Synthesis of α,β-alkynyl esters and unsymmetrical maleate esters catalyzed by pd/c; An efficient phosphine-free catalytic system for oxidative alkoxycarbonylation of terminal alkynes

Synlett

Volumn 24, Issue 8, 2013, Pages 981-986

  Gadge, Sandip T ^a   Bhanage, Bhalchandra M ^a  

^a INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

alcohols; alkynes; carbonylation; heterogeneous catalysis; palladium

Indexed keywords

ALCOHOL; ALCOHOL DERIVATIVE; ALKYNE; ALPHA,BETA ALKYNYL ESTER DERIVATIVE; CARBON; CARBON MONOXIDE; ESTER DERIVATIVE; ESTER MALEATE DERIVATIVE; OXYGEN; PALLADIUM; PHENYLACETYLENE; PHOSPHINE; TETRABUTYLAMMONIUM; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL ANALYSIS; CHEMICAL MODIFICATION; CHEMICAL REACTION; CHEMICAL STRUCTURE; OXIDATIVE ALKOXYCARBONYLATION;

EID: 84875289278     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0032-1316896     Document Type: Article

References (44)

1. Lee Y., Kang Y., Chung Y. J. Org. Chem.: 2009; 74 7922
2. Welbes L. L., Lyons T. W., Cychosz K. A., Sanford M. S. J. Am. Chem. Soc.: 2007; 129 5836
3. Pi S.-F, Tang B.-X, Li J.-H, Liu Y.-L, Liang Y. Org. Lett.: 2009; 11 2309
4. Tsujihara T., Takenaka K., Onitsuka K., Hatanaka M., Sasai H. J. Am. Chem. Soc.: 2009; 131 3452
5. Rayabarapu D. K., Tunge J. A. J. Am. Chem. Soc.: 2005; 127 13510
6. Gao H., Zhang J. Chem. Eur. J.: 2012; 18 2777
7. Huang L., Wang Q., Liu X., Jiang H. Angew. Chem. Int. Ed.: 2012; 51 1
8. Yamamoto H., Maruoka K. J. Am. Chem. Soc.: 1981; 103 6133
9. Jana R., Tunge J. A. J. Org. Chem.: 2011; 76 8376
10. Guzikowski A. P., Tamiz A. P., Acosta-Burruel M., Hong-Bae S., Cai S. X., Hawkinson J. E., Keana J. F. W, Kesten S. R., Shipp C. T., Tran M., Whittemore E. R., Woodward R. M., Wright J. L., Zhou Z.-L. J. Med. Chem.: 2000; 43 984
11. Kwong C. K.-W, Fu M. Y., Law H. C.-H, Toy P. H. Synlett: 2010; 2617
12. Zhang W.-Z, Li W.-J, Zhang X., Zhou H., Lu X.-B. Org. Lett.: 2010; 12 4748
13. Inamoto K., Asano N., Kobayashi K., Yonemoto M., Kondo Y. Org. Biomol. Chem.: 2012; 10 1514
14. Fukue Y., Oi S., Inoue Y. J. Chem. Soc., Chem. Commun.: 1994; 2091
15. Gooßen L. J., Rodríguez N., Manjolinho F., Lange P. P. Adv. Synth. Catal.: 2010; 352 2913
16. Tsuji J., Takahashi M., Takahashi T. Tetrahedron Lett.: 1980; 21 849
17. Sakurai Y., Sakaguchi S., Ishii Y. Tetrahedron Lett.: 1999; 40 1701
18. Izawa Y., Shimizu I., Yamamoto A. Bull. Chem. Soc. Jpn.: 2004; 77 2033
19. Heck R. F. J. Am. Chem. Soc.: 1972; 94 2712
20. Alper H., Despeyroux B., Woell J. B. Tetrahedron Lett.: 1983; 24 5691
21. Li J., Jiang H., Jia L. Synth. Commun.: 1999; 29 3733
22. Novakovic K., Mukherjee A., Willis M., Wrighta A., Scottb S. Phys. Chem. Chem. Phys.: 2009; 11 9044
23. Gabriele B., Costa M., Salerno G., Chiusoli G. P. J. Chem. Soc., Perkin Trans. 1: 1994; 83
24. Li J., Jiang H., Chen M. Synth. Commun.: 2001; 31 3131
25. Wu X.-F, Sundararaju B., Neumann H., Dixneuf P. H., Beller M. Chem. Eur. J.: 2011; 17 106
26. Liu Q., Zhang H., Lei A. Angew. Chem. Int. Ed.: 2011; 50 10788
27. Molnar A. Chem. Rev.: 2011; 111 2251
28. Liu J., Chen J., Xia C. J. Catal.: 2008; 253 50
29. Li F., Xia C. J. Catal.: 2004; 227 542
30. Mori S., Yanase T., Aoyagi S., Monguchi Y., Maegawa T., Sajiki H. Chem. Eur. J.: 2008; 14 6994
31. Mori S., Takubo M., Yanase T., Maegawa T., Monguchi Y., Sajiki H. Adv. Synth. Catal.: 2010; 352 1630
32. Gupte S. P., Chaudhari R. V. J. Catal.: 1988; 114 246
33. Khedkar M. V., Khan S. R., Sawant D. N., Bagal D. B., Bhanage B. M. Adv. Synth. Catal.: 2011; 353 3415
34. Sawant D. N., Wagh Y. S., Bhatte K. D., Bhanage B. M. J. Org. Chem.: 2011; 76 5489
35. Tambade P. J., Patil Y. P., Bhanushali M. J., Bhanage B. M. Synthesis: 2008; 2347
36. Khedkar M. V., Tambade P. J., Qureshi Z. S., Bhanage B. M. Eur. J. Org. Chem.: 2010; 6981
37. Qureshi Z. S., Deshmukh K. M., Tambade P. J., Bhanage B. M. Synthesis: 2011; 243
38. Khedkar M. V., Khan S. R., Dhake K. P., Bhanage B. M. Synthesis: 2012; 44 2623
39. Gupte S. P., Chaudhari R. V. Ind. Eng. Chem. Res.: 1992; 31 2069
40. Gabriele B., Salerno G., Costa M. Top. Organomet. Chem.: 2006; 18 239
41. Maitlis P. M., Haynes A., James B. R., Catellanic M., Chiusoli G. P. Dalton Trans.: 2004; 3904
42. Vaughan W. R., Andersen K. S. J. Org. Chem.: 1956; 21 673
43. Ji J., Lu X. Tetrahedron: 1994; 50 9067
44. Butt, G.; Topsom, R. D. Spectrochim. Acta, Part A 1982, 38,649.