Palladium-catalyzed reactions of 1-phenylphospholene-1-oxides with aryl iodides and aryldiazonium salts

Tetrahedron Letters

Volumn 39, Issue 37, 1998, Pages 6707-6710

  Desmazeau, Pascal ^a,b   Legros, Jean Yves ^a   Fiaud, Jean Claude ^a  

^a UNIVERSITÉ PARIS SUD   (France)

^b SANOFI   (France)

Author keywords

Heck reaction; Phospholanes; Phospholenes

Indexed keywords

1 PHENYLPHOSPHOLENE 1 OXIDE; AMMONIUM DERIVATIVE; DIAZONIUM COMPOUND; IODIDE; OXIDE; PALLADIUM; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL REACTION;

EID: 0032505233     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01401-4     Document Type: Article

References (36)

1. [1] Heck RF. in Comprehensive Organic Synthesis, Vol. 4; Trost BM, Fleming I, editors. Oxford: Pergamon Press, 1991: 833-863.
2. [2] De Meijere A, Meyer F.E. Angew. Chem. Int. Ed. Engl. 1994; 33: 2379-2411.
3. [3] Tsuji J. Palladium Reagents and Catalysts - Innovations in Organic Synthesis. Chichester: Wiley, 1995.
4. [4] Malleron JL, Fiaud JC, Legros JY. Handbook of Palladium-Catalyzed Organic Reactions. London: Academic Press, 1997.
5. [5] Larock RC, Gong WH. J. Org. Chem. 1990; 55: 407-408.
6. [6] Zhang HC, Daves GD Jr. Organometallics 1993; 12: 1499-1500.
7. [7] Satoh T, Itaya T, Okuro K, Miura M, Nomura M. J. Org. Chem. 1995; 60: 7267-7271.
8. [8] Hillers S, Sartori S, Reiser O. J. Am. Chem. Soc. 1996; 118: 2087-2088.
9. [9] Hillers S, Reiser O. Chem. Commun. 1996; 2197-2198.
10. [10] Gudmundsson KS, Drach JC, Townsend LB. Tetrahedron Lett. 1996; 37: 6275-6278.
11. [11] Larhed M, Hallberg A. J. Org. Chem. 1996; 61: 9582-9584.
12. [12] Tietze LF, Ferraccioli R. Synlett 1998, 145-146.
13. [13] Hayashi T, Kubo A, Ozawa F. Pure Appl. Chem. 1992; 64: 421-427.
14. [14] Shibasaki M, Boden CDJ, Kojima A. Tetrahedron 1997, 53, 7371-7395 and references herein.
15. [15] Loiseleur O, Meier P, Pfaltz A. Angew. Chem. Int. Ed. Engl. 1996; 35: 200-202.
16. [16] Trabesinger G, Albinati A, Feiken N, Kunz RW, Pregosin PS, Tschoemer M. J. Am. Chem. Soc. 1997; 119: 6315-6323.
17. [17] Hii KK, Claridge TDW, Brown JM. Angew. Chem. Int. Ed. Engl. 1997; 36: 984-987.
18. [18] Loiseleur O, Hayashi M, Schmees N, Pfaltz A Synthesis 1997; 1338-1345.
19. [19] Mehta G, Sengupta S. Tetrahedron Lett. 1996; 37: 8625-8626.
20. [20] Sonesson C, Larhed M, Nyqvist C, Hallberg A. J. Org. Chem. 1996; 61: 4756-4763.
21. [21] Sonesson C, Wilkström H, Smith MW, Svensson K, Carlsson A, Waters N. Bioorg. Med. Chem. Lett. 1997; 7: 241-246.
22. [22] Sengupta S, Bhattacharyya S. Synth. Commun. 1996; 26: 231-236.
23. [23] Moedritzer K, Miller RE. Syn. React Inorg. Metal-Org. Chem. 1977; 4: 311-332.
24. [24] Leconte M, Pagano S, Mutch A, Lefebvre F, Basset JM, Bull. Soc. Chim. Fr. 1995; 132: 1069-1071.
25. [25] Burk MJ, Feaster JE, Harlow RL. Tetrahedron: Asymmetry 1991; 2: 569-592.
26. [26] Fiaud JC, Legros JY. Tetrahedron Lett. 1991; 32: 5089-5092.
27. [27] Vedejs E, Daugulis O, Diver ST. J. Org. Chem. 1996; 61: 430-431.
28. [28] Pietrusiewicz KM, Kuznikowski M, Koprowski M. Tetrahedron: Asymmetry 1993; 4: 2143-2146.
29. [29] Pietrusiewicz KM, Kuznikowski M. Phosphorus, Sulfur, and Silicon 1993; 77: 57-60.
30. [30] Namyslo JC, Kaufmann DE. Chem. Ber. / Recueil 1997; 130: 1327-1331.
31. [31] Aryldiazonium tetrafluoroborates were prepared according to: Roe A. Org. React. 1949; 5: 193-228.
32. [32] Darses S, Jeffery T, Genêt JP, Brayer JL, Demoute JP. Tetrahedron Lett. 1996; 37: 3857-3860 and references herein.
33. [33] Darses S, Genêt JP, Brayer JL, Demoute JP. Tetrahedron Lett. 1997; 38: 4393-4396.
34. [34] Sengupta S, Bhattacharyya S, Sadhukhan SK. J. Chem. Soc., Perkin Trans. 1 1998; 275-277.
35. [35] Sengupta S, Sadhukhan SK, Bhattacharyya S, Guha J. J. Chem. Soc., Perkin Trans. 1 1998; 407-410.
36. [36] Pietrusiewicz KM, Zablocka M. Chem. Rev. 1994; 94: 1375-1411.