5,5′-Bicalix[4]arene: The Bridgeless Prototype of Double Calix[4]arenes of the "Head-to-Head" Type

Angewandte Chemie - International Edition

Volumn 37, Issue 1-2, 1998, Pages 166-169

  Neri, Placido ^a   Bottino, Alessandra ^a   Cunsolo, Francesca ^a   Piattelli, Mario ^a   Gavuzzo, Enrico ^a  

^a CNR   (Italy)

Author keywords

Biaryls; Calixarenes; Configuration determination; Host guest chemistry; Macrocycles

Indexed keywords

EID: 0031905296     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3773(19980202)37:1/2<166::AID-ANIE166>3.0.CO;2-P     Document Type: Article

References (41)

1. Review on calixarenes: V. Böhmer, Angew. Chem. 1995, 107, 785; Angew. Chem. Int. Ed Engl. 1995, 34, 713.
2. Review on calixarenes: V. Böhmer, Angew. Chem. 1995, 107, 785; Angew. Chem. Int. Ed Engl. 1995, 34, 713.
3. Review on double calixarenes: Z. Asfari, J. Weiss, J. Vicens, Synlett 1993, 719.
4. 2Ar group: a) O. Aleksiuk. S. E. Biali, J. Org. Chem. 1996, 61, 5670. b) Calixarenes: A Versatile Class of Macrocyclic Compounds (Eds.: J. Vicens, V. Böhmer), Kluwer, Dordrecht, 1991, p. 60.
5. 2Ar group: a) O. Aleksiuk. S. E. Biali, J. Org. Chem. 1996, 61, 5670. b) Calixarenes: A Versatile Class of Macrocyclic Compounds (Eds.: J. Vicens, V. Böhmer), Kluwer, Dordrecht, 1991, p. 60.
6. Special cases of multiple calixarenes are Böhmer's "annelated" calixarenes, in which the two macrocycles share two adjacent phenol rings: V. Böhmer, R. Dörrenbächer, M. Frings, M. Heydenreich, D. de Paoli, W. Vogt, G. Ferguson, I. Thondorf, J. Org. Chem. 1996, 61, 549.
7. Recent examples not included in ref. [1, 2]: O. Struck, L. A. J. Chrisstoffels, R. J. W. Lugtenberg, W. Verboom, G. J. van Hummel, S. Harkema, D. N. Reinhoudt, J. Org. Chem. 1997, 62, 2487; J. A. Perez-Adelmar, H. Abraham, C. Sanchez, K. Rissanen, P. Prados, J. de Mendoza, Angew. Chem. 1996, 108, 1088; Angew. Chem. Int. Ed. Engl. 1996, 55, 1009; M. A. McKervey, M. Pitarch, J. Chem. Soc. Chem. Commun, 1996, 1689; A. Siepen, A. Zett, F. Vögtle, Liebigs Ann. 1996, 757; P. Lhotak, S. Shinkai, Tetrahedron Lett. 1996, 37, 645; P. Lhotak, M. Kawaguchi, A. Ikeda, S. Shinkai. Tetrahedron 1996, 52, 12399; A. Arduini, S. Fanni, G. Manfredi, A. Pochini, R. Ungaro, A. R. Sicuri, F. Ugozzoli, J. Org. Chem. 1995, 60, 1448; F. Ohseto, S. Shinkai, J. Chem. Soc. Perkin Trans. 2 1995, 1103; H. Ross, U. Lüning, Angew. Chem. 1995, 107, 2723; Angew. Chem. Int. Ed. Engl. 1995, 34, 2555.
8. Recent examples not included in ref. [1, 2]: O. Struck, L. A. J. Chrisstoffels, R. J. W. Lugtenberg, W. Verboom, G. J. van Hummel, S. Harkema, D. N. Reinhoudt, J. Org. Chem. 1997, 62, 2487; J. A. Perez-Adelmar, H. Abraham, C. Sanchez, K. Rissanen, P. Prados, J. de Mendoza, Angew. Chem. 1996, 108, 1088; Angew. Chem. Int. Ed. Engl. 1996, 55, 1009; M. A. McKervey, M. Pitarch, J. Chem. Soc. Chem. Commun, 1996, 1689; A. Siepen, A. Zett, F. Vögtle, Liebigs Ann. 1996, 757; P. Lhotak, S. Shinkai, Tetrahedron Lett. 1996, 37, 645; P. Lhotak, M. Kawaguchi, A. Ikeda, S. Shinkai. Tetrahedron 1996, 52, 12399; A. Arduini, S. Fanni, G. Manfredi, A. Pochini, R. Ungaro, A. R. Sicuri, F. Ugozzoli, J. Org. Chem. 1995, 60, 1448; F. Ohseto, S. Shinkai, J. Chem. Soc. Perkin Trans. 2 1995, 1103; H. Ross, U. Lüning, Angew. Chem. 1995, 107, 2723; Angew. Chem. Int. Ed. Engl. 1995, 34, 2555.
9. Recent examples not included in ref. [1, 2]: O. Struck, L. A. J. Chrisstoffels, R. J. W. Lugtenberg, W. Verboom, G. J. van Hummel, S. Harkema, D. N. Reinhoudt, J. Org. Chem. 1997, 62, 2487; J. A. Perez-Adelmar, H. Abraham, C. Sanchez, K. Rissanen, P. Prados, J. de Mendoza, Angew. Chem. 1996, 108, 1088; Angew. Chem. Int. Ed. Engl. 1996, 55, 1009; M. A. McKervey, M. Pitarch, J. Chem. Soc. Chem. Commun, 1996, 1689; A. Siepen, A. Zett, F. Vögtle, Liebigs Ann. 1996, 757; P. Lhotak, S. Shinkai, Tetrahedron Lett. 1996, 37, 645; P. Lhotak, M. Kawaguchi, A. Ikeda, S. Shinkai. Tetrahedron 1996, 52, 12399; A. Arduini, S. Fanni, G. Manfredi, A. Pochini, R. Ungaro, A. R. Sicuri, F. Ugozzoli, J. Org. Chem. 1995, 60, 1448; F. Ohseto, S. Shinkai, J. Chem. Soc. Perkin Trans. 2 1995, 1103; H. Ross, U. Lüning, Angew. Chem. 1995, 107, 2723; Angew. Chem. Int. Ed. Engl. 1995, 34, 2555.
10. Recent examples not included in ref. [1, 2]: O. Struck, L. A. J. Chrisstoffels, R. J. W. Lugtenberg, W. Verboom, G. J. van Hummel, S. Harkema, D. N. Reinhoudt, J. Org. Chem. 1997, 62, 2487; J. A. Perez-Adelmar, H. Abraham, C. Sanchez, K. Rissanen, P. Prados, J. de Mendoza, Angew. Chem. 1996, 108, 1088; Angew. Chem. Int. Ed. Engl. 1996, 55, 1009; M. A. McKervey, M. Pitarch, J. Chem. Soc. Chem. Commun, 1996, 1689; A. Siepen, A. Zett, F. Vögtle, Liebigs Ann. 1996, 757; P. Lhotak, S. Shinkai, Tetrahedron Lett. 1996, 37, 645; P. Lhotak, M. Kawaguchi, A. Ikeda, S. Shinkai. Tetrahedron 1996, 52, 12399; A. Arduini, S. Fanni, G. Manfredi, A. Pochini, R. Ungaro, A. R. Sicuri, F. Ugozzoli, J. Org. Chem. 1995, 60, 1448; F. Ohseto, S. Shinkai, J. Chem. Soc. Perkin Trans. 2 1995, 1103; H. Ross, U. Lüning, Angew. Chem. 1995, 107, 2723; Angew. Chem. Int. Ed. Engl. 1995, 34, 2555.
11. Recent examples not included in ref. [1, 2]: O. Struck, L. A. J. Chrisstoffels, R. J. W. Lugtenberg, W. Verboom, G. J. van Hummel, S. Harkema, D. N. Reinhoudt, J. Org. Chem. 1997, 62, 2487; J. A. Perez-Adelmar, H. Abraham, C. Sanchez, K. Rissanen, P. Prados, J. de Mendoza, Angew. Chem. 1996, 108, 1088; Angew. Chem. Int. Ed. Engl. 1996, 55, 1009; M. A. McKervey, M. Pitarch, J. Chem. Soc. Chem. Commun, 1996, 1689; A. Siepen, A. Zett, F. Vögtle, Liebigs Ann. 1996, 757; P. Lhotak, S. Shinkai, Tetrahedron Lett. 1996, 37, 645; P. Lhotak, M. Kawaguchi, A. Ikeda, S. Shinkai. Tetrahedron 1996, 52, 12399; A. Arduini, S. Fanni, G. Manfredi, A. Pochini, R. Ungaro, A. R. Sicuri, F. Ugozzoli, J. Org. Chem. 1995, 60, 1448; F. Ohseto, S. Shinkai, J. Chem. Soc. Perkin Trans. 2 1995, 1103; H. Ross, U. Lüning, Angew. Chem. 1995, 107, 2723; Angew. Chem. Int. Ed. Engl. 1995, 34, 2555.
12. Recent examples not included in ref. [1, 2]: O. Struck, L. A. J. Chrisstoffels, R. J. W. Lugtenberg, W. Verboom, G. J. van Hummel, S. Harkema, D. N. Reinhoudt, J. Org. Chem. 1997, 62, 2487; J. A. Perez-Adelmar, H. Abraham, C. Sanchez, K. Rissanen, P. Prados, J. de Mendoza, Angew. Chem. 1996, 108, 1088; Angew. Chem. Int. Ed. Engl. 1996, 55, 1009; M. A. McKervey, M. Pitarch, J. Chem. Soc. Chem. Commun, 1996, 1689; A. Siepen, A. Zett, F. Vögtle, Liebigs Ann. 1996, 757; P. Lhotak, S. Shinkai, Tetrahedron Lett. 1996, 37, 645; P. Lhotak, M. Kawaguchi, A. Ikeda, S. Shinkai. Tetrahedron 1996, 52, 12399; A. Arduini, S. Fanni, G. Manfredi, A. Pochini, R. Ungaro, A. R. Sicuri, F. Ugozzoli, J. Org. Chem. 1995, 60, 1448; F. Ohseto, S. Shinkai, J. Chem. Soc. Perkin Trans. 2 1995, 1103; H. Ross, U. Lüning, Angew. Chem. 1995, 107, 2723; Angew. Chem. Int. Ed. Engl. 1995, 34, 2555.
13. Recent examples not included in ref. [1, 2]: O. Struck, L. A. J. Chrisstoffels, R. J. W. Lugtenberg, W. Verboom, G. J. van Hummel, S. Harkema, D. N. Reinhoudt, J. Org. Chem. 1997, 62, 2487; J. A. Perez-Adelmar, H. Abraham, C. Sanchez, K. Rissanen, P. Prados, J. de Mendoza, Angew. Chem. 1996, 108, 1088; Angew. Chem. Int. Ed. Engl. 1996, 55, 1009; M. A. McKervey, M. Pitarch, J. Chem. Soc. Chem. Commun, 1996, 1689; A. Siepen, A. Zett, F. Vögtle, Liebigs Ann. 1996, 757; P. Lhotak, S. Shinkai, Tetrahedron Lett. 1996, 37, 645; P. Lhotak, M. Kawaguchi, A. Ikeda, S. Shinkai. Tetrahedron 1996, 52, 12399; A. Arduini, S. Fanni, G. Manfredi, A. Pochini, R. Ungaro, A. R. Sicuri, F. Ugozzoli, J. Org. Chem. 1995, 60, 1448; F. Ohseto, S. Shinkai, J. Chem. Soc. Perkin Trans. 2 1995, 1103; H. Ross, U. Lüning, Angew. Chem. 1995, 107, 2723; Angew. Chem. Int. Ed. Engl. 1995, 34, 2555.
14. Recent examples not included in ref. [1, 2]: O. Struck, L. A. J. Chrisstoffels, R. J. W. Lugtenberg, W. Verboom, G. J. van Hummel, S. Harkema, D. N. Reinhoudt, J. Org. Chem. 1997, 62, 2487; J. A. Perez-Adelmar, H. Abraham, C. Sanchez, K. Rissanen, P. Prados, J. de Mendoza, Angew. Chem. 1996, 108, 1088; Angew. Chem. Int. Ed. Engl. 1996, 55, 1009; M. A. McKervey, M. Pitarch, J. Chem. Soc. Chem. Commun, 1996, 1689; A. Siepen, A. Zett, F. Vögtle, Liebigs Ann. 1996, 757; P. Lhotak, S. Shinkai, Tetrahedron Lett. 1996, 37, 645; P. Lhotak, M. Kawaguchi, A. Ikeda, S. Shinkai. Tetrahedron 1996, 52, 12399; A. Arduini, S. Fanni, G. Manfredi, A. Pochini, R. Ungaro, A. R. Sicuri, F. Ugozzoli, J. Org. Chem. 1995, 60, 1448; F. Ohseto, S. Shinkai, J. Chem. Soc. Perkin Trans. 2 1995, 1103; H. Ross, U. Lüning, Angew. Chem. 1995, 107, 2723; Angew. Chem. Int. Ed. Engl. 1995, 34, 2555.
15. Recent examples not included in ref. [1, 2]: O. Struck, L. A. J. Chrisstoffels, R. J. W. Lugtenberg, W. Verboom, G. J. van Hummel, S. Harkema, D. N. Reinhoudt, J. Org. Chem. 1997, 62, 2487; J. A. Perez-Adelmar, H. Abraham, C. Sanchez, K. Rissanen, P. Prados, J. de Mendoza, Angew. Chem. 1996, 108, 1088; Angew. Chem. Int. Ed. Engl. 1996, 55, 1009; M. A. McKervey, M. Pitarch, J. Chem. Soc. Chem. Commun, 1996, 1689; A. Siepen, A. Zett, F. Vögtle, Liebigs Ann. 1996, 757; P. Lhotak, S. Shinkai, Tetrahedron Lett. 1996, 37, 645; P. Lhotak, M. Kawaguchi, A. Ikeda, S. Shinkai. Tetrahedron 1996, 52, 12399; A. Arduini, S. Fanni, G. Manfredi, A. Pochini, R. Ungaro, A. R. Sicuri, F. Ugozzoli, J. Org. Chem. 1995, 60, 1448; F. Ohseto, S. Shinkai, J. Chem. Soc. Perkin Trans. 2 1995, 1103; H. Ross, U. Lüning, Angew. Chem. 1995, 107, 2723; Angew. Chem. Int. Ed. Engl. 1995, 34, 2555.
16. Recent examples not included in ref. [1, 2]: O. Struck, L. A. J. Chrisstoffels, R. J. W. Lugtenberg, W. Verboom, G. J. van Hummel, S. Harkema, D. N. Reinhoudt, J. Org. Chem. 1997, 62, 2487; J. A. Perez-Adelmar, H. Abraham, C. Sanchez, K. Rissanen, P. Prados, J. de Mendoza, Angew. Chem. 1996, 108, 1088; Angew. Chem. Int. Ed. Engl. 1996, 55, 1009; M. A. McKervey, M. Pitarch, J. Chem. Soc. Chem. Commun, 1996, 1689; A. Siepen, A. Zett, F. Vögtle, Liebigs Ann. 1996, 757; P. Lhotak, S. Shinkai, Tetrahedron Lett. 1996, 37, 645; P. Lhotak, M. Kawaguchi, A. Ikeda, S. Shinkai. Tetrahedron 1996, 52, 12399; A. Arduini, S. Fanni, G. Manfredi, A. Pochini, R. Ungaro, A. R. Sicuri, F. Ugozzoli, J. Org. Chem. 1995, 60, 1448; F. Ohseto, S. Shinkai, J. Chem. Soc. Perkin Trans. 2 1995, 1103; H. Ross, U. Lüning, Angew. Chem. 1995, 107, 2723; Angew. Chem. Int. Ed. Engl. 1995, 34, 2555.
17. Recent examples not included in ref. [1, 2]: O. Struck, L. A. J. Chrisstoffels, R. J. W. Lugtenberg, W. Verboom, G. J. van Hummel, S. Harkema, D. N. Reinhoudt, J. Org. Chem. 1997, 62, 2487; J. A. Perez-Adelmar, H. Abraham, C. Sanchez, K. Rissanen, P. Prados, J. de Mendoza, Angew. Chem. 1996, 108, 1088; Angew. Chem. Int. Ed. Engl. 1996, 55, 1009; M. A. McKervey, M. Pitarch, J. Chem. Soc. Chem. Commun, 1996, 1689; A. Siepen, A. Zett, F. Vögtle, Liebigs Ann. 1996, 757; P. Lhotak, S. Shinkai, Tetrahedron Lett. 1996, 37, 645; P. Lhotak, M. Kawaguchi, A. Ikeda, S. Shinkai. Tetrahedron 1996, 52, 12399; A. Arduini, S. Fanni, G. Manfredi, A. Pochini, R. Ungaro, A. R. Sicuri, F. Ugozzoli, J. Org. Chem. 1995, 60, 1448; F. Ohseto, S. Shinkai, J. Chem. Soc. Perkin Trans. 2 1995, 1103; H. Ross, U. Lüning, Angew. Chem. 1995, 107, 2723; Angew. Chem. Int. Ed. Engl. 1995, 34, 2555.
18. 2 group: K. Araki, K. Hisaichi, T. Kanai, S. Shinkai, Chem. Lett. 1995, 569.
19. The para positions (upper rim) of a calixarene system are commonly considered as the "head," while the OH groups (lower rim) represent the "tail": W. Wasikievicz, G. Rokicki, J. Kielkiewicz, V. Böhmer, Angew. Chem., 1994, 106, 230; Angew. Chem. Int. Ed. Engl. 1994, 33, 214.
20. The para positions (upper rim) of a calixarene system are commonly considered as the "head," while the OH groups (lower rim) represent the "tail": W. Wasikievicz, G. Rokicki, J. Kielkiewicz, V. Böhmer, Angew. Chem., 1994, 106, 230; Angew. Chem. Int. Ed. Engl. 1994, 33, 214.
21. The complete IUPAC name for this compound is 5,5′-bicalix[4]arene-25,25′,26,26′,27,27′,28,28′- octol.
22. a) C. D. Gutsche, L.-G. Lin, Tetrahedron 1986, 42, 1633;
23. b) C. D. Gutsche, L. J. Bauer, J. Am. Chem. Soc. 1985, 107, 6052.
24. R. Pummerer, E. Prell, A. Rieche, Ber. Dtsch. Chem. Ges. B 1926, 59, 2159.
25. -3; these residual electron densities could not be assigned to any chemically sensible moiety. Crystallographic data (excluding structure factors) for the structure reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC-100536. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK (fax: int. code + (44) 1223-336033; e-mail: deposit@chemcrys.cam.ac.uk).
26. A. Altomare, G. Cascarano, C. Giacovazzo, A. Guagliardi, M. C. Burla, G. Polidori, M. Camalli, J. Appl. Crystallogr. 1994, 27, 435.
27. M. Camalli, R. Spagna, J. Appl. Crystallogr. 1994, 27, 861.
28. E. G. Boonstra, Acta Crystallogr. 1963, 16, 816.
29. K. Iwamoto, K. Araki, S. Shinkai, J. Org. Chem. 1991, 56, 4955.
30. J.-D. van Loon, J. F. Heida, W. Verboom, D. N. Reinhoudt, Recl. Trav. Chim. Pays-Bas 1992, 111, 353.
31. 2bridged double calix[4]arene]
32. For the "up-down-up" stereochemical assignment of 7: C-M. Shu, W.-C Liu, M.-C. Ku, F.-S. Tang, M.-L. Veh, L.-G. Lin, J. Org. Chem. 1994, 59, 3730.
33. Further examples of biaryl coupling: M. Larsen, M. Jørgensen, J. Org. Chem. 1997, 62, 4171; S. Zhang, D. Zhang, L. S. Liebeskind, ibid. 1997, 62, 2312; N. G. Andersen, S. P. Maddaford, B. A. Keay, ibid. 1996, 61, 9556; N. Miyaura, A. Suzuki, Chem. Rev. 1995, 95, 2457; G. Sartori, R. Maggi, F. Bigi, M. Grandi, J. Org. Chem. 1994, 59, 3701; D. A. Whiting in Comprehensive Organic Synthesis, Vol. 3 (Eds.: B. M. Trost, I. Fleming), Pergamon, New York, 1991, p. 659; J. K. Stille, Angew. Chem. 1986, 98, 504; Angew. Chem. Int. Ed. Engl. 1986, 25, 508; E. Negishi, Acc. Chem. Res. 1982, 15, 340.
34. Further examples of biaryl coupling: M. Larsen, M. Jørgensen, J. Org. Chem. 1997, 62, 4171; S. Zhang, D. Zhang, L. S. Liebeskind, ibid. 1997, 62, 2312; N. G. Andersen, S. P. Maddaford, B. A. Keay, ibid. 1996, 61, 9556; N. Miyaura, A. Suzuki, Chem. Rev. 1995, 95, 2457; G. Sartori, R. Maggi, F. Bigi, M. Grandi, J. Org. Chem. 1994, 59, 3701; D. A. Whiting in Comprehensive Organic Synthesis, Vol. 3 (Eds.: B. M. Trost, I. Fleming), Pergamon, New York, 1991, p. 659; J. K. Stille, Angew. Chem. 1986, 98, 504; Angew. Chem. Int. Ed. Engl. 1986, 25, 508; E. Negishi, Acc. Chem. Res. 1982, 15, 340.
35. Further examples of biaryl coupling: M. Larsen, M. Jørgensen, J. Org. Chem. 1997, 62, 4171; S. Zhang, D. Zhang, L. S. Liebeskind, ibid. 1997, 62, 2312; N. G. Andersen, S. P. Maddaford, B. A. Keay, ibid. 1996, 61, 9556; N. Miyaura, A. Suzuki, Chem. Rev. 1995, 95, 2457; G. Sartori, R. Maggi, F. Bigi, M. Grandi, J. Org. Chem. 1994, 59, 3701; D. A. Whiting in Comprehensive Organic Synthesis, Vol. 3 (Eds.: B. M. Trost, I. Fleming), Pergamon, New York, 1991, p. 659; J. K. Stille, Angew. Chem. 1986, 98, 504; Angew. Chem. Int. Ed. Engl. 1986, 25, 508; E. Negishi, Acc. Chem. Res. 1982, 15, 340.
36. Further examples of biaryl coupling: M. Larsen, M. Jørgensen, J. Org. Chem. 1997, 62, 4171; S. Zhang, D. Zhang, L. S. Liebeskind, ibid. 1997, 62, 2312; N. G. Andersen, S. P. Maddaford, B. A. Keay, ibid. 1996, 61, 9556; N. Miyaura, A. Suzuki, Chem. Rev. 1995, 95, 2457; G. Sartori, R. Maggi, F. Bigi, M. Grandi, J. Org. Chem. 1994, 59, 3701; D. A. Whiting in Comprehensive Organic Synthesis, Vol. 3 (Eds.: B. M. Trost, I. Fleming), Pergamon, New York, 1991, p. 659; J. K. Stille, Angew. Chem. 1986, 98, 504; Angew. Chem. Int. Ed. Engl. 1986, 25, 508; E. Negishi, Acc. Chem. Res. 1982, 15, 340.
37. Further examples of biaryl coupling: M. Larsen, M. Jørgensen, J. Org. Chem. 1997, 62, 4171; S. Zhang, D. Zhang, L. S. Liebeskind, ibid. 1997, 62, 2312; N. G. Andersen, S. P. Maddaford, B. A. Keay, ibid. 1996, 61, 9556; N. Miyaura, A. Suzuki, Chem. Rev. 1995, 95, 2457; G. Sartori, R. Maggi, F. Bigi, M. Grandi, J. Org. Chem. 1994, 59, 3701; D. A. Whiting in Comprehensive Organic Synthesis, Vol. 3 (Eds.: B. M. Trost, I. Fleming), Pergamon, New York, 1991, p. 659; J. K. Stille, Angew. Chem. 1986, 98, 504; Angew. Chem. Int. Ed. Engl. 1986, 25, 508; E. Negishi, Acc. Chem. Res. 1982, 15, 340.
38. Further examples of biaryl coupling: M. Larsen, M. Jørgensen, J. Org. Chem. 1997, 62, 4171; S. Zhang, D. Zhang, L. S. Liebeskind, ibid. 1997, 62, 2312; N. G. Andersen, S. P. Maddaford, B. A. Keay, ibid. 1996, 61, 9556; N. Miyaura, A. Suzuki, Chem. Rev. 1995, 95, 2457; G. Sartori, R. Maggi, F. Bigi, M. Grandi, J. Org. Chem. 1994, 59, 3701; D. A. Whiting in Comprehensive Organic Synthesis, Vol. 3 (Eds.: B. M. Trost, I. Fleming), Pergamon, New York, 1991, p. 659; J. K. Stille, Angew. Chem. 1986, 98, 504; Angew. Chem. Int. Ed. Engl. 1986, 25, 508; E. Negishi, Acc. Chem. Res. 1982, 15, 340.
39. Further examples of biaryl coupling: M. Larsen, M. Jørgensen, J. Org. Chem. 1997, 62, 4171; S. Zhang, D. Zhang, L. S. Liebeskind, ibid. 1997, 62, 2312; N. G. Andersen, S. P. Maddaford, B. A. Keay, ibid. 1996, 61, 9556; N. Miyaura, A. Suzuki, Chem. Rev. 1995, 95, 2457; G. Sartori, R. Maggi, F. Bigi, M. Grandi, J. Org. Chem. 1994, 59, 3701; D. A. Whiting in Comprehensive Organic Synthesis, Vol. 3 (Eds.: B. M. Trost, I. Fleming), Pergamon, New York, 1991, p. 659; J. K. Stille, Angew. Chem. 1986, 98, 504; Angew. Chem. Int. Ed. Engl. 1986, 25, 508; E. Negishi, Acc. Chem. Res. 1982, 15, 340.
40. Further examples of biaryl coupling: M. Larsen, M. Jørgensen, J. Org. Chem. 1997, 62, 4171; S. Zhang, D. Zhang, L. S. Liebeskind, ibid. 1997, 62, 2312; N. G. Andersen, S. P. Maddaford, B. A. Keay, ibid. 1996, 61, 9556; N. Miyaura, A. Suzuki, Chem. Rev. 1995, 95, 2457; G. Sartori, R. Maggi, F. Bigi, M. Grandi, J. Org. Chem. 1994, 59, 3701; D. A. Whiting in Comprehensive Organic Synthesis, Vol. 3 (Eds.: B. M. Trost, I. Fleming), Pergamon, New York, 1991, p. 659; J. K. Stille, Angew. Chem. 1986, 98, 504; Angew. Chem. Int. Ed. Engl. 1986, 25, 508; E. Negishi, Acc. Chem. Res. 1982, 15, 340.
41. Further examples of biaryl coupling: M. Larsen, M. Jørgensen, J. Org. Chem. 1997, 62, 4171; S. Zhang, D. Zhang, L. S. Liebeskind, ibid. 1997, 62, 2312; N. G. Andersen, S. P. Maddaford, B. A. Keay, ibid. 1996, 61, 9556; N. Miyaura, A. Suzuki, Chem. Rev. 1995, 95, 2457; G. Sartori, R. Maggi, F. Bigi, M. Grandi, J. Org. Chem. 1994, 59, 3701; D. A. Whiting in Comprehensive Organic Synthesis, Vol. 3 (Eds.: B. M. Trost, I. Fleming), Pergamon, New York, 1991, p. 659; J. K. Stille, Angew. Chem. 1986, 98, 504; Angew. Chem. Int. Ed. Engl. 1986, 25, 508; E. Negishi, Acc. Chem. Res. 1982, 15, 340.