Versatile palladium-catalyzed arylation of organomanganese chlorides by aryl bromides

Journal of Organometallic Chemistry

Volumn 624, Issue 1-2, 2001, Pages 376-379

  Riguet, Eric ^b   Alami, Mouâd ^a,b   Cahiez, Gérard ^b  

^a UNIVERSITÉ PARIS SUD   (France)

^b Lab Synt Organique Selective C   (France)

Author keywords

Aryl bromides; Arylation; Cross coupling reactions; Organomanganese reagents

Indexed keywords

EID: 0001121560     PISSN: 0022328X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0022-328X(00)00891-3     Document Type: Article

References (14)

1. E. Riguet, M. Alami, G. Cahiez, Tetrahedron Lett. 38 (1997) 4397.
2. For recent reviews about the transition metal-catalyzed aryl-aryl coupling reactions see: (a) S.P. Stanforth, Tetrahedron 54 (1998) 263-303. (b) F. Diederich, P.J. Stang (Eds.), Metal-Catalyzed Cross-Coupling Reactions, Wiley-VCH, New York, 1998.
3. For recent reviews about the transition metal-catalyzed aryl-aryl coupling reactions see: (a) S.P. Stanforth, Tetrahedron 54 (1998) 263-303. (b) F. Diederich, P.J. Stang (Eds.), Metal-Catalyzed Cross-Coupling Reactions, Wiley-VCH, New York, 1998.
4. 4 and the solvents were removed in vacuo. Pure unsymmetrical biaryl was isolated by simple filtration through silica gel.
5. For the preparation of triflates see: P.J. Stang, M. Hanack, L.R. Subramanian, Synthesis (1982) 85-126. For cross-coupling reactions from aryl triflates, see for instances: (a) T. Kamikawa, T. Hayashi, Synlett (1997) 163-64. (b) P.G. Ciattini, E. Morera, G. Ortar, Tetrahedron Lett. 33 (1992) 4815-18.
6. For the preparation of triflates see: P.J. Stang, M. Hanack, L.R. Subramanian, Synthesis (1982) 85-126. For cross-coupling reactions from aryl triflates, see for instances: (a) T. Kamikawa, T. Hayashi, Synlett (1997) 163-64. (b) P.G. Ciattini, E. Morera, G. Ortar, Tetrahedron Lett. 33 (1992) 4815-18.
7. For the preparation of triflates see: P.J. Stang, M. Hanack, L.R. Subramanian, Synthesis (1982) 85-126. For cross-coupling reactions from aryl triflates, see for instances: (a) T. Kamikawa, T. Hayashi, Synlett (1997) 163-64. (b) P.G. Ciattini, E. Morera, G. Ortar, Tetrahedron Lett. 33 (1992) 4815-18.
8. See Ref. [2] and references quoted herein. Until now, few efficient procedures were reported to prepare hindered diaryls, see for instances; from arylboronic acids: (a) A.F. Littke, C. Dal, G.C. Fu, J. Am. Chem. Soc. 122 (2000) 4020-4028. (b) T. Watanabe, N. Miyaura, A. Suzuki, Synlett (1992) 207-210; from arylstannanes: J.M. Saá, O. Martorell, J. Org. Chem. 58 (1993) 1963- 1966.
9. See Ref. [2] and references quoted herein. Until now, few efficient procedures were reported to prepare hindered diaryls, see for instances; from arylboronic acids: (a) A.F. Littke, C. Dal, G.C. Fu, J. Am. Chem. Soc. 122 (2000) 4020-4028. (b) T. Watanabe, N. Miyaura, A. Suzuki, Synlett (1992) 207-210; from arylstannanes: J.M. Saá, O. Martorell, J. Org. Chem. 58 (1993) 1963- 1966.
10. See Ref. [2] and references quoted herein. Until now, few efficient procedures were reported to prepare hindered diaryls, see for instances; from arylboronic acids: (a) A.F. Littke, C. Dal, G.C. Fu, J. Am. Chem. Soc. 122 (2000) 4020-4028. (b) T. Watanabe, N. Miyaura, A. Suzuki, Synlett (1992) 207-210; from arylstannanes: J.M. Saá, O. Martorell, J. Org. Chem. 58 (1993) 1963-1966.
11. 2(dppf) as a catalyst allows us to avoid or to limit the β-hydrogen elimination when an alkylmetal having eliminable β-hydrogen atoms is used. See for instance: T. Hayashi, M. Konishi, Y. Kobori, M. Kumada, T. Higuchi, K. Hirotsu, J. Am. Chem. Soc. 106 (1984) 158-163.
12. For reviews on the preparation and the reactivity of organomanganese reagents see: (a) G. Cahiez, Butyl manganese chloride, in: L. Paquette (Ed.), Encyclopedia of Reagents for Organic Synthesis, vol. 2, Wiley, Chichester, 1995, pp. 925-928. (b) G. Cahiez, Manganese(II) chloride, in: L. Paquette, (Ed.), Encyclopedia of Reagents for Organic Synthesis, vol. 5, Wiley, Chichester, 1995, pp. 3227-3228. G. Cahiez, An. Quim. 91 (1995) 561-578.
13. For reviews on the preparation and the reactivity of organomanganese reagents see: (a) G. Cahiez, Butyl manganese chloride, in: L. Paquette (Ed.), Encyclopedia of Reagents for Organic Synthesis, vol. 2, Wiley, Chichester, 1995, pp. 925-928. (b) G. Cahiez, Manganese(II) chloride, in: L. Paquette, (Ed.), Encyclopedia of Reagents for Organic Synthesis, vol. 5, Wiley, Chichester, 1995, pp. 3227-3228. G. Cahiez, An. Quim. 91 (1995) 561-578.
14. For reviews on the preparation and the reactivity of organomanganese reagents see: (a) G. Cahiez, Butyl manganese chloride, in: L. Paquette (Ed.), Encyclopedia of Reagents for Organic Synthesis, vol. 2, Wiley, Chichester, 1995, pp. 925-928. (b) G. Cahiez, Manganese(II) chloride, in: L. Paquette, (Ed.), Encyclopedia of Reagents for Organic Synthesis, vol. 5, Wiley, Chichester, 1995, pp. 3227-3228. G. Cahiez, An. Quim. 91 (1995) 561-578.