Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Synthesis 2014; 46(03): 320-330
DOI: 10.1055/s-0033-1340317
DOI: 10.1055/s-0033-1340317
paper
One-Pot Transition-Metal-Free Synthesis of Weinreb Amides Directly from Carboxylic Acids
Further Information
Publication History
Received: 16 September 2013
Accepted after revision: 08 November 2013
Publication Date:
12 December 2013 (online)
Abstract
Weinreb amides were prepared directly from carboxylic acids, N,O-dimethylhydroxylamine, and phosphorus trichloride in one pot at 60 °C in toluene in high yields, thus avoiding the separation of the moisture and air sensitive intermediate P[NMe(OMe)]3 in advance. Sterically hindered carboxylic acids also give the corresponding Weinreb amides in excellent yields. Various functional groups are tolerated on the carboxylic acid. The method, which is a simple process and gives high yields, is suitable for large-scale production.
Supporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis.
- Supporting Information
-
References
- 1 Nahm S, Weinreb SM. Tetrahedron Lett. 1981; 22: 3815
- 2 Khlestkin VK, Mazhukin DG. Curr. Org. Chem. 2003; 7: 967
- 3 Singh J, Satyamurthi N, Aidhen IS. J. Prakt. Chem. 2000; 342: 340
- 4 Parhi AK, Franck RW. Org. Lett. 2004; 6: 3063
- 5 Ruiz J, Sotomayor N, Lete E. Org. Lett. 2003; 5: 1115
- 6 Taillier C, Bellosta V, Meyer C, Cossy J. Org. Lett. 2004; 6: 2145
-
7 Yang F, Ackermann L. Org. Lett. 2013; 15: 718
- 8 Spletstoser JT, White JM, Tunoori AR, Georg GI. J. Am. Chem. Soc. 2007; 129: 3408
- 9 Murphy JA, Commeureuc AG. J, Snaddon TN, McGuire TM, Khan TA, Hisler K, Dewis ML, Carling R. Org. Lett. 2005; 7: 1427
- 10 Hisler K, Tripoli R, Murphy JA. Tetrahedron Lett. 2006; 47: 6293
- 11 He W, Huang J, Sun X, Frontier AJ. J. Am. Chem. Soc. 2008; 130: 300
- 12 Custar DW, Zabawa TP, Scheidt KA. J. Am. Chem. Soc. 2008; 130: 804
- 13 Gibson CL, Handa S. Tetrahedron: Asymmetry 1996; 7: 1281
- 14 Goel OP, Krolls U, Stier M, Kesten S. Org. Synth. 1989; 67: 69
- 15 Nitz TJ, Volkots DL, Aldous DJ, Oglesby RC. J. Org. Chem. 1994; 59: 5828
- 16 Goel OP, Krolls U. Org. Prep. Proced. Int. 1987; 19: 75
- 17 Sha CK, Huang SJ, Zhan ZP. J. Org. Chem. 2002; 67: 831
- 18 Jaipuri FA, Jofre MF, Schwarz KA, Pohl NL. Tetrahedron Lett. 2004; 45: 4149
- 19 Shimizu T, Osako K, Nakata T. Tetrahedron Lett. 1997; 38: 2685
- 20 Dineen TA, Zajac MA, Myers AG. J. Am. Chem. Soc. 2006; 128: 16406
- 21 Jacobi PA, Kaczmarek CS. R, Udodong UE. Tetrahedron Lett. 1984; 25: 4859
- 22 Shreder K, Zhang L, Goodman M. Tetrahedron Lett. 1998; 39: 221
- 23 Braun M, Waldmuller D. Synthesis 1989; 856
- 24 Falorni M, Giacomelli G, Spanedda AM. Tetrahedron: Asymmetry 1998; 9: 3039
- 25 Dechantsreiter MA, Burkhart F, Kessler H. Tetrahedron Lett. 1998; 39: 253
- 26 Sibi MP, Stessman CC, Schultz JA, Christensen JW, Lu J, Marvin M. Synth. Commun. 1995; 25: 1255
- 27 Tunoori AR, White JM, Georg GI. Org. Lett. 2000; 2: 4091
- 28 DeLuca L, Giacomelli G, Taddei M. J. Org. Chem. 2001; 66: 2534
- 29 Nemoto H, Ma R, Moriguchi H, Kawamura T, Kamiya M, Shibuya M. J. Org. Chem. 2007; 72: 9850
- 30 Krishnamoorthy R, Lam SQ, Manley CM, Herr RJ. J. Org. Chem. 2010; 75: 1251
- 31 Murakami M, Hoshino Y, Ito H, Ito Y. Chem. Lett. 1998; 163
- 32 Martinelli JR, Watson DA, Freckmann DM. M, Barder TE, Buchwald SL. J. Org. Chem. 2008; 73: 7102
- 33 Martinelli JR, Freckmann DM. M, Buchwald SL. Org. Lett. 2006; 8: 4843
- 34 Deagostino A, Larini P, Occhiato EG, Pizzuto L, Prandi C, Venturello P. J. Org. Chem. 2008; 73: 1941
- 35 Woo JC. S, Fenster E, Dake GR. J. Org. Chem. 2004; 69: 8984
- 36 Aungst RA. Jr, Funk RL. J. Am. Chem. Soc. 2001; 123: 9455
- 37 Wieckowska A, Fransson R, Odell LR, Larhed M. J. Org. Chem. 2011; 76: 978
- 38 Niu T, Zhang W, Huang D, Xu C, Wang H, Hu Y. Org. Lett. 2009; 11: 4474
- 39 Brunette SR, Lipton MA. J. Org. Chem. 2000; 65: 5114
- 40 Rudzinski DM, Kelly CB, Leadbeater NE. Chem. Commun. 2012; 48: 9610
- 41 Jithunsa M, Ueda M, Miyata O. Org. Lett. 2011; 13: 518
- 42 Ende CW, Zhou Z, Parker KA. J. Am. Chem. Soc. 2013; 135: 582
- 43 Kerr WJ, Morrison AJ, Pazicky M, Weber T. Org. Lett. 2012; 14: 2250
- 44 Baettig U, D’Souza A.-M, Hunt P, Press NJ, Watson SJ. US 2010029670, 2010
- 45 Yun JI, Kim HR, Kim SK, Kim D, Lee J. Tetrahedron 2012; 68: 1177
- 46 García-Domínguez P, Lepore I, Erb C, Gronemeyer H, Altucci L, Álvarez R, de Lera AR. Org. Biomol. Chem. 2011; 9: 6979
- 47 Shen Z, Dornan P, Khan HA, Woo TK, Dong VM. J. Am. Chem. Soc. 2009; 131: 1077
- 48 Marsilje TH, Hedrick MP, Desharnais J, Tavassoli A, Zhang Y, Wilson IA, Benkovic SJ, Boger DL. Bioorg. Med. Chem. 2003; 11: 4487
- 49 Rusch M, Zahov S, Vetter IR, Lehr M, Hedberg C. Bioorg. Med. Chem. 2012; 20: 1100
- 50 García-Domínguez P, Alvarez R, de Lera ÁR. Eur. J. Org. Chem. 2012; 4762
- 51 Lescop C, Herzner H, Siendt H, Bolliger R, Henneböhle M, Weyermann P, Briguet A, Courdier-Fruh I, Erb M, Foster M, Meier T, Magyar JP, Sprecher AV. Bioorg. Med. Chem. Lett. 2005; 15: 5176
- 52 Unthank M, Tavassoli B, Aggarwal VK. Org. Lett. 2008; 10: 1501
- 53 Capela R, Oliveira R, Gonçalves LM, Domingos A, Gut J, Rosenthal PJ, Lopes F, Moreira R. Bioorg. Med. Chem. Lett. 2009; 19: 3229
- 54 Whipple WL, Reich HJ. J. Org. Chem. 1991; 56: 2912
- 55 Harding M, Hodgson R, Nelson A. J. Chem. Soc., Perkin Trans. 1 2002; 2403
- 56 Patel BH, Heath SF. A, Mason AM, Barrett AG. M. Tetrahedron Lett. 2011; 52: 2258