Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (1): 341-347.DOI: 10.6023/cjoc202006062 Previous Articles Next Articles
Article
夏艳萍a, 欧阳露a, 廖建华a, 魏一飞a, 罗人仕a,*()
收稿日期:
2020-06-29
修回日期:
2020-07-30
发布日期:
2020-08-27
通讯作者:
罗人仕
作者简介:
基金资助:
Yanping Xiaa, Lu Ouyanga, Jianhua Liaoa, Yifei Weia, Renshi Luoa,*()
Received:
2020-06-29
Revised:
2020-07-30
Published:
2020-08-27
Contact:
Renshi Luo
Supported by:
Share
Yanping Xia, Lu Ouyang, Jianhua Liao, Yifei Wei, Renshi Luo. Manganese-Mediated Reformatsky Reaction: Highly Divergent Synthesis ofβ-Hydroxyalkanoates[J]. Chinese Journal of Organic Chemistry, 2021, 41(1): 341-347.
Entry | X | [Ni] | Solvent | Time/h | Yield b /% of 3a |
---|---|---|---|---|---|
1 | Br | — | THF | 36 | 12 |
2 | I | — | THF | 36 | 25 |
3 | Br | NiBr 2 | THF | 36 | 27 |
4 c | Br | NiBr 2 | THF | 36 | 90 |
5 | I | NiBr 2 | THF | 36 | 94 |
6 | I | NiCl 2 | THF | 36 | 23 |
7 | I | NiI 2 | THF | 36 | 92 |
8 d | I | NiI 2 | THF | 12 | 92 |
9 d | I | NiI 2 | Et 2O | 12 | 93 |
10 d | I | NiI 2 | Dioxane | 12 | 90 |
11 d | I | NiI 2 | Toluene | 12 | 78 |
12 d | I | NiI 2 | DCM | 12 | 80 |
13 d | I | NiI 2 | Hexane | 12 | 85 |
14 d | I | NiI 2 | MeCN | 12 | 98 |
Entry | X | [Ni] | Solvent | Time/h | Yield b /% of 3a |
---|---|---|---|---|---|
1 | Br | — | THF | 36 | 12 |
2 | I | — | THF | 36 | 25 |
3 | Br | NiBr 2 | THF | 36 | 27 |
4 c | Br | NiBr 2 | THF | 36 | 90 |
5 | I | NiBr 2 | THF | 36 | 94 |
6 | I | NiCl 2 | THF | 36 | 23 |
7 | I | NiI 2 | THF | 36 | 92 |
8 d | I | NiI 2 | THF | 12 | 92 |
9 d | I | NiI 2 | Et 2O | 12 | 93 |
10 d | I | NiI 2 | Dioxane | 12 | 90 |
11 d | I | NiI 2 | Toluene | 12 | 78 |
12 d | I | NiI 2 | DCM | 12 | 80 |
13 d | I | NiI 2 | Hexane | 12 | 85 |
14 d | I | NiI 2 | MeCN | 12 | 98 |
[1] |
(a) Paterson I.; Chen D.Y.-K.; Coster M.J.; Aceña J.L.; Bach nJ.; Gibson K.R.L. E.; Oballa, R.M.; Trieselmann, T.; Wallace, D.J.; Hodgson, A.P.; Norcross, R.D. Angew. Chem., Int. Ed. 2001, 40, 4055.
|
(b) Calter, M. A.; W. Liao, J. Am. Chem. Soc. 2002, 124, 13127.
|
|
(c) Schetter, B.; R. Mahrwald, Angew. Chem., Int. Ed. . 2006, 45, 7506.
|
|
(d) List, B.; Lerner, R. A.; Barbas, C. F. J. Am. Chem. Soc. 2000, 122, 2395.
|
|
(e) Cheng-Sánchez, I.; Carrillo, P.; Sánchez-Ruiz, A.; Martínez-Poveda, B.; A. Quesada, R.; M. Medina, A.; J. López- Romero, M.; Sarabia, F. J. Org. Chem. 2018, 83, 5365.
|
|
(f) Kang, T.; Han, D. Jo, S. J. Org. Chem. 2017, 82, 9335.
|
|
(g) Gomez-Palomino, A.; Romea, P.; Urpí, F. Synthesis . 2018, 50, 2721.
|
|
[2] |
(a) Mandavid H.; Rodrigues A.M.S.; Espindola L.S.; Eparvier V.; Stien D.J. Nat. Prod. 201 5, 78, 1735.
|
(b) Nakamukai S.; Takada K.; Furihata K.; Ise Y.; Okada S.; Morii Y.; Yamawaki N.; Takatani T.; Arakawa O.; Gustafson K.R.; Stellatolide H Matsunaga, S.Tetrahedron Lett. 2018, 59, 2532.
|
|
(c) Shin H.J.; Rashid M.A.; Cartner L.K.; Bokesch H.R.; Wilson J.A.; McMahon J.B.; Gustafson K.R. Tetrahedron Lett. 2015, 56, 4215.
|
|
(d) Bae M.; Moon K.; Kim J.; Park H.J.; Lee S.K.; Shin J.; Oh D.-C. J. Nat. Prod. 2016, 79, 332.
|
|
[3] |
Reformatsky S. Ber. Dtsch. Chem. Ges. 1887, 20, 1210.
|
[4] |
(a) Choppin S.; Ferreiro-Medeiros L.; Barbarottoa M.; Colobert F. Chem. Soc. Rev. 2013, 42, 937.
|
(b) Kim J.H.; Ko Y.O.; Bouffard J.; Lee S. Chem. Soc. Rev. 2015, 44, 2489.
|
|
(c) Shen Z.-L.; Wang S.-Y.; Chok Y.-K.; Xu Y.-H.; Loh T.-P. Chem. Rev. 2013, 113, 271.
|
|
(d) Cozzi P.G. Angew. Chem. Int. Ed. 2007, 46, 2568.
|
|
[5] |
(a) Yamakoshi S.; Kawanishi E. Tetrahedron Lett. 2014, 55, 1175.
|
(b) Wu P.; Cai W.; Chen Q.-Y.; Xu S.; Yin R.; Li Y.; Zhang W.; Luesch H. Org. Lett. 2016, 18, 5400.
|
|
(c) Yun J.-J.; Zhi M.-L.; Shi W.-X.; Chu X.-Q.; Shen Z.-L.; Loh T.-P. Adv. Synth. Catal. 2018, 360, 2632.
|
|
(d) Liu X.-Y.; Li X.-R.; Zhang C.; Chu X.-Q.; Rao W.; Loh T.-P.; Shen Z.-L. Org. Lett. 2019, 21, 5873.
|
|
(e) Sinast M.; Zuccolo M.; Wischnat J.; Sube T.; Hasnik F.; Baro A.; Dallavalle S.; Laschat S. J. Org. Chem. 2019, 84, 10050.
|
|
(f) Cao Q.; Stark R.T.; Fallis I.A.; Browne D.L. ChemSusChem 2019, 12, 2554.
|
|
[6] |
Frstner A. Synthesis 1989, 571.
|
(b) Marshall J.A. Chemtracts 2000, 13, 705.
|
|
Podlech J.; Maier T.C. Synthesis 2003, 633.
|
|
(d) Orsini F.; Sello G. Curr. Org. Synth. 2004, 1, 111.
|
|
Nakamurai E. InOrganometallic in Synthesis, A Manual, Ed.: Schlosser, M., Wiley, New York, 2002, p. 579.
|
|
(f) Ocampo R.; Dolbier Jr, W.R. Tetrahedron 2004, 60, 9325.
|
|
[7] |
(a) Peng Y.-Y.; Liu P.; Liu Z.-J.; Liu J.-T.; Mao H.-F.; Yao Y.-L. Tetrahedron 2018, 74, 3074.
|
(b) Cao C.-R.; Jiang M.; Liu J.-T. Eur. J. Org. Chem. 2015, 1144.
|
|
(c) Huck L.; Berton M.; de la Hoz A.; Díaz-Ortizb A.; Alcázar J. Green Chem. 2017, 19, 1420.
|
|
(d) Fernández-Sánchez L.; Fernández-Salas J.A.; Maestro M.C.; García Ruano, J.L.J. Org. Chem. 2018, 83, 12903.
|
|
(e) De Munck, L.; Sukowski, V.; Vila, C.; Muñozb, M.C.; Pedro, J.R. Org. Chem. Front. 2017, 4, 1624.
|
|
[8] |
(a) Fernandez-Ibanez M.A.; Macia B.; Minnaard A.J.; Feringa B.L. Angew. Chem., Int. Ed. 2008, 47, 1317.
|
(b) Fornalczyk M.; Singh K.; Stuart A.M. Chem. Commun. 2012, 48, 3500.
|
|
(c) Maestro A.; de Marigorta E.M.; Palacios F.; Vicario J. Org. Lett. 2019, 21, 9473.
|
|
(d) DeβMunck L.; Vila C.; Muñoz M.C.; Pedro J.R. Chem. Eur. J. 2016, 22, 17590.
|
|
[9] |
(a) Chattopadhyay A.; Kr Dubey, A.J. Org. Chem. 2007, 72, 9357.
|
(b) Moriwake T. J. Org. Chem. 1966, 31, 983.
|
|
[10] |
(a) Orsini F.; Lucci E.M. Tetrahedron Lett. 2005, 46, 1909.
|
(b) Segade Y.; Montaos M.A.; Rodríguez J.; Jimenez C. Org. Lett. 2014, 16, 5820.
|
|
(c) Nelson C.G.; Jr. Burke, T.R.J. Org. Chem. 2012, 77, 733.
|
|
(d) Sinast M.; Zuccolo M.; Wischnat J.; Sube T.; Hasnik F.; Baro A.; Dallavalle S.; Laschat S. J. Org. Chem. 2019, 84, 10050.
|
|
[11] |
(a) Hu Y.; Zhou B.; Wang C. Acc. Chem. Res. 2018, 51, 816.
|
(b) Hammarback L.A.; Clark I.P.; Sazanovich I.V.; Towrie M.; Robinson A.; Clarke F.; Meyer S.; Fairlamb I.J.S.; Lynam J.M. Nat. Catal. 2018, 1, 830.
|
|
[12] |
(a) Cozzi P.G.; Rivalta E. Angew. Chem. Int. Ed. 2005, 44, 3600.
|
[13] |
(a) Cozzi P.G. Angew. Chem. Int. Ed. 2007, 46, 2568.
|
(b) Li R.; Xu H.; Zhao N.; Jin X.; Dang Y. J. Org. Chem. 2020, 85, 833.
|
|
[14] |
(a) Börjesson M.; Moragas T.; Gallego D.; Martin R. ACS Catal. 2016, 6, 6739.
|
(b) Börjesson M.; Moragas T.; Gallego D.; Martin R. J. Am. Chem. Soc. 2016, 138, 7504.
|
|
[15] |
Zoua X.-L.; Dua G.-F.; Sun W.-F.; He L.; Ma X.-W.; Gu C.-Z.; Dai B. Tetrahedron 2013, 69, 607.
|
[16] |
Baudoux J.; Lefebvre P.; Legay R.; Lasne M.-C.; Rouden J. Green Chem. 2010, 12, 252.
|
[17] |
Wadhwa K.; Verkade J.G. J. Org. Chem. 2009, 74, 4368.
|
[1] | Xiaoyu Zhang, Xinyan Li, Bing Cui, Zhihui Shao, Mingqin Zhao. Design, Synthesis and Antioxidant Activity of Tetrahydro-β-carbolines [J]. Chinese Journal of Organic Chemistry, 2023, 43(8): 2885-2894. |
[2] | Guijie Liu, Zhengqiang Fu, Fei Chen, Caixia Xu, Min Li, Ning Liu. N-Heterocyclic Carbene-Pyridine Manganese Complex/ Tetrabutylammonium Iodide Catalyzed Synthesis of Cyclic Carbonate from CO2 and Epoxide [J]. Chinese Journal of Organic Chemistry, 2023, 43(2): 629-635. |
[3] | Yudong Li, Ying Li, Ya'nan Dong, Chungu Xia, Yuehui Li. Manganese-Catalyzed Allylation of Quinazolinones with 4-Vinyl-1,3-dioxolan-2-one via C—H Activation [J]. Chinese Journal of Organic Chemistry, 2022, 42(3): 847-853. |
[4] | Lü Jinqiang, Zeng Jing, Abulikemu Abudu Rexit. Highly Active Manganese Dioxide Catalyzed the Construction of S-S Bond [J]. Chinese Journal of Organic Chemistry, 2020, 40(8): 2483-2490. |
[5] | Liu Tianbao, Peng Na, Wang Panpan, Peng Yanfen, Gui Meifang, Zhang Min. A New Method for Synthesis of Naphtho[2,1-d]thiazole Derivatives [J]. Chinese Journal of Organic Chemistry, 2020, 40(5): 1355-1360. |
[6] | Chen Zhen, Guo Kang, Chen Rongshun, Gu Chen, Zhou Huating, Zhu Yingguang. Facile Access to β-Ketosulfones via Mn-Mediated Reductive Coupling of α-Bromoketones with Sulfonyl Chlorides [J]. Chin. J. Org. Chem., 2018, 38(4): 963-968. |
[7] | Hu Xinyu, Yang Bobin, Yao Wei, Wang Dawei. Alanine Triazole Mn-Catalyzed Coupling/Aromatization of Quinone Methides [J]. Chin. J. Org. Chem., 2018, 38(12): 3296-3301. |
[8] | Yang Jinchuang, Li Guosong, Lü Chengwei, An Yue, Gao Shuang. Oxidation Kinetics Resolution of Racemic Aromatic Sulfoxides by Chiral Porphyrin-Inspired N4 Ligand with Manganese Complex [J]. Chin. J. Org. Chem., 2018, 38(11): 3070-3077. |
[9] | Chang Yi, Liu Mengyang, Niu Mengyuan. Efficient Synthesis of Anionic and Cationic Water-Soluble Porphyrins [J]. Chin. J. Org. Chem., 2017, 37(9): 2442-2448. |
[10] | Zou Xiaochuan, Shi Kaiyun, Li Jun, Wang Yue, Wang Cun, Deng Chaofang, Ren Yanrong, Tan Jun, Fu Xiangkai. Research Progress on Epoxidation of Olefins Catalyzed by Mn(II, III, V) in Different Valence States [J]. Chin. J. Org. Chem., 2016, 36(8): 1765-1778. |
[11] | YU Fu-Chao, YAN Sheng-Jiao, HE Neng-Qin, LIN Jun. Synthesis of 2-Diethyl Phosphate Heterocyclic Ketene Aminals [J]. Chin. J. Org. Chem., 2011, 31(9): 1504-1509. |
[12] | LIU Chang-Chun, YUAN Jia-Cheng, TAN Pei-Yi, JIN De-Kuan. Reformatsky Reaction Promoted by [bmim]Cl-CrCl2 Ionic Liquid [J]. Chin. J. Org. Chem., 2009, 29(10): 1650-1653. |
[13] | LIU Feng-Liang*,a,LI Yuan-Jianb,HUANG Ke-Longa,YANG Wei-Junc. Synthesis, Oxygenation and Catalytic Behavior of Manganese Complex with Bis(2-hydroxyphenyliminomethyl) [J]. Chin. J. Org. Chem., 2007, 27(9): 1106-1109. |
[14] | PEI Wen*, SHEN Chen, MO Jun, XU Xiao-Liang. Synthesis of 2-Substituted Naphthyl Allyl Alcohols byHeck Re-action in Ionic Liquids [J]. Chin. J. Org. Chem., 2007, 27(05): 653-655. |
[15] | DENG Gui-Sheng*,XU Bai-Hua,LIU Chun-Yu. One-Pot Synthesis of α,β-Unsaturated Esters from Silyl Ethers by Means of in situ Deprotection-Oxidation-Wittig Re-action [J]. Chin. J. Org. Chem., 2006, 26(9): 1295-1299. |
Viewed | ||||||
Full text |
|
|||||
Abstract |
|
|||||