Copper-Catalyzed O-Methylation of Carboxylic Acids Using DMSO as a Methyl Source

Abstract

A copper-catalyzed O-methylation of carboxylic acids using dimethyl sulfoxide (DMSO) as the methyl source is disclosed. This transformation exhibits a broad substrate scope and excellent functional group tolerance. Mechanistic studies indicate that a methyl radical is generated from dimethyl sulfoxide in the reaction process.

Key words

carboxylic acids - O-methylation - dimethyl sulfoxide - hydrogen peroxide - methyl radical - esterification - esters

• References

• 1a Kelly TR, Lang F. J. Org. Chem. 1996; 61: 4623
• 1b Crimmins MT, Pace JM, Nantermet PG, Kim-Meade AS, Thomas JB, Watterson SH, Wagman AS. J. Am. Chem. Soc. 2000; 122: 8453
• 1c Allen JG, Danishefsky SJ. J. Am. Chem. Soc. 2001; 123: 351
• 1d Garg NK, Sarpong R, Stoltz BM. J. Am. Chem. Soc. 2002; 124: 13179
• 1e Mascitti V, Corey EJ. J. Am. Chem. Soc. 2004; 126: 15664
• 1f Stivala CE, Zakarian A. J. Am. Chem. Soc. 2008; 130: 3774
• 1g Movassaghi M, Tjandra M, Qi J. J. Am. Chem. Soc. 2009; 131: 9648
• 1h Chang J.-S, Lee Y.-D, Chou LC.-S, Ling T.-R, Chou T.-C. Ind. Eng. Chem. Res. 2012; 51: 655
• 1i Zheng P, Somersan-Karakaya S, Lu S, Roberts J, Pingle M, Warrier T, Little D, Guo X, Brickner SJ, Nathan CF, Gold B, Liu G. J. Med. Chem. 2014; 57: 3755
• 1j Deng Y, Shipps GW. Jr, Cooper A, English JM, Annis DA, Carr D, Nan Y, Wang T, Zhu HY, Chuang CC, Dayananth P, Hruza AW, Xiao L, Jin W, Kirschmeier P, Windsor WT, Samatar AA. J. Med. Chem. 2014; 57: 8817
• 1k Deng J, Zhou S, Zhang W, Li J, Li R, Li A. J. Am. Chem. Soc. 2014; 136: 8185
• 1l Qin T, Porco JA. Jr. Angew. Chem. Int. Ed. 2014; 53: 3107
• 1m Neufeld K, Henssen B, Pietruszka J. Angew. Chem. Int. Ed. 2014; 53: 13253
• 1n Mita T, Higuchi Y, Sato Y. Org. Lett. 2014; 16: 14
• 1o Smith JM, Moreno J, Boal BW, Garg NK. J. Org. Chem. 2015; 80: 8954
• 2 Lamoureux G, Aguero C. ARKIVOC 2009; (i): 251 ; http://www.arkat-usa.org/home
• 3 Zhu Y, Yan H, Lu L, Liu D, Rong G, Mao J. J. Org. Chem. 2013; 78: 9898
• 4 Xia Q, Liu X, Zhang Y, Chen C, Chen W. Org. Lett. 2013; 15: 3326
• 5a Selva M, Tundo P. J. Org. Chem. 2006; 71: 1464
• 5b Aricò F, Tundo P. Russ. Chem. Rev. 2010; 79: 479
• 5c Ji Y, Sweeney J, Zoglio J, Gorin DJ. J. Org. Chem. 2013; 78: 11606
• 6a Jiang Y, Pan S, Zhang Y, Yu J, Liu H. Eur. J. Org. Chem. 2014; 2027
• 6b Jacobson CE, Martinez-Munoz N, Gorin DJ. J. Org. Chem. 2015; 80: 7305
• 7a Liang Y.-F, Wu K, Song S, Li X, Huang X, Jiao N. Org. Lett. 2015; 17: 876
• 7b Song S, Huang X, Liang Y.-F, Tang C, Li X, Jiao N. Green Chem. 2015; 17: 2727
• 8 Ren X, Chen J, Chen F, Cheng J. Chem. Commun. 2011; 47: 6725
• 9 Kawakami T, Suzuki H. Tetrahedron Lett. 2000; 41: 7093
• 10 Fei H, Yu J, Jiang Y, Guo H, Cheng J. Org. Biomol. Chem. 2013; 11: 7092
• 11 Cao H, Lei S, Li N, Chen L, Liu J, Cai H, Qiu S, Tan J. Chem. Commun. 2015; 51: 1823
• 12a Qian J, Zhang Z, Liu Q, Liu T, Zhang G. Adv. Synth. Catal. 2014; 356: 3119
• 12b Zhang Z, Tian Q, Qian J, Liu Q, Liu T, Shi L, Zhang G. J. Org. Chem. 2014; 79: 8182
• 13a Yin G, Zhou B, Meng X, Wu A, Pan Y. Org. Lett. 2006; 8: 2245
• 13b Chu L, Yue X, Qing F.-L. Org. Lett. 2010; 12: 1644
• 13c Luo F, Pan C, Li L, Chen F, Cheng J. Chem. Commun. 2011; 47: 5304
• 13d Dai C, Xu Z, Huang F, Yu Z, Gao YF. J. Org. Chem. 2012; 77: 4414
• 13e Liu F.-L, Chen J.-R, Zou Y.-Q, Wei Q, Xiao W.-J. Org. Lett. 2014; 16: 3768
• 13f Hu G, Xu J, Li P. Org. Lett. 2014; 16: 6036
• 13g Gao Q, Liu S, Wu X, Wu A. Tetrahedron Lett. 2014; 55: 6403
• 13h Gao Q, Wu X, Li Y, Liu S, Meng X, Wu A. Adv. Synth. Catal. 2014; 356: 2924
• 13i Mal K, Sharma A, Maulik PR, Das I. Chem. Eur. J. 2014; 20: 662
• 14a Yuan G, Zheng J, Gao X, Li X, Huang L, Chen H, Jiang H. Chem. Commun. 2012; 48: 7513
• 14b Jiang Y, Loh T.-P. Chem. Sci. 2014; 5: 4939
• 14c Gao X, Pan X, Gao J, Huang H, Yuan G, Li Y. Chem. Commun. 2015; 51: 210
• 15 Bansal V, Thapliyal PC, Khanna RN. Synth. Commun. 1995; 25: 1669
• 16 Yao B, Song R.-J, Liu Y, Xie Y.-X, Li J.-H, Wang M.-K, Tang R.-Y, Zhang X.-G, Deng C.-L. Adv. Synth. Catal. 2012; 354: 1890
• 17 Jiang X, Wang C, Wei Y, Xue D, Liu Z, Xiao J. Chem. Eur. J. 2014; 20: 58
• 18a Kondo T, Kirschenbaum LJ, Kim H, Riesz P. J. Phys. Chem. 1993; 97: 522
• 18b Keddie DJ, Johnson TE, Arnold DP, Bottle SE. Org. Biomol. Chem. 2005; 3: 2593
• 18c Baptista L, Clemente da Silva E, Arbilla G. Phys. Chem. Chem. Phys. 2008; 10: 6867
• 19a Guimaraes IR, Giroto A, Oliveira LC. A, Guerreiro MC, Lima DQ, Fabris JD. Appl. Catal., B 2009; 91: 581
• 19b Xia M, Long M, Yang Y, Chen C, Cai W, Zhou B. Appl. Catal., B 2011; 110: 118
• 19c Zhang L, Nie Y, Hu C, Qu J. Appl. Catal., B 2012; 125: 418
• 19d La Penna G, Hureau C, Andreussi O, Faller P. J. Phys. Chem. B 2013; 117: 16455
• 19e Ling Y, Long M, Hu P, Chen Y, Huang J. J. Hazard. Mater. 2014; 264: 195
• 19f Kim S, Ginsbach JW, Lee JY, Peterson RL, Liu JJ, Siegler MA, Sarjeant AA, Solomon EI, Karlin KD. J. Am. Chem. Soc. 2015; 137: 2867
• 19g Wang Y, Zhao H, Zhao G. Appl. Catal., B 2015; 164: 396
• 19h Lyu L, Zhang L, Wang Q, Nie Y, Hu C. Environ. Sci. Technol. 2015; 49: 8639
• 20a Huang F, Quach TD, Batey RA. Org. Lett. 2013; 15: 3150
• 20b Tran BL, Driess M, Hartwig JF. J. Am. Chem. Soc. 2014; 136: 17292
• 21 Jiang Q, Zhao A, Xu B, Jia J, Liu X, Guo C. J. Org. Chem. 2014; 79: 2709
• 22 Natte K, Dumrath A, Neumann H, Beller M. Angew. Chem. Int. Ed. 2014; 53: 10090
• 23 Zhang N, Yang R, Zhang-Negrerie D, Du Y, Zhao K. J. Org. Chem. 2013; 78: 8705
• 24 Li P, Zhao J, Lang R, Xia C, Li F. Tetrahedron Lett. 2014; 55: 390
• 25 Lu W, Chen J, Liu M, Ding J, Gao W, Wu H. Org. Lett. 2011; 13: 6114
• 26 González I, Mosquera J, Guerrero C, Rodríguez R, Cruces J. Org. Lett. 2009; 11: 1677
• 27 Kantam ML, Yadav J, Laha S, Srinivas P, Sreedhar B, Figueras F. J. Org. Chem. 2009; 74: 4608
• 28 Davies SG, Fletcher AM, Roberts PM, Smith AD. Tetrahedron 2009; 65: 10192
• 29 Heller ST, Sarpong R. Org. Lett. 2010; 12: 4572
• 30 Yamamoto N, Obora Y, Ishii Y. J. Org. Chem. 2011; 76: 2937
• 31 Baquey G, Moine L, Babot O, Degueil M, Maillard B. Polymer 2005; 46: 6283