Electrochemical Synthesis of Homoallylic Alcohols and Homoallylic Amines

Authors

Wei-qiang ZHONG, Key Laboratory of Functional Molecular Engineering of Guangdong Province, School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou, Guangdong 510641, China;
Xiang-hui LIANG, Key Laboratory of Functional Molecular Engineering of Guangdong Province, School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou, Guangdong 510641, China;
Jing-mei HUANG, Key Laboratory of Functional Molecular Engineering of Guangdong Province, School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou, Guangdong 510641, China;Follow

Corresponding Author

Jing-mei HUANG(chehjm@scut.edu.cn)

Abstract

Electrochemical technique has been widely applied in the organic synthesis. This review focuses on the electrochemical synthesis of homoallylic alcohols and homoallylic amines from the allylation of carbonyl compounds and imines. This method has been developed impressively, especially in the field of electrochemical allylation in a green solvent of aqueous media. Improvement of the efficiency of the electricity, regio-selectivity and chiral synthesis are expected.

Graphical Abstract

Keywords

Eletrochemical synthesis, Homoallylic alcohols, Homoallylic amines, Allylation

DOI Link

https://doi.org/10.13208/j.electrochem.161047

Publication Date

2017-06-29

Online Available Date

2017-01-19

Revised Date

2017-01-16

Received Date

2016-10-31

Recommended Citation

Wei-qiang ZHONG, Xiang-hui LIANG, Jing-mei HUANG. Electrochemical Synthesis of Homoallylic Alcohols and Homoallylic Amines[J]. Journal of Electrochemistry, 2017 , 23(3): 297-306.
DOI: 10.13208/j.electrochem.161047
Available at: https://jelectrochem.xmu.edu.cn/journal/vol23/iss3/5

References

[1] Yamamoto Y, Asao N. Selective reactions using allylic metals[J]. Chem. Rev., 1993, 93(6), 2207-2293.

[2] (a) Yoshida J, Kataoka K, Horcajada R, Nagaki A. Modern Strategies in Electroorganic Synthesis[J]. Chem. Rev., 2008, 108(7), 2265-2299. (b) Little R D, Moeller K D. Organic electrochemistry as a tool for synthesis. Umpolung reactions, reactive intermediates, and the design of new synthetic methods[J]. Electrochem. Soc. Interf, 2002, 11(4), 36-42. (c) Moeller K D. Synthetic Applications of Anodic Electrochemistry[J]. Tetrahedron, 2000, 56(49), 9527-9554. (d) Frontana-Uribe B A, Little R D, Ibanez J G, et al. Organic Electrosynthesis: a promising green methodology in organic chemistry[J]. Green Chem., 2010, 12(12), 2099-2119. (e) Anastas P T, Kirchhoff M M Acc. Origins, Current status, and Future Challenges of Green Chemistry[J]. Chem. Res., 2002, 35(9), 686-694.

[3] Satoh S, Suginome H, Tokuda M. Regioselectivity in electrochemical additions of the allyl groups in substituted allyl halides to α,β-unsaturated esters or acetone[J]. Tetrahedron Lett., 1981, 22(20), 1895-1898.

[4] Tokuda M, Satoh S, Suginome H. Regioselectivity in electrochemical allylation of carbonyl compounds. A synthesis of egomaketone by regioselective allylation[J]. J. Org. Chem., 1989, 54(23), 5608-5613.

[5] Tokuda M, Uchida M, Katoh Y. et al. New efficient electrochemical allylation of aldehydes and ketones with a cadmium-modified electrode[J]. Chem.Lett., 1990, 461-462.

[6] Uneyama K, Matsuda H, Torri S. Grignard-type allylation of carbonyl compounds in methanol by the electrochemically recycled allyltin reagent[J]. Tetrahedron Lett., 1984, 25(52), 6017-6020.

[7] Sibille S, d€™Incan E, Leport. L. Electroreductive coupling of methallylchloride or methyl chloroacetate with carbonyl compounds catalyzed by nickel bipyridine complexes[J]. Tetrahedron Lett., 1987, 28(1), 55-58.

[8] Hilt G, Smoko K. I. Electrochemical Regeneration of Low-Valent Indium(I) Species as Catalysts for C-C Bond Formations[J]. Angew. Chem. Int. Ed. 2001, 40(18), 3399-3402.

[9] Amemiya F, Fuse K, Fuchigami T and Atobe M. Chemoselective reaction system using a two inlet micro-flow reactor: application to carbonyl allylation[J]. Chem. Commun.,2010, 46(16), 2730€“2732.

[10] Ronny F M S, Madalena C C A, Lothar W B, et al. Electrochemical allylation of aldehydes in a solvent-free cavity cell with a graphite powder cathode[J]. Green Chem., 2011, 13(5), 1118€“1120.

[11] Sahloul K, Sun L H, Requet A, et al. A Samarium €œSoluble€ Anode: A New Source of SmI2 Reagent for Electrosynthetic Application[J]. Chem. Eur. J., 2012, 18(36), 11205 €“ 11209.

[12] Qiu W M and Wang Z Q. Pd-catalysed Reaction of Allylic Acetates with Carbonyl Compounds via Electrochemical Reduction[J]. J. Chem. Soc., Chem. Commun., 1989, 6, 356-357.

[13] Zhang P P, Zhang W C, Zhang T F, et al. The Mechanism of the Palladium-catalysed Reaction of Allylic Acetates with Carbonyl Compounds via Electrochemical Reduction[J]. J. Chem. Soc., Chem. Commun., 1991, 491-492.

[14] Durandetti S, Sibille S, Périchon J. Electrochemical allylation of carbonyl compounds using nickel catalyst and zinc(II) species[J] J. Org. Chem. 1989, 54(9), 2198-2204.

[15] Durandetti S, Meignein C, Périchon J. Iron-Catalyzed Electrochemical Allylation of Carbonyl Compounds by Allylic Acetates[J]. J. Org. Chem., 2003, 68(8), 3121-3124.

[16] (a)Medeiros M J, Pintaric C, Olivero S, et al. Nickel-catalysed electrochemical carboxylation of allylic acetates and carbonates[J]. Electrochimica Acta, 2011, 56(11), 4384€“4389. (b)France D, Olivero S, Duñach E. Intramolecular ally1 transfer reactions catalyzed by electrogenerated nickel-bipyridine complexes: electrosynthesis of homoallylic alcohols[J]. Electrochim. Acta, 1997, 42(13), 2159-2164.

[17] Franco D, Panyella D, Rocamora M, et al. Electrochemical cleavage of allyl aryl ethers and allylation of carbonyl compounds: umpolung of allyl-palladium species[J]. Tetrahedron Letters, 1999, 40(31), 5685-5688.

[18] Olivero S, Franco D, Clinet J C, Duñach E. Electrochemical Reduction of Allyl Ethers in the Presence of Nickel Complexes: a Review of Synthetic Applications[J]. Collect. Czech. Chem. Commun., 2000, 65(6), 844-861.

[19] Franco D, Wenger K, Antonczak S, et al. Intramolecular Allyl Transfer Reaction from Allyl Ether toAldehydeGroups: Experimental and Theoretical Studies[J]. Chem. Eur. J., 2002, 8(3), 664-672.

[20] （a）Li C J, Chan T. Comprehensive Organic Reaction In Aqueous Media[M]. New York, 1997. (b) Li, C J. Aqueous Barbier-Grignard type reaction: Scope, mechanism, and synthetic applications[J]. Tetrahedron, 1996, 52(16), 5643-5668. (c) Li C J. Organtic reactions in aqueous media €“ with a focus on carbon-carbon bond formation[J]. Chem. Rev., 1993, 93(6), 2023-2035. (d) André L, Jacques A, Yves Q. Water-promoted organic reactions[J]. Synthesis, 1994, (8), 741-760. (e) Li C J. Organic reactions in aqueous media with a focus on carbon-carbon bond formations: a decade update[J]. Chem. Rev., 2005, 105(8), 3095-3166.

[21] Zha Z G, Hui A, Zhou Y, et al. A Recyclable Electrochemical Allylation in Water[J]. Org. Lett., 2005, 7(10), 1903-1905.

[22] Huang J M, Dong Y. Zn-mediated electrochemical allylation of aldehydes in aqueous ammonia[J]. Chem. Commun., 2009, (26), 3943-3945.

[23] Huang J M, Ren H R. Electrochemical allylation of carbonyl compounds in aqueous electrolyte catalyzed by zinc[J]. Chem. Commun., 2010, 46(13), 2286-2288.

[24] Zhang L, Zha Z G, Wang Z Y. et al. Aqueous electrosynthesis of carbonyl compounds and the corresponding homoallylic alcohols in a divided cell[J]. Tetrahedron Lett., 2010, 51(10), 1426€“1429.

[25] Zhang L, Zha Z G, Wang Z Y. An efficient electrochemical method for the paired synthesis of carbonyl compounds and homoallylic alcohols in a simple home-made cell[J]. Synlett., 2010, (13), 1915-1918.

[26] Li Z, Zha Z G, Zhang Z L, et al. An electrochemical tandem reaction: one-pot synthesis of homoallylic Alcohols from alcohols in aqueous media[J]. Chem. Commun., 2010, 46(13), 7196-7198.

[27] Sinha A K, Mondal B, Kundu M, et al. Recyclable electrochemical allylation in aqueous ZnCl2medium: synthesis and reactivity of a wire-shaped nano zinc architecture[J]. Org. Chem. Front., 2014, 1(11), 1270€“1275.

[28] Khan F N, Jayakumar R, Pillai C N. Electrochemical reductive allylation of N-benzylideneethanolamine[J]. Tetrahedron Lett., 2002, 43(38), 6807€“6809.

[29] Hilt G, Smoko K I. Indium-catalyzed allylation of imines with electrochemically assisted catalyst regeneration[J]. Tetrahedron Letters. 2002, 43(8), 1437-1439.

[30] Huang J M, Wang X X, Dong Yi. Electrochemical allylation reactions of simple imines in aqueous solution mediated by nanoscale zinc architecture[J]. Angew. Chem. Int. Ed., 2011, 50(4), 924-927.