Iodide-catalyzed reductions: Development of a synthesis of phenylacetic acids

Journal of Organic Chemistry

Volumn 76, Issue 22, 2011, Pages 9519-9524

  Milne, Jacqueline E ^a   Storz, Thomas ^a   Colyer, John T ^a   Thiel, Oliver R ^a   Dilmeghani Seran, Mina ^a   Larsen, Robert D ^a   Murry, Jerry A ^a  

^a AMGEN INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

HYDROIODIC ACID; IN-SITU; MANDELIC ACID; PHENYLACETIC ACID; PHOSPHORUS ACID; REDUCTANTS; SCALABLE SYNTHESIS; SODIUM IODIDES;

PHOSPHORUS; SODIUM;

CATALYSIS;

2 (5 CHLORO 2 FLUORO 4 METHOXYPHENYL) 2 HYDROXYACETONITRILE; 3,4 METHYLENEDIOXYPHENYLACETIC ACID; 4 BROMOPHENYLACETIC ACID; 4 HYDROXYPHENYLACETIC ACID; CYCLOHEXYLPHENYLACETIC ACID; DIPHENYLACETIC ACID; FUNCTIONAL GROUP; HYDRATROPIC ACID; MANDELIC ACID; PHENYLACETIC ACID; PHOSPHORUS ACID DERIVATIVE; SODIUM IODIDE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; REDUCTION; STOICHIOMETRY; SYNTHESIS;

ACIDS; CATALYSIS; IODIDES; IODINE COMPOUNDS; MANDELIC ACIDS; MOLECULAR STRUCTURE; OXIDATION-REDUCTION; PHENYLACETATES; STEREOISOMERISM;

EID: 81055147731     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo2018087     Document Type: Article

References (44)

1. Antityrosinase and antimicrobial: Yu-Jing Zhu, H.-T.; Zhou, Y.-H.; Hu, J.-Y.; Tang, M.-X.; Su, Y.-J.; Guo, Q.-X.; Chen, B. L. Food Chem. 2011, 298
2. Antifungal: Xu, L.; Feng, N.; Xue, J.; Wu, P.; Wei, X. Redai Yaredai Zhiwu Xuebao 2008, 16, 140
3. Pd-catalyzed α-arylation: Moradi, W. A.; Buchwald, S. L. J. Am. Chem. Soc. 2001, 123, 7996
4. Hama, T.; Hartwig, J. F. Org. Lett. 2008, 10, 1549
5. Rh-catalyzed carbonylation: Giroux, A.; Nadeau, C.; Han, Y. Tetrahedron Lett. 2000, 41, 7601
6. One carbon elongation of aldehydes: Huh, D. H.; Jeong, J. S.; Lee, H. B.; Ryu, H.; Kim, Y. G. Tetrahedron 2002, 58, 9925
7. Zhou, G.-B.; Zhang, P.-F.; Pan, Y.-J. Tetrahedron 2005, 61, 5671
8. Pd-catalyzed carbonylation: Kohlpaintner, C. W.; Beller, M. J. Mol. Catal. A: Chem. 1997, 116, 259
9. Willerodt-Kindler: Alam, M. M.; Adapa, S. R. Synth. Commun. 2003, 33, 59
10. Reduction of mesylates: Inokuchi, T.; Sugimoto, T.; Kusumoto, M.; Torii, S. Bull. Chem. Soc. Jpn. 1992, 65, 3200
11. Nakamura, K.; Yasui, S.; Ohno, A.; Oka, S. Tetrahedron Lett. 1983, 24, 2001
12. Green chemistry review: Tucker, J. Org. Process Res. Dev. 2010, 14, 328
13. Mitchell, A.; Bailey, T. Br. Patent 2 078 718, 1982.
14. Spielmann, W.; Schaeffer, G. DE 3 001 511, 1980.
15. Vallejos, J.-C.; Christidis, Y. EP 0 221 815, 1986.
16. Philip, N. E. Br. Patent 1 576 333, 1976.
17. Vallejos, J.-C.; Legrand, O.; Christidis, Y. Bull. Soc. Chim. Fr. 1997, 134, 101
18. Ronchin, L.; Toniolo, L.; Cavinato, G. Appl. Catal., A 1997, 165, 133
19. Milne, J. E.; Murry, J. A.; King, A.; Larsen, R. D. J. Org. Chem. 2009, 74, 445
20. Corson, B. B.; Dodge, R. A.; Harris, S. A.; Yeaw, J. S. Org. Synth. 1926, 6, 58
21. Bjorsvik, H.-R.; Liguori, L.; Minisci, F. Org. Process Res. Dev. 2000, 4, 534
22. Weist, S.; Kittel, C.; Bischoff, D.; Bister, B.; Pfeifer, V.; Nicholson, G. J.; Wohlleben, W.; Sussmuth, R. D. J. Am. Chem. Soc. 2004, 126, 5942
23. Czaplicki, S.; Kostanecki, S. T. V.; Lampe, V. Ber. Dtsch. Chem. Ges. 1909, 42, 827
24. Aloy, J.; Rabaut, Ch. Bull. Soc. Chim. Fr. 1911, 9, 762
25. Miescher, K.; Billeter, J. R. Helv. Chim. Acta 1939, 22, 601
26. Marvel, C. S.; Hager, F. D.; Caudle, E. C. Org. Synth. 1923, 3, 45
27. Shaw, K. N. F.; Armstrong, M. D.; McMillan, A. J. Org. Chem. 1956, 22, 1149
28. Sugita, S.-I.; Toda, S.; Yoshiyasu, T.; Teraji, T. Mol. Cryst. Liq. Cryst. 1993, 237, 399
29. Dozeman, G. J.; Fiore, P. J.; Puls, T. P.; Walker, J. C. Org. Process Res. Dev. 1997, 1, 137
30. Gordon, P. E.; Fry, A. J. Tetrahedron Lett. 2001, 42, 831
31. Hicks, L. D.; Han, J. K.; Fry, A. J. Tetrahedron Lett. 2000, 41, 7817
32. Harvey, R. G; Leyba, C.; Konieczny, M.; Fu, P. P.; Sukumaran, K. B. J. Org. Chem. 1978, 43, 3423
33. Aramini, A.; Sablone, M. R.; Bianchini, G.; Amore, A.; Fani, M.; Perrone, P.; Dolce, A.; Allegretti, M. Tetrahedron 2009, 65, 2015
34. Platt, K. L.; Oesch, F. J. Org. Chem. 1981, 46, 2601
35. 3: Its application to the synthesis of a potential anticancer agent. Wu, G. G.; Chen, F. X.; LaFrance, D.; Liu, Z.; Greene, S. G.; Wong, Y.-S.; Xie, J. Org. Lett. 2011, 13, 5220
36. Zhou, G.; Zhang, P.; Pan, Y. Tetrahedron 2005, 61, 5671
37. Campbell, N.; McKail, J. J. Am. Chem. Soc. 1948, 1251
38. Cabedo, N.; Andreu, I.; Ramirez de Arellano, M.; Chagraoui, A.; Serrano, A.; Bermejo, A.; Protais, P.; Cortes, D. J. Med. Chem. 2001, 44, 1794
39. Morrow, N.; Ramsden, C.; Sargent, B.; Wallett, C. Tetrahedron 1998, 54, 9603
40. Ito, R.; Umezawa, N.; Higuchi, T. J. Am. Chem. Soc. 2005, 127, 834
41. Biel, J.; Friedman, H.; Leiser, H.; Sprengeler, E. J. Am. Chem. Soc. 1952, 74, 1485
42. Nwokogu, G.; Wong, J.; Greenwood, T.; Wolfe, J. Org. Lett. 2000, 2, 2643
43. Schoenebeck, F.; Murphy, J.; Zhou, S.; Uenoyama, Y.; Miclo, Y.; Tuttle, T. J. Am. Chem. Soc. 2007, 129, 13368
44. McCurdy, A.; Jimenez, L.; Stauffer, D.; Dougherty, D. J. Am. Chem. Soc. 1992, 114, 10314