; Lin X.F.; Shi, B.F.Angew.Chem.Int.Ed.2019, 58, 6708. (d) Liu X.-R.; Cui, P -F.; Guo S.-T.; Lin Y.-J.; Jin, G.-X.J.Am.Chem.Soc.2021, 143, 5099. (e) Li P.P.; Zheng E.; Li G.L.; Luo Y.C.; Huo X.H.; Ma S.M.; Zhang W.B.Science2024, 385, 972. [9] (a) Ren X.Y.; Wang Z.; Shen C.R.; Tian X.X.; Tang L.; Ji X.L.; Dong, K.W.Angew.Chem.Int.Ed.2021, 60,17693. (b) Wang, Z.; Shen, C.R.; Dong, K.W.Angew.Chem.Int.Ed.2024, e202410967. (c) Wang Z.; Dong, K.W.Chin.J.Org.Chem.2024, 44, 3249 (in Chinese). (王震, 董开武, 有机化学, 2024, 44, 3249). [10] (a) Clegg, W.; Elsegood, M.R.J.; Eastham, G.R.; Tooze, R.P.; Wang, X.L.; Whiston, K.Chem.Commun.1999, 1877. (b) Kiss, G.Chem.Rev. 2001, 101, 3435. (c) del Rıo I.; Ruiz N.; Claver, C.Inorg. Chem.Commun.2000, 3, 166. (d) Godard, C.; Muñoz, B.K.; Ruiz.A.; Claver, C.Dalton Trans.2008, 853. [11] (a) Xu Z.S.; Shen C.R.; Zhang H.R.; Wang P.; Dong, K.W.Org.Chem.Front.2021, 8, 1163. (b) Peng J.-B.; Liu X.-L.; Li L.; Wu, X.-F.Sci.China: Chem.2022, 65, 441. (c) Cheng S.D.; Luo Y.; Yu T.; Li J.; Gan C.F.; Luo S.; Zhu Q.ACS Catal.2022, 12, 837. (d) Shen C.R.; Dong K.W.Synlett2022, 33, 815. [12] (a) Botteghi C.; Consiglio G.; Pino P.Chimia1973, 27, 477. (b) Consiglio G.; Pino P.Chimia1976, 30, 193. (c) Consiglio, G.Helv.Chim.Acta. 1976, 59, 124. (d) Consiglio, G.J.Organomet.Chem. 1977, 132, C26. [13] Hayashi T.; Tanaka M.; Ogata I.Tetrahedron Lett.1978, 41, 3925. [14] Cometti G.; Chiusoli, G.P.J.Organomet.Chem.1982, 236, C31. [15] Zhou H.Y.; Hou J.G.; Cheng J.; Lu S.J.; Fu.H.X.; Wang, H.Q.J.Organomet.Chem.1997, 543, 227. [16] Oi S.; Nomura M.; Aiko T.; Inoue, Y.J.Mol.Catal.A: Chem.1997, 115, 289. [17] Beller M.; Comils B.; Frohning C.D.; Kohlpaintner, C.W.J.Mol.Catal.A: Chem.1995, 104, 17. [18] Nozaki K.; Kantam M.L.; Horiuchi T.; Takaya, H.J.Mol.Catal.A: Chem.1997, 118, 247. [19] Wang L.L.; Kwok W.H.; Chan A.S.; Tu T.; Hou, X.L; Dai, L.X. Tetrahedron: Asymmetry 2003, 14, 2291. [20] Kawashima Y.; Okano K.; Nozaki K.; Hiyama, T.Bull.Chem.Soc.Jpn.2004, 77, 347. [21] Muñoz.B.K.; Marinetti A.; Ruiz A.; Castillon S.; Claver, C.Inorg.Chem.Commun.2005, 8, 1113. [22] Marinetti A.; Kruger V.; Buzin, F.-X.Coord.Chem.Rev.1998, 178-180, 755. [23] Muñoz B.K.; Godard C.; Marinetti A.; Ruiz A.; Benet-Buchholz J.; Claver C.Dalton Trans.2007, 47, 5524. [24] Godard C.; Ruiz A.; Claver.C.Helv.Chimica Acta 2006, 89, 1610. [25] Guiu E.; Caporali M.; Munoz B.; Müller C.; Lutz M.; Spek A.L.; van Leeuwen, P.W.Organometallics 2006, 25, 3102. [26] Yao Y.-H.; Zou X.-J.; Wang Y.; Yang H.-Y.; Ren, Z.-H; Guan Z.-H.Angew.Chem.Int.Ed.2021, 60, 23117. [27] Chelucci G.; Cabras M.A.; Botteghi C.; Chelucci M.Tetrahedron: Asymmetry1994, 5, 299. [28] Konrad T.M.; Fuentes J.A.; Slawin A.M.Z.; Clarke, M.L.Angew.Chem.Int.Ed.2010, 49, 9197. [29] Konrad T.M.; Durrani J.T.; Cobley C.J.; Clarke, M.L.Chem.Commun.2013, 49, 3306. [30] Gallarati S.; Dingwall P.; Fuentes J.A.; Bühl M.; Clarke M.L.Organometallics2020, 39, 4544. [31] Harkness G.J.; Clarke M.L.Eur.J.Org.Chem.2017, 4859. [32] Li J.F.; Chang W.J.; Ren W.L.; Dai J.; Shi Y.A.Org.Lett.2016, 18, 5456. [33] Li J.F.; Ren W.L.; Dai J.; Shi, Y.A.Org.Chem.Front.2018, 5, 75. [34] Pongrácz P.; Seni A.A.; L.T.; Kollár L.Mol.Catal.2017, 438, 15. [35] Ji X.L.; Shen C.R.; Tian X.X.; Dong, K.W.Org.Lett.2021, 23, 8645. [36] Zhou H.Y.; Lu S.J.; Hou J.G.; Chen J.; Fu H.X.; Wang H,Q.Chem.Lett.1996, 339. [37] Blanco C.; Ruiz A.; Godard C.; Fleury-Bregeot N.; Marinetti A.; Claver, C.Adv.Synth.Catal.,2009, 351,1813. [38] Andrieu J.; Braunstein P.; Naud F.; Adams, R.D.J.Organomet.Chem.2000, 601, 43. [39] Fuentes J A.; Durrani J T.; Leckie S M.; Crawford L.; Bühl M.; Clarke M.L.Catal.Sci.Technol.2016, 6, 7477. [40] (a) Castarlenas R.;Di Giuseppe A.; Pérez-Torrente J.J.; Oro, L.A.Angew.Chem.Int.Ed.2013, 52, 211. (b) Ai, H J.; Lu W.Y.; Wu, X.-F.Angew.Chem.Int.Ed.2021, 60, 17178. (c) Wang L.-C.; Wu X.-F.Nat.Commun.2025, 16, 4663. [41] Xiao W.-J.; Alper, H.J.Org.Chem.2001, 66, 6229. [42] Wang X.H.; Wang B.; Yin X.M.; Yu W.A.; Liao Y.; Ye J.L.; Wang M.; Hu L.R.; Liao, J.Angew.Chem.Int.Ed.2019, 58, 12264. [43] Alper H.; Hamel N.J.Chem.Soc., Chem.Commun.1990, 135. [44] Yu W.-Y.; Bensimon C.; Alper, H.Chem.Eur.J.1997, 3, 417. [45] Cao P.; Zhang, X.M.J.Am.Chem.Soc.1999, 121, 7708. [46] Shi Z.L.; Shen C.R.; Dong, K.W.Chem.Eur.J.2021, 27, 18039. [47] Dong C.; Alper, H.J.Org.Chem.2004, 69, 5011. [48] Wang, H.N; Dong, B.; Wang Y.; Li J.F.; Shi, Y.A.Org.Lett.2014, 16, 186. [49] Li J.F.; Chang W.J.; Ren W.L.; Liu W.; Wang H.N.; Shi, Y.A.Org.Biomol.Chem.2015, 13, 10341. [50] Tian D.S.; Xu R.H.; Zhu J.B.; Huang J.X.; Dong W.; Claverie J.; Tang, W.J.Angew.Chem.Int.Ed.2021, 60, 6305. [51] Alper H.; Hamel, N.J.Am.Chem.Soc.1990, 112, 2803. [52] Jiang B.; Huang Z.-G.;Cheng K.-J.Heterocycles2004, 63, 2797. [53] Miquel-Serrano M.D.; Aghmiz A.; Die´guez M.; Masdeu-Bulto´ A.M.; Claver C.; Sinou D.Tetrahedron: Asymmetry1999, 10, 4463. [54] Huang Z.J.; Cheng Y.Z.; Chen X.P.; Wang H.-F.; Du C.-X.; Li, Y.H.Chem.Commun.2018, 54, 3967. [55] Ji X.L.; Shen, C.R., Tian, X.X.; Zhang H.R.; Ren X.Y.; Dong, K.W.Angew.Chem.Int.Ed.2022, 61, e202204156. [56] Marcos-Ayuso G.; Quesada D.; Cobos-Abad M.Y.; Lendínez C.; Fernández-Moyano S.; Mauleón P.; Arrayás, R.G.ACS Catal.2025, 15, 20230. |
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