Transient 2H-phospholes as powerful synthetic intermediates in organophosphorus chemistry

Accounts of Chemical Research

Volumn 37, Issue 12, 2004, Pages 954-960

  Mathey, François ^a,b  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b SORBONNE UNIVERSITÉ   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE DERIVATIVE; ALKADIENE; ALKENE DERIVATIVE; ALKYNE; CYCLOPENTADIENE DERIVATIVE; METAL DERIVATIVE; ORGANOPHOSPHORUS COMPOUND; PHOSPHOLE DERIVATIVE; POLYMER;

ARTICLE; ASYMMETRIC CATALYSIS; CHEMICAL REACTION KINETICS; CYCLOADDITION; ELECTRIC CONDUCTIVITY; PHYSICAL CHEMISTRY; POLYMERIZATION; PROTON TRANSPORT; REACTION ANALYSIS; SYNTHESIS;

EID: 11244309745     PISSN: 00014842     EISSN: None     Source Type: Journal    
DOI: 10.1021/ar030118v     Document Type: Article

References (55)

1. 13C NMR spectroscopy. Tetrahedron Lett. 1987, 28, 5025-5028.
2. Zurmühlen, H.; Regitz, M. Phosphorus compounds with unusual coordination. 25. Cyclopropenylphosphaalkenes, adducts for synthesis of stable 2H-phospholes. J. Organomet. Chem. 1987, 332, C1-C5.
3. Holand, S.; Charrier, C; Mathey, F.; Fischer, J.; Mitschler, A. Stabilization of 2H-phospholes by complexation. A phosphoruscarbon double bond acting as a four-electron donor. J. Am. Chem. Soc. 1984, 706, 826-828.
4. (a) Märkl, G.; Seidl, E. 2-Benzyl-1-phosphaazulene. Angew. Chem., Int. Ed. Engl. 1983, 22, 57-58.
5. (b) Märkl, G.; Reindl, J. 1-Phosphaazulenes. Tetrahedron Lett. 1992, 33, 5495-5498.
6. Märkl, G.; Seidl, E.; Trötsch, I. 1-Methoxy-3-phenyl-2- phosphaazulene: the first synthesis of 2-phosphaazulenes. Angew. Chem., Int. Ed. Engl. 1983, 22, 879-880.
7. Mathey, F.; Mercier, F. The chemistry of 2H-phospholes. C. R. Acad. Sci. Paris, Sér. IIb 1997, 701-716.
8. Original demonstration: Coggon, P.; Engel, J. F.; McPhail, A. T.; Quin, L. D. Molecular structure of 1-benzylphosphole by X-ray analysis. J. Am. Chem. Soc. 1970, 92, 5779-5780.
9. Cyranski, M. K.; Krygowski, T. M.; Katritzky, A. R.; Schleyer, P. v. R. To what extent can aromaticity be defined uniquely? J. Org. Chem. 2002, 67, 1333-1338.
10. Dinadayalane, T. C.; Geetha, K.; Sastry, G. N. Ab initio and density functional theory (DFT) study on [1, 5] sigmatropic rearrangements in pyrroles, phospholes, and siloles and their Diels-Alder reactivities. J. Phys. Chem. A 2003, 107, 5479-5487.
11. Bachrach, S. M. Theoretical studies of the [1,5] sigmatropic hydrogen shift in cyclopentadiene, pyrrole, and phosphole. J. Org. Chem. 1993, 58, 5414-5421.
12. Charier, C.; Bonnard, H.; de Lauzon, G.; Mathey, F. Proton [1,5] shifts in P-unsubstituted 1H-phospholes. Synthesis and chemistry of 2H-phosphole dimers. J. Am. Chem. Soc. 1983, 105, 6871-6877.
13. Mathey, F.; Mercier, F.; Charrier, C.; Fischer, J.; Mitschler, A. Dicoordinated 2H-phospholes as transient intermediates in the reactions of tervalent phospholes at high temperature. One-step synthesis of 1-phosphanorbornadienes and phosphorins from phospholes. J. Am. Chem. Soc. 1981, 103, 4595-4597.
14. Laporte, F.; Mercier, F.; Ricard, L.; Mathey, F. The equilibrium between 1H- and 2H-phospholes: influence of the substitution pattern and scope. Bull. Soc. Chim. Fr. 1993, 130, 843-850.
15. Mathey, F. Unpublished results.
16. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, J. A., Jr.; Vreven, T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Mabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; Pople, J. A. Gaussian 03, revision B.05; Gaussian, Inc.: Pittsburgh, PA, 2003.
17. De Lauzon, G.; Charrier, C.; Bonnard, H.; Mathey, F.; Fischer, J.; Mitschier, A. X-ray crystal structure and Diels-Alder reactivity of the 3,4-dimethyl-2H-phosphole dimmer. J. Chem. Soc., Chem. Commun. 1982, 1272-1273.
18. Dinadayalane, T. C.; Sastry, G. N. Density functional theory study on dimerizations of phospholes. Organometallics 2003, 22, 5526-5533.
19. Deschamps, B.; Ricard, L.; Mathey, F. A new type of chelating biphospholenes. Organometallics 2003, 22, 1356-1357.
20. Charrier, C.; Bonnard, H.; Mathey, F. Synthesis of phosphorins by reaction of 1,2,5-triphenylphosphole with alkynes. J. Org. Chem. 1982, 47, 2376-2379.
21. Mathey, F.; Mercier, F.; Nief, F.; Fischer, J.; Mitschler, A. Thermal tetramerization of 1-phenyl-3,4-dimethylphosphole. An access to 2,2′-biphospholes and to 2,2′-diphosphafulvalene complexes. J. Am. Chem. Soc. 1982, 704, 2077-2079.
22. 4. J. Chem. Soc., Dalton Trans. 1983, 841-845.
23. Bevierre, M.-O.; Mercier, F.; Ricard, L.; Mathey, F. A first step toward the phosphorus analogues of polythiophenes. Angew. Chem., Int. Ed. Engl. 1990, 29, 655-657.
24. Waschbusch, K.; Le Floch, P.; Mathey, F. Combining the chemistry of phospholes and phosphinines. Bull. Soc. Chim. Fr. 1995, 132, 910-919.
25. Bevierre, M.-O.; Mercier, F.; Ricard, L.; Mathey, F. On the mechanism of the thermal tetramerization of phospholes. Bull. Soc. Chim. Fr. 1992, 129, 1-8.
26. Bevierre, M.-O.; Mercier, F.; Mathey, F.; Jutand, A.; Amatore, A. Electrochemical study of 6-units chains containing thiophene and phosphole rings. An evaluation of electronic delocalization along the chain. New J. Chem. 1991, 15, 545-550.
27. Fave, C.; Hissler, M.; Kárpáti, T.; Rault-Berthelot, J.; Deborde, V.; Toupet, L.; Nyulászi, L.; Réau, R. Connecting π-chromophores by σP-P bonds: a new type of assemblies exhibiting exhibiting σ-π conjugation. J. Am. Chem. Soc. 2004, 126, 6058-6063.
28. Laporte, F.; Mercier, F.; Ricard, L.; Mathey, F. Tetraphosphorus macrocycles from phosphole tetramers. J. Am. Chem. Soc. 1994, 116, 3306-3311.
29. Mercier, F.; Laporte, F.; Ricard, L.; Mathey, F.; Schröder, M.; Regitz, M. The use of a ten-membered tetraphosphole macrocycle to increase the lifetime of a palladium catalyst. Angew. Chem., Int. Ed. Engl. 1997, 36, 2364-2366.
30. Toullec, P.; Ricard, L.; Mathey, F. Hetero-Diels-Alder reactions of 2H-phospholes with aldehydes. J. Org. Chem. 2003, 68, 2803-2806.
31. Bachrach, S. M. Ab initio study of the Diels-Alder reaction between phospholes and ethyne. J. Org. Chem. 1994, 59, 5027-5033.
32. Bachrach, S. M.; Perriott, L. M. Theoretical examination of the Diels-Alder reaction of 1,3-butadiene with cyclopentadiene and 2H-phosphole. Can. J. Chem. 1996, 74, 839-850.
33. Robin, F.; Mercier, F.; Ricard, L.; Mathey, F.; Spagnol, M. BIP-NOR: a new, efficient bisphosphine having two chiral, nonracemizable, bridgehead phosphorus centers for use in asymmetric catalysis. Chem.-Eur. J. 1997, 3, 1365-1369.
34. Faitg, T.; Soulié, J.; Lallemand, J.-Y.; Mercier, F.; Mathey, F. Asymmetric isomerisation of a cyclic diene: a comparative study of BINAP and BIPNOR-rhodium(I) catalysts. Tetrahedron 2000, 56, 101-104.
35. Lelièvre, S.; Mercier, F.; Ricard, L.; Mathey, F. Enantiopure 1-phosphanorbornadiene-2-carboxaldehydes. Tetrahedron: Asymmetry 2000, 11, 4601-4608.
36. Mercier, F.; Brebion, F.; Dupont, R.; Mathey, F. 1-Phosphanorbornadiene- imines and amines in enantioselective allylic C- and N-alkylation. Tetrahedron: Asymmetry 2003, 14, 3137-3140.
37. Gilbertson, S. R.; Genov, D. G.; Rheingold, A. L. Synthesis of new bicyclic P-N ligands and their application in asymmetric Pd-catalyzed π-allyl alkylation and Heck reaction. Org. Lett. 2000, 2, 2885-2888.
38. Neibecker, D.; Réau, R. Phosphanorbornadienes as ligands in the transition metal-catalyzed synthesis of fine chemicals. Angew. Chem., Int. Ed. Engl. 1989, 28, 500-501.
39. Herrmann, W. A.; Kohlpaintner, C. W.; Manetsberger, R. B.; Bahrmann, H.; Kottmann, H. Water-soluble metal complexes and catalysts. Part 7. New efficient water-soluble catalysts for two-phase olefin hydroformylation: BINAS-Na, a superlative in propene hydroformylation. J. Mol. Catal. A 1995, 97, 65-72.
40. Mercier, F.; Mathey, F. A new type of water-soluble phosphine for biphasic catalysis. J. Organomet. Chem. 1993, 462, 103-106.
41. Sunderlin, L. S.; Panu, D.; Puranik, D. B.; Ashe, A. J., III; Squires, R. R. Gas-phase properties and reactivities of phospholide and arsolide anions. Organometallics 1994, 13, 4732-4740.
42. Holand, S.; Jeanjean, M.; Mathey, F. A straightforward access to α-functional phospholide ions. Angew. Chem., Int. Ed. Engl. 1997, 36, 98-100.
43. Holand, S.; Maigrot, N.; Charrier, C.; Mathey, F. Simple access to α-functional phospholide ions. 2. Application to the synthesis of 1-methyl-2-pyrrolyl and 2-(diphenylphosphino)-phenyl derivatives. Organometallics 1998, 17, 2996-2999.
44. Frison, G.; Ricard, L.; Mathey, F. Synthesis and X-ray crystal structure analysis of a Cp-substituted phosphaferrocene. Organometallics 2001, 20, 5513-5514.
45. Toullec, P.; Mathey, F. A simple access to 2-acyl- and 2,5-diacylphospholide ions. Synlett 2001, 1977-1979.
46. Carmichael, D.; Mathey, F.; Ricard, L.; Seeboth, N. Synthesis of 2-silyl substituted phospharuthenocenes and an elaboration into the first phospharuthenocene-phosphine. Chem. Commun. 2002, 2976-2977.
47. Melaimi, M.; Ricard, L.; Mathey, F.; Le Floch, P. Synthesis of phosphole-2,5-dicarboxylic acids via a [1, 5]-shift of carbon dioxide around the phosphole nucleus. Org. Lett. 2002, 4, 1245-1247.
48. Carmichael, D.; Klankermayer, J.; Ricard, L.; Seeboth, N. Synthesis and resolution of the planar chirality of ester-functionalised phospharuthenocenes. Chem. Commun. 2004, 1144-1145.
49. See, for example: Mathey, F. Phosphacymantrenes, the first phosphorus heterocycles with a genuine aromatic chemistry. Tetrahedron Lett. 1976, 4155-4158.
50. Mathey, F.; Mitschler, A.; Weiss, R. Phosphaferrocene. J. Am. Chem. Soc. 1977, 99, 3537.
51. Mercier, F.; Holand, S.; Mathey, F. Synthesis and some reactions of a 2,2′-biphospholyl. J. Organomet. Chem. 1986, 316, 271-279.
52. Mercier, F.; Mathey, F. [1,5] Sigmatropic shifts in a 1,4-diphospholylbenzene. Heteroatom Chem. 1990, 1, 187-190.
53. Deschamps, B.; Ricard, L.; Mathey, F. 2-(2′-Pyridyl) phosphaferrocenes and analogues: a new type of chelating ligands with planar chirality and π-acceptor phosphorus centres. J. Organomet. Chem. 1997, 548, 17-22.
54. Sava, X.; Marinetti, A.; Ricard, L.; Mathey, F. Optically active phospholes: synthesis and use as chiral precursors for phosphinidene and phosphaferrocene complexes, Eur. J. Inorg. Chem. 2002, 1657-1665.
55. Mathey, F. Phospha-organic chemistry: panorama and perspectives. Angew. Chem., Int. Ed. 2003, 42, 1578-1604.