Oxidative transition-metal-free cross-coupling of secondary phosphine chalcogenides and alcohols or phenols: A facile, expedient synthesis of phosphinochalcogenoic O-esters

Synthesis

Volumn , Issue 22, 2011, Pages 3723-3729

  Gusarova, Nina K ^a   Volkov, Pavel A ^a   Ivanova, Nina I ^a   Larina, Ludmila I ^a   Trofimov, Boris A ^a  

^a A E FAVORSKY IRKUTSK INSTITUTE OF CHEMISTRY   (Russian Federation)

Author keywords

alcohols; phenols; phosphinochalcogenoic O esters; secondary phosphine chalcogenides

Indexed keywords

CROSS COUPLING REACTIONS; CROSS-COUPLINGS; PHOSPHINOCHALCOGENOIC O-ESTERS; SECONDARY PHOSPHINES;

CHALCOGENIDES; ESTERIFICATION; ESTERS; PHOSPHORUS COMPOUNDS; SYNTHESIS (CHEMICAL); TRANSITION METALS;

PHENOLS;

ALCOHOL; BIS(2 PHENYLETHYL)PHOSPHINIC O PHENYL ESTER; BIS(2 PHENYLETHYL)PHOSPHINOSELENOIC O (TETRAHYDRO 2 FURYL)METHYL ESTER; BIS(2 PHENYLETHYL)PHOSPHINOSELENOIC O 1 NAPHTHYL ESTER; BIS(2 PHENYLETHYL)PHOSPHINOSELENOIC O 2 (DIMETHYLAMINO)ETHYL ESTER; BIS(2 PHENYLETHYL)PHOSPHINOSELENOIC O 2 FURYLMETHYL ESTER; BIS(2 PHENYLETHYL)PHOSPHINOSELENOIC O ISOPROPYL ESTER; BIS(2 PHENYLETHYL)PHOSPHINOSELENOIC O METHYL ESTER; BIS(2 PHENYLETHYL)PHOSPHINOSELENOIC O PHENYL ESTER; BIS(2 PHENYLETHYL)PHOSPHINOSELENOIC O PROP 2 YNYL ESTER; BIS(2 PHENYLETHYL)PHOSPHINOTHIOIC O 1 NAPHTHYL ESTER; BIS(2 PHENYLETHYL)PHOSPHINOTHIOIC O ETHYL ESTER; BIS(2 PHENYLETHYL)PHOSPHINOTHIOIC O METHYL ESTER; BIS(2 PHENYLETHYL)PHOSPHINOTHIOIC O PHENYL ESTER; BIS(2 PHENYLPROPYL)PHOSPHINOSELENOIC O 1 NAPHTHYL ESTER; BIS(2 PHENYLPROPYL)PHOSPHINOSELENOIC O 2 (DIMETHYLAMINO)ETHYL ESTER; BIS(2 PHENYLPROPYL)PHOSPHINOSELENOIC O METHYL ESTER; CARBON TETRACHLORIDE; CHALCOGEN; DIPHENYLPHOSPHINIC O PHENYL ESTER; DIPHENYLPHOSPHINOSELENOIC O 1 NAPHTHYL ESTER; METAL; PHENOL; PHOSPHINE CHALCOGENIDE DERIVATIVE; PHOSPHINOCHALCOGENOIC O ESTER; TRIETHYLAMINE; UNCLASSIFIED DRUG;

ARTICLE; CROSS COUPLING REACTION; DRUG STRUCTURE; DRUG SYNTHESIS; OXIDATION; PHASE TRANSITION;

EID: 80755135365     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0030-1260227     Document Type: Article

References (79)

1. Bateson J H., Robins A M., Southgate R, J. Chem. Soc., Perkin Trans. 1 1991 29
2. Tawata S, Taira S, Kobamoto N, Ishihara M, Toyama S, Biosci. Biotechnol. Biochem. 1996 60 1643
3. Beznosko B K., Usanova V M., Zhuravleva L V., Baulin V E., Yarkevich A N., Syundyukova V Ch, Tsvetkov E N., Pharm. Chem. J. (Engl. Transl.) 1997 31 638
4. Li Y, Aubert S D., Maes E G., Raushel F M., J. Am. Chem. Soc. 2004 126 8888
5. Ravaschino E L., Docampo R, Rodriguez J B., J. Med. Chem. 2006 49 426
6. Vassiliou S, Xeilari M, Yiotakis A, Grembecka J, Paweczak M, Kafarski P, Mucha A, Bioorg. Med. Chem. 2007 15 3187
7. Yang Y, Coward J K., J. Org. Chem. 2007 72 5748
8. Klimek-Ochab M, Ymaczyk-Duda E, Brzeziska-Rodak M, Majewska P, Lejczak B, Tetrahedron: Asymmetry 2008 19 450
9. Majewska P, Doskocz M, Lejczak B, Kafarski P, Tetrahedron: Asymmetry 2009 20 1568
10. Vassiliou S, Kosikowska P, Grabowiecka A, Yiotakis A, Kafarski P, Berlicki, J. Med. Chem. 2010 53 5597
11. Alexandre F.-R, Amador A, Bot S, Caillet C, Convard T, Jakubik J, Musiu C, Poddesu B, Vargiu L, Liuzzi M, Roland A, Seifer M, Standring D, Storer R, Dousson C B., J. Med. Chem. 2011 54 392
12. Abbas S, Beagley B, Godfrey S M., Kelly D G., McAuliffe C A., Pritchard R G., J. Chem. Soc., Dalton Trans. 1992 1915
13. Lukin O, Vysotsky M O., Kalchenko V I., J. Phys. Org. Chem. 2001 14 468
14. Cauzzi D, Graiff C, Pattacini R, Predieri G, Tiripicchio A, Kahlal S, Saillard J.-Y, Eur. J. Inorg. Chem. 2004 1063
15. Eisler D J., Puddephatt R J., Inorg. Chem. 2006 45 7295
16. Reger D L., Semeniuc R F., Smith M D., Dalton Trans. 2008 2253
17. Adati R D., Davolos M R., Jafelicci M, Lima S A. M., Viegas C, Phys. Status Solidi C 2009 6 542
18. Li C, Pattacini R, Braunstein P, Inorg. Chim. Acta 2010 363 4337
19. Kozlov V A., Aleksanyan D V., Nelyubina Y V., Lyssenko K A., Vasilev A A., Petrovskii P V., Odinets I L., Organometallics 2010 29 2054
20. Aleksanyan D V., Kozlov V A., Nelyubina Y V., Lyssenko K A., Puntus L N., Gutsul E I., Shepel N E., Vasilev A A., Petrovskii P V., Odinets I L., Dalton Trans. 2011 40 1535
21. Kozlov V A., Aleksanyan D V., Vasilev A A., Petrovskii P V., Odinets I L., Phosphorus, Sulfur Silicon Relat. Elem. 2011 186 626
22. Noetzel S, Jastrow H, Uebe R, US 4111900 1978, Howell B A., Carter K E., J. Therm. Anal. Calorim. 2010 102 493
23. Xu K, Liu X, Tang B, Yang G, Yang Y, An L, Chem. Eur. J. 2007 13 1411
24. Xu K, Liu X, Tang B, ChemBioChem 2007 8 453
25. Tang B, Ding B, Xu K, Tong L, Chem. Eur. J. 2009 15 3147
26. Chen B.-Q, Kameyama A, Nishikubo T, J. Polym. Sci., Part A: Polym. Chem. 1999 37 1009
27. Clive D L. J., Kang S, J. Org. Chem. 2001 66 6083
28. Dunne K S., Bisaro F, Odell B, Paris J.-M, Gouverneur V, J. Org. Chem. 2005 70 10803
29. Um I.-H, Shin Y.-H, Han J.-Y, Mishima M, J. Org. Chem. 2006 71 7715
30. Um I.-H, Akhtar K, Shin Y.-H, Han J.-Y, J. Org. Chem. 2007 72 3823
31. Cheruku P, Gohil S, Andersson P G., Org. Lett. 2007 9 1659
32. Harvey J S., Malcolmson S J., Dunne K S., Meek S J., Thompson A L., Schrock R R., Hoveyda A H., Gouverneur V, Angew. Chem. Int. Ed. 2009 48 762
33. Lam K, Markó I E., Org. Lett. 2011 13 406
34. Stuebe C, LeSuer W M., Norman G R., J. Am. Chem. Soc. 1955 77 3526
35. Balakrishna M S., Panda R, Mague J T., J. Chem. Soc., Dalton Trans. 2002 4617
36. Marosi G, Toldy A, Parlagh G, Nagy Z, Ludányi K, Anna P, Keglevich G, Heteroat. Chem. 2002 13 126
37. Balakrishna M S., George P P., Mobin S M., Polyhedron 2005 24 475
38. Kimura T, Murai T, J. Org. Chem. 2005 70 952
39. Baysal A, Aydemir M, Durap F, Gümgüm B, Özkar S, Yildirim T L., Polyhedron 2007 26 3373
40. Williams D B. G., Netshiozwi T E., Tetrahedron 2009 65 9973
41. Zhou Y, Wang G, Saga Y, Shen R, Goto M, Zhao Y, Han L.-B, J. Org. Chem. 2010 75 7924
42. Hassner A, Stumer C, In Tetrahedron Organic Chemistry Series Vol. 22 Elsevier New York 2002 443
43. Rauhut M M., Currier H A., J. Org. Chem. 1961 26 4628
44. Peters G, J. Org. Chem. 1962 27 2198
45. Wang G, Shen R, Xu Q, Goto M, Zhao Y, Han L.-B, J. Org. Chem. 2010 75 3890
46. See, for example:, Bravo-Altamirano K, Huang Z, Montchamp J.-L, Tetrahedron 2005 61 6315
47. Alonso F, Beletskaya I P., Yus M, Tetrahedron 2008 64 3047
48. He C.-Y, Fan S, Zhang X, J. Am. Chem. Soc. 2010 132 12850
49. Cahiez G, Moyeux A, Chem. Rev. 2010 110 1435
50. Ishizuka K, Seike H, Hatakeyama T, Nakamura M, J. Am. Chem. Soc. 2010 132 13117
51. Zhou Z.-Z, Liu F.-S, Shen D.-S, Tan C, Luo L.-Y, Inorg. Chem. Commun. 2011 14 659
52. Kitamura M, Sakata R, Okauchi T, Tetrahedron Lett. 2011 52 1931
53. Zhong R, Wang Y.-N, Guo X.-Q, Hou X.-F, J. Organomet. Chem. 2011 696 1703
54. He Y, Cai C, Catal. Commun. 2011 12 678
55. Du Z, Zhou W, Wang F, Wang J.-X, Tetrahedron 2011 67 4914
56. Perez F, Minatti A, Org. Lett. 2011 13 1984
57. Anokhin M V., Averin A D., Buryak A K., Beletskaya I P., Mendeleev Commun. 2011 21 132
58. Beletskaya I P., Ananikov V P., Chem. Rev. 2011 111 1596
59. Huang Y.-B, Yang C.-T, Yi J, Deng X.-J, Fu Y, Liu L, J. Org. Chem. 2011 76 800
60. See, for example:, Kienle M, Knochel P, Org. Lett. 2010 12 2702
61. Petrovi Z D., Simijonovi D, Petrovi V P., Markovi S, J. Mol. Catal. A: Chem. 2010 327 45
62. Ren G, Cui X, Yang E, Yang F, Wu Y, Tetrahedron 2010 66 4022
63. Zhou J, Li X, Sun H, J. Organomet. Chem. 2010 695 297
64. Srinivas P, Srinivas K, Likhar P R., Sridhar B, Mohan K V., Bhargava S, Kantam M L., J. Organomet. Chem. 2011 696 795
65. Wang J, Song G, Peng Y, Tetrahedron Lett. 2011 52 1477
66. Tanaka M, Hikawa H, Yokoyama Y, Tetrahedron 2011 67 5897
67. Zhang T, Gao X, Wood H B., Tetrahedron Lett. 2011 52 311
68. Nguyen V T. H., Appel B, Langer P, Tetrahedron 2006 62 7674
69. Maliska-Solich J, Kukowka S, Markowski P, React. Funct. Polym. 2008 68 544
70. Trujillo A, Fuentealba M, Carrillo D, Manzur C, Hamon J.-R, J. Organomet. Chem. 2009 694 1435
71. Venkatraman S, Li C.-J, Tetrahedron Lett. 2000 41 4831
72. Schaarschmidt D, Lang H, Organometallics 2010 29 4196
73. Chen W, Wang M, Li P, Wang L, Tetrahedron 2011 67 5913
74. Arbuzova S N., Gusarova N K., Trofimov B A., ARKIVOC 2006 (v) 12
75. Trofimov B A., Gusarova N K., Mendeleev Commun. 2009 19 295
76. Malysheva S F., Artemev A V., Gusarova N K., Timokhin B V., Tatarinova A A., Trofimov B A., Russ. J. Gen. Chem. (Engl. Transl.) 2009 79 1617
77. Armarego W L. E., Chai C L. L., Purification of Laboratory Chemicals 5th ed. Elsevier Science New York 2003
78. Maier L, Helv. Chim. Acta 1966 49 1000
79. Berlin K D., Austin T N., Nagadhushanam M, J. Org. Chem. 1965 30 1267