Synthesis of α-Hydroxycarboxylic Acid Anilides via Copper-Catalyzed C–N Coupling of α-Hydroxyamides with Aryl Halides

Abstract

The synthesis of highly important α-hydroxycarboxylic acid anilides via copper-catalyzed chemoselective C–N coupling reactions of α-hydroxyamides and aryl halides is described. This highly selective N-arylation process demonstrates wide substrate scope, cost savings and easy operation. In addition, the chirality of l-3-phenyllactamide is preserved during the reaction.

Key words

α-hydroxycarboxylic acid anilides - copper - cross-coupling - α-hydroxyamides - catalysis - chemoselectivity

• References

• 1 Wang Y.-S, Hwang K.-L, Chen Y.-L. Pestic. Sci. 1994; 42: 53
• 2 Sugaya K, Ikeda Y, Goh A, Konno K, Tanaka M. Weed Res., Jpn. 1986; 31: 149
• 3 Gertz EW, Wisneski JA, Chiu D, Akin JR, Hu C. J. Am. Coll. Cardiol. 1985; 5: 250
• 4 Hopkins RM, Adams MD, Lau DH. M, Creighton JM, Hoey GB. Radiology 1981; 140: 713
• 5 Shapiro SL, Rose IM, Freedman L. J. Am. Chem. Soc. 1959; 81: 6322
• 6a Schellhammer PF. Expert Opin. Pharmacother. 2002; 3: 1313
• 6b Kunkler I, James N, Maher J. Expert Rev. Anticancer Ther. 2004; 4: 37
• 7 Müderris II, Bayram F, Ozçelik B, Güven M. Gynecol. Endocrinol. 2002; 16: 63
• 8 Serra C, Sandor NL, Jang H, Lee D, Toraldo G, Guarneri T, Wong S, Zhang A, Guo W, Jasuja R, Bhasin S. Endocrinology 2013; 154: 4594
• 9 Schwartz A, Madan PB, Mohacsi E, O’Brien JP, Todaro LJ, Coffen DL. J. Org. Chem. 1992; 57: 851
• 10 Awasthi A, Singh MK, Singh AT, Jaggi M, Lohani M. J. Enzyme Inhib. Med. Chem. 2014; 29: 710
• 11 Henning S, Markus F, Jochen G, Herman S. WO2008/31509 A1, 2008
• 12a Su T, Zhu B.-Y. US6638980 B1, 2003
• 12b Delaney NG. US4963539 A1, 1990
• 13 Klaholz BP, Mitschler A, Belema M, Zusi C, Moras D. PNAS 2000; 97: 6322
• 14 Ylijoki KE. O, Kündig EP. Chem. Commun. 2011; 47: 10608
• 15 Katritzky AR, He H.-Y, Suzuki K. J. Org. Chem. 2000; 65: 8210
• 16a Seebach D, Adam G, Gees T, Schiess M, Weigand W. Chem. Ber. 1988; 121: 507
• 16b Denmark SE, Fan Y. J. Am. Chem. Soc. 2003; 125: 7825
• 17 Shin JM, Kim YH. Tetrahedron Lett. 1986; 27: 1921
• 18 Zhang M, Imm S, Bähn S, Neubert L, Neumann H, Beller M. Angew. Chem. Int. Ed. 2012; 51: 3905
• 19 Mamillapalli NC, Sekar G. Chem. Commun. 2014; 50: 7881
• 20 Klapars A, Huang X, Buchwald SL. J. Am. Chem. Soc. 2002; 124: 7421
• 21 Wolter M, Klapars A, Buchwald SL. Org. Lett. 2001; 3: 3803
• 22 Job GE, Buchwald SL. Org. Lett. 2002; 4: 3703
• 23 Huang X, Anderson KW, Zim D, Jiang L, Klapars A, Buchwald SL. J. Am. Chem. Soc. 2003; 125: 6653
• 24 Maiti D, Buchwald SL. J. Am. Chem. Soc. 2009; 131: 17423
• 25 Maiti D. Chem. Commun. 2011; 47: 8340
• 26 Ueda S, Buchwald SL. Angew. Chem. Int. Ed. 2012; 51: 10364
• 27a Dong J, Wang Y, Xiang Q, Lv X, Weng W, Zeng Q. Adv. Synth. Catal. 2013; 355: 692
• 27b Wang Y, Tu X, Lv X, Zhou L, Zeng Q. Tetrahedron Lett. 2013; 54: 6045
• 28a Dai C, Sun X, Tu X, Wu L, Zhan D, Zeng Q. Chem. Commun. 2012; 48: 5367
• 28b Sun X, Tu X, Dai C, Zhang X, Zhang B, Zeng Q. J. Org. Chem. 2012; 77: 4454
• 29 Monnier F, Taillefer F. Angew. Chem. Int. Ed. 2009; 48: 6954
• 30 Ballinger P, Long FA. J. Am. Chem. Soc. 1960; 82: 795
• 31 Branch GE. K, Clayton JO. J. Am. Chem. Soc. 1928; 50: 1680
• 32 Chiang Y, Guo H.-X, Kresge AJ, Richard JP, Toth K. J. Am. Chem. Soc. 2003; 125: 187
• 33 Mamillapalli NC, Sekar G. RSC Adv. 2014; 4: 61077
• 34 Kambe N, Inoue T, Takeda T, Fujiwara SI, Sonoda N. J. Am. Chem. Soc. 2006; 128: 12650
• 35 Brooks RE, Edwards JO, Levey G, Smyth F. Tetrahedron 1966; 22: 1279
• 36 Kostikov RR, Khlebnikov AF, Ogloblin KA. Zh. Org. Khim. 1973; 9: 2346
• 37 Haddadin MJ, Tannus HT. Heterocycles 1984; 22: 773
• 38 Girreser N. Synthesis 1995; 1223
• 39 Banik BK, Barakat KJ, Wagle DR, Manhas MS, Bose AK. J. Org. Chem. 1999; 64: 5746
• 40 Brand K, Priesner R. Arch. Pharm. 1952; 285: 26