Manganese-Mediated Reformatsky Reaction: Highly Divergent Synthesis ofβ-Hydroxyalkanoates

doi:10.6023/cjoc202006062

Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (1): 341-347.DOI: 10.6023/cjoc202006062 Previous Articles Next Articles

Article

锰介导的Reformatsky反应: 高效合成多样化 β-羟基链烷酸酯

夏艳萍^a, 欧阳露^a, 廖建华^a, 魏一飞^a, 罗人仕^a^,^*()

a 赣南医学院药学院江西赣州 341000

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:
* Corresponding author. E-mail: luorenshi2010@163.com
基金资助:
国家自然科学基金(21962004); 国家自然科学基金(21562004); 江西省自然科学基金(20192BAB203004); 赣南医学院(QD201810); 赣南医学院(YJ202027)

Manganese-Mediated Reformatsky Reaction: Highly Divergent Synthesis ofβ-Hydroxyalkanoates

Yanping Xia^a, Lu Ouyang^a, Jianhua Liao^a, Yifei Wei^a, Renshi Luo^a^,^*()

a School of Pharmacy, Gannan Medical University, Ganzhou, Jiangxi 341000

Received:2020-06-29 Revised:2020-07-30 Published:2020-08-27
Contact: Renshi Luo
Supported by:
the the National Natural Science Foundation of China(21962004); the the National Natural Science Foundation of China(21562004); Jiangxi provincial department of science and technology(20192BAB203004); Gannan Medical University(QD201810); Gannan Medical University(YJ202027)

1. cjoc202006062辅助材料.pdf(5403KB)

Abstract

A practical, flexible, and efficient manganese-mediated catalytic system of Reformatsky reaction has been described. The cheap and readily available manganese powder acts as the reaction mediator, which conducts effectively for the preparation of useful β-hydroxyalkanoate compounds with the nickel catalyst in excellent yields (up to 98%) and mild condition. In addition, the catalytic methodology can be scaled up to the gram scale.

Key words: manganese, nickel catalyst, reformatsky, aldehydes and ketones, β-hydroxyalkanoates

Cite this article

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.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

Fig. & Tab. 7

References 17

[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.

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

锰介导的Reformatsky反应: 高效合成多样化 β-羟基链烷酸酯

Manganese-Mediated Reformatsky Reaction: Highly Divergent Synthesis ofβ-Hydroxyalkanoates

RichHTML

PDF

Supporting Info.

Knowledge

Abstract

Cite this article

share this article

Fig. & Tab. 7

References 17

Related Articles 15

Recommended Articles

Metrics

Comments

[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-Jian^b,HUANG Ke-Long^a,YANG Wei-Jun^c. 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.