Citation:
Lin He, Hao Guo, Xiao-Wei Ma, Jie Zhang, Cheng-Zhi Gu, Wei Wang, Bin Dai. N-Heterocyclic carbene-catalyzed synthesis of acetyltributylcitrate via a transesterification reaction[J]. Chinese Chemical Letters,
;2014, 25(2): 215-217.
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A new methodology for the synthesis of a green plasticizer acetyltributylcitrate through a transesterification reaction was developed. Under the catalysis of alkyl-substituted imidazol-type N-heterocyclic carbenes, tributyl citrate can react with vinyl acetate smoothly to give ATBC in high yield.
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[1]
[1] S. Díez-González, N. Marion, S.P. Nolan, N-heterocyclic carbenes in late transition metal catalysis, Chem. Rev. 109 (2009) 3612-3676.
-
[2]
[2] (a) D. Enders, O. Niemeier, A. Henseler, Organocatalysis by N-heterocyclic carbenes, Chem. Rev. 107 (2007) 5606-5655; (b) N. Marion, S. Díez-González, S.P. Nolan, N-heterocyclic carbenes as organocatalysts, Angew. Chem. Int. Ed. 46 (2007) 2988-3000; (c) V. Nair, S. Vellalath, B.P. Babu, Recent advances in carbon-carbon bondforming reactions involving homoenolates generated by NHC catalysis, Chem. Soc. Rev. 37 (2008) 2691-2698; (d) D. Enders, A. Grossmann, N-heterocyclic carbene catalyzed domino reactions, Angew. Chem. Int. Ed. 51 (2012) 314-325.
-
[3]
[3] (a) D. Enders, A. Grossmann, J. Fronert, G. Raabe, N-heterocyclic carbene catalysed asymmetric cross-benzoin reactions of heteroaromatic aldehydes with trifluoromethyl ketones, Chem. Commun. 46 (2010) 6282-6284; (b) D. Enders, A. Henseler, A direct intermolecular cross-benzoin type reaction: N-heterocyclic carbene-catalyzed coupling of aromatic aldehydes with trifluoromethyl ketones, Adv. Synth. Catal. 351 (2009) 1749-1752.
-
[4]
[4] (a) T. Jousseaume, N.E. Wurz, F. Glorius, Highly enantioselective synthesis of aamino acid derivatives by an NHC-catalyzed intermolecular Stetter reaction, Angew. Chem. Int. Ed. 50 (2011) 1410-1414; (b) X.Q. Fang, X.K. Chen, H. Lv, Y.R. Chi, Enantioselective Stetter reactions of enals and modified chalcones catalyzed by N-heterocyclic carbenes, Angew. Chem. Int. Ed. 50 (2011) 11782-11785; (c) D.A. DiRocco, T. Rovis, Catalytic asymmetric intermolecular Stetter reaction of enals with nitroalkenes: enhancement of catalytic efficiency through bifunctional additives, J. Am. Chem. Soc. 133 (2011) 10402-10405.
-
[5]
[5] (a) X.K. Chen, X.Q. Fang, Y.R. Chi, cis-Enals in N-heterocyclic carbene-catalyzed reactions: distinct stereoselectivity and reactivity, Chem. Sci. 4 (2013) 2613- 2618; (b) D.T. Cohen, K.A. Scheidt, Cooperative Lewis acid/N-heterocyclic carbene catalysis, Chem. Sci. 3 (2012) 53-57; (c) J.M. Mo, X.K. Chen, Y.R. Chi, Oxidative, g-Addition of enals to trifluoromethyl ketones: enantioselectivity control via Lewis acid/N-heterocyclic carbene cooperative catalysis, J. Am. Chem. Soc. 134 (2012) 8810-8813.
-
[6]
[6] (a) D.A. DiRocco, T. Rovis, Catalytic asymmetric α-acylation of tertiary amines mediated by a dual catalysis mode: N-heterocyclic carbene and photoredox catalysis, J. Am. Chem. Soc. 134 (2012) 8094-8097; (b) Y.M. Zhao, Y. Tam, Y.J. Wang, Z. Li, J. Sun, N-heterocyclic carbene-catalyzed internal redox reaction of alkynals: an efficient synthesis of allenoates, Org. Lett. 14 (2012) 1398-1401; (c) F.G. Sun, L.H. Sun, S. Ye, N-heterocyclic carbene-catalyzed enantioselective annulation of bromoenal and 1,3-dicarbonyl compounds, Adv. Synth. Catal. 353 (2011) 3134-3138; (d) X.B. Wang, X.L. Zou, G.F. Du, Z.Y. Liu, B. Dai, Nucleophilic carbene-catalyzed redox-esterification reaction of a-halo-a,b-unsaturated aldehyde, Tetrahedron 68 (2012) 6498-6503.
-
[7]
[7] (a) J.J. Song, F. Gallou, J.T. Reeves, et al., Activation of TMSCN by N-heterocyclic carbenes for facile cyanosilylation of carbonyl compounds, J. Org. Chem. 71 (2006) 1273-1276; (b) Y. Suzuki, A. Bakar, K. Muramatsu, M. Sato, Cyanosilylation of aldehydes catalyzed by N-heterocyclic carbenes, Tetrahedron 62 (2006) 4227-4231; (c) J. Zhang, G.F. Du, Y.K. Xu, L. He, B. Dai, N-heterocyclic carbene catalyzed cyanation reaction of carbonyl compounds with ethyl cyanoformate and acetyl cyanide, Tetrahedron Lett. 52 (2011) 7153-7156.
-
[8]
[8] (a) J.J. Song, Z.L. Tan, J.T. Reeves, N.K. Yee, C.H. Senanayake, N-heterocyclic carbene-catalyzed Mukaiyama aldol reactions, Org. Lett. 9 (2007) 1013-1016; (b) G.F. Du, L. He, C.Z. Gu, B. Dai, N-heterocyclic carbene catalyzed vinylogous aldol reaction of 2-(trimethylsilyloxy) furan and aldehydes, Synlett (2010) 2513- 2517.
-
[9]
[9] (a) T.Y. Jian, L. He, C. Tang, S. Ye, N-heterocyclic carbene catalysis: enantioselective formal [2+2] cycloaddition of ketenes and N-sulfinylanilines, Angew. Chem. Int. Ed. 50 (2011) 9104-9107; (b) X.D. Zhao, K.E. Ruhl, T. Rovis, N-heterocyclic-carbene-catalyzed asymmetric oxidative hetero-Diels-Alder reactions with simple aliphatic aldehydes, Angew. Chem. Int. Ed. 51 (2012) 12330-12333; (c) J. Dugal-Tessier, E.A. O'Bryan, T.B.H. Schroeder, D.T. Cohen, K.A. Scheidt, An Nheterocyclic carbene/Lewis acid strategy for the stereoselective synthesis of spirooxindole lactones, Angew. Chem. Int. Ed. 51 (2012) 4963-4967; (d) L. Candish, D.W. Lupton, N-heterocyclic carbene-catalyzed Ireland-coates Claisen rearrangement: synthesis of functionalized b-lactones, J. Am. Chem. Soc. 135 (2013) 58-61.
-
[10]
[10] G.A. Grasa, R.M. Kissling, S.P. Nolan, N-heterocyclic carbenes as versatile nucleophilic catalysts for transesterification/acylation reactions, Org. Lett. 4 (2002) 3583-3586.
-
[11]
[11] G.W. Nyce, J.A. Lamboy, E.F. Connor, R.M. Waymouth, J.L. Hedrick, Expanding the catalytic activity of nucleophilic N-heterocyclic carbenes for transesterification reactions, Org. Lett. 4 (2002) 3587-3590.
-
[12]
[12] (a) G.A. Grasa, R. Singh, S.P. Nolan, Transesterification/acylation reactions catalyzed by molecular catalysts, Synthesis (2004) 971-985; (b) M. Fèvre, J. Pinaud, Y. Gnanou, J. Vignolle, D. Taton, N-heterocyclic carbenes (NHCs) as organocatalysts and structural components in metal-free polymer synthesis, Chem. Soc. Rev. 42 (2013) 2142-2172.
-
[13]
[13] A. Sakakura, S. Nakagawa, K. Ishihara, Bulky diarylammonium arenesulfonates as mild and extremely active dehydrative ester condensation catalysts, Tetrahedron 62 (2006) 422-433.
-
[14]
[14] A. Sakakura, K. Kawajiri, T. Ohkubo, Y. Kosugi, K. Ishihara, Widely useful DMAPcatalyzed esterification under auxiliary base- and solvent-free conditions, J. Am. Chem. Soc. 129 (2007) 14775-14779.
-
[15]
[15] (a) Z.H. Cai, G.F. Du, L. He, C.Z. Gu, B. Dai, N-heterocyclic carbene catalyzed hydrophosphonylation of aldehydes, Synthesis (2011) 2073-2078; (b) Y.C. Fan, G.F. Du, W.F. Sun, W. Kang, L. He, N-heterocyclic carbene-catalyzed cyanomethylation of aldehydes with TMSAN, Tetrahedron Lett. 53 (2012) 2231- 2233; (c) X.L. Zou, G.F. Du, W.F. Sun, et al., N-heterocyclic carbene mediated Reformatsky reaction of aldehydes with a-trimethylsilylcarbonyl compounds, Tetrahedron 69 (2013) 607-612.
-
[16]
[16] A.J. Arduengo Ⅲ, R. Krafczyk, R. Schmutzler, Imidazolylidenes, imidazolinylidenes and imidazolidines, Tetrahedron 55 (1999) 14523-14534.
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