Palladium-Catalyzed Regioselective Mono- and Diarylation Reactions of 2-Phenylphenols and Naphthols with Aryl Halides

Angewandte Chemie (International Edition in English)

Volumn 36, Issue 16, 1997, Pages 1740-1742

  Satoh, Tetsuya ^a   Kawamura, Yuichiro ^a   Miura, Masahiro ^a   Nomura, Masakatsu ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

Biaryls; C C coupling; Homogeneous catalysis; O ligands; Palladium

Indexed keywords

EID: 0030776292     PISSN: 05700833     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.199717401     Document Type: Article

References (30)

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5. Recently, the following novel palladium-catalyzed reactions involving C-H bond activation have been reported: di-[2a,b] and triarylations[2c,d] of norbornene, and di-[2e] and trimerizations [2f] of aryl halides. a) M. Catellani, G. P. Chiusoli, J. Organomet. Chem. 1985, 286, C13-C16; b) ibid. 1991, 407, C30-C33; c) O. Reiser, M. Weber, A. de Meijere, Angew. Chem. 1989, 101, 1071-1072; Angew. Chem. Int. Ed. Engl. 1989, 28,1 037-1038; d) K. Albrecht, O. Reiser, M. Weber, B. Knieriem, A. de Meijere, Tetrahedron 1994, 50, 383-401; e) G. Dyker, Angew. Chem. 1992, 104, 1079-1081; Angew. Chem. Int. Ed. Engl. 1992, 31, 1023-1025; f) ibid. 1994, 106, 117-119 and 1994, 33, 103-105.
6. Recently, the following novel palladium-catalyzed reactions involving C-H bond activation have been reported: di-[2a,b] and triarylations[2c,d] of norbornene, and di-[2e] and trimerizations [2f] of aryl halides. a) M. Catellani, G. P. Chiusoli, J. Organomet. Chem. 1985, 286, C13-C16; b) ibid. 1991, 407, C30-C33; c) O. Reiser, M. Weber, A. de Meijere, Angew. Chem. 1989, 101, 1071-1072; Angew. Chem. Int. Ed. Engl. 1989, 28,1 037-1038; d) K. Albrecht, O. Reiser, M. Weber, B. Knieriem, A. de Meijere, Tetrahedron 1994, 50, 383-401; e) G. Dyker, Angew. Chem. 1992, 104, 1079-1081; Angew. Chem. Int. Ed. Engl. 1992, 31, 1023-1025; f) ibid. 1994, 106, 117-119 and 1994, 33, 103-105.
7. Recently, the following novel palladium-catalyzed reactions involving C-H bond activation have been reported: di-[2a,b] and triarylations[2c,d] of norbornene, and di-[2e] and trimerizations [2f] of aryl halides. a) M. Catellani, G. P. Chiusoli, J. Organomet. Chem. 1985, 286, C13-C16; b) ibid. 1991, 407, C30-C33; c) O. Reiser, M. Weber, A. de Meijere, Angew. Chem. 1989, 101, 1071-1072; Angew. Chem. Int. Ed. Engl. 1989, 28,1 037-1038; d) K. Albrecht, O. Reiser, M. Weber, B. Knieriem, A. de Meijere, Tetrahedron 1994, 50, 383-401; e) G. Dyker, Angew. Chem. 1992, 104, 1079-1081; Angew. Chem. Int. Ed. Engl. 1992, 31, 1023-1025; f) ibid. 1994, 106, 117-119 and 1994, 33, 103-105.
8. Recently, the following novel palladium-catalyzed reactions involving C-H bond activation have been reported: di-[2a,b] and triarylations[2c,d] of norbornene, and di-[2e] and trimerizations [2f] of aryl halides. a) M. Catellani, G. P. Chiusoli, J. Organomet. Chem. 1985, 286, C13-C16; b) ibid. 1991, 407, C30-C33; c) O. Reiser, M. Weber, A. de Meijere, Angew. Chem. 1989, 101, 1071-1072; Angew. Chem. Int. Ed. Engl. 1989, 28,1 037-1038; d) K. Albrecht, O. Reiser, M. Weber, B. Knieriem, A. de Meijere, Tetrahedron 1994, 50, 383-401; e) G. Dyker, Angew. Chem. 1992, 104, 1079-1081; Angew. Chem. Int. Ed. Engl. 1992, 31, 1023-1025; f) ibid. 1994, 106, 117-119 and 1994, 33, 103-105.
9. Recently, the following novel palladium-catalyzed reactions involving C-H bond activation have been reported: di-[2a,b] and triarylations[2c,d] of norbornene, and di-[2e] and trimerizations [2f] of aryl halides. a) M. Catellani, G. P. Chiusoli, J. Organomet. Chem. 1985, 286, C13-C16; b) ibid. 1991, 407, C30-C33; c) O. Reiser, M. Weber, A. de Meijere, Angew. Chem. 1989, 101, 1071-1072; Angew. Chem. Int. Ed. Engl. 1989, 28,1 037-1038; d) K. Albrecht, O. Reiser, M. Weber, B. Knieriem, A. de Meijere, Tetrahedron 1994, 50, 383-401; e) G. Dyker, Angew. Chem. 1992, 104, 1079-1081; Angew. Chem. Int. Ed. Engl. 1992, 31, 1023-1025; f) ibid. 1994, 106, 117-119 and 1994, 33, 103-105.
10. Recently, the following novel palladium-catalyzed reactions involving C-H bond activation have been reported: di-[2a,b] and triarylations[2c,d] of norbornene, and di-[2e] and trimerizations [2f] of aryl halides. a) M. Catellani, G. P. Chiusoli, J. Organomet. Chem. 1985, 286, C13-C16; b) ibid. 1991, 407, C30-C33; c) O. Reiser, M. Weber, A. de Meijere, Angew. Chem. 1989, 101, 1071-1072; Angew. Chem. Int. Ed. Engl. 1989, 28,1 037-1038; d) K. Albrecht, O. Reiser, M. Weber, B. Knieriem, A. de Meijere, Tetrahedron 1994, 50, 383-401; e) G. Dyker, Angew. Chem. 1992, 104, 1079-1081; Angew. Chem. Int. Ed. Engl. 1992, 31, 1023-1025; f) ibid. 1994, 106, 117-119 and 1994, 33, 103-105.
11. Recently, the following novel palladium-catalyzed reactions involving C-H bond activation have been reported: di-[2a,b] and triarylations[2c,d] of norbornene, and di-[2e] and trimerizations [2f] of aryl halides. a) M. Catellani, G. P. Chiusoli, J. Organomet. Chem. 1985, 286, C13-C16; b) ibid. 1991, 407, C30-C33; c) O. Reiser, M. Weber, A. de Meijere, Angew. Chem. 1989, 101, 1071-1072; Angew. Chem. Int. Ed. Engl. 1989, 28,1 037-1038; d) K. Albrecht, O. Reiser, M. Weber, B. Knieriem, A. de Meijere, Tetrahedron 1994, 50, 383-401; e) G. Dyker, Angew. Chem. 1992, 104, 1079-1081; Angew. Chem. Int. Ed. Engl. 1992, 31, 1023-1025; f) ibid. 1994, 106, 117-119 and 1994, 33, 103-105.
12. Recently, the following novel palladium-catalyzed reactions involving C-H bond activation have been reported: di-[2a,b] and triarylations[2c,d] of norbornene, and di-[2e] and trimerizations [2f] of aryl halides. a) M. Catellani, G. P. Chiusoli, J. Organomet. Chem. 1985, 286, C13-C16; b) ibid. 1991, 407, C30-C33; c) O. Reiser, M. Weber, A. de Meijere, Angew. Chem. 1989, 101, 1071-1072; Angew. Chem. Int. Ed. Engl. 1989, 28,1 037-1038; d) K. Albrecht, O. Reiser, M. Weber, B. Knieriem, A. de Meijere, Tetrahedron 1994, 50, 383-401; e) G. Dyker, Angew. Chem. 1992, 104, 1079-1081; Angew. Chem. Int. Ed. Engl. 1992, 31, 1023-1025; f) ibid. 1994, 106, 117-119 and 1994, 33, 103-105.
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18. Previous syntheses of 1,2,3-triarylbenzenes required multistep reactions: e.g. a) T. Sato, S. Shimada, K. Hata, Bull. Chem. Soc. Jpn. 1971, 44, 2484-2490; b) S. Ozasa, Y. Fujioka, J. Kikutake, E. Ibuki, Chem. Pharm. Bull. 1983, 31, 1572-1581.
19. Previous syntheses of 1,2,3-triarylbenzenes required multistep reactions: e.g. a) T. Sato, S. Shimada, K. Hata, Bull. Chem. Soc. Jpn. 1971, 44, 2484-2490; b) S. Ozasa, Y. Fujioka, J. Kikutake, E. Ibuki, Chem. Pharm. Bull. 1983, 31, 1572-1581.
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