Preparation and selective reactions of mixed bimetallic aromatic and heteroaromatic boron-magnesium reagents

Angewandte Chemie - International Edition

Volumn 44, Issue 20, 2005, Pages 3133-3135

  Baron, Oliver ^a   Knochel, Paul ^a  

^a UNIVERSITY OF MUNICH   (Germany)

Author keywords

Boronic esters; Cross coupling; Heterocycles; Magnesium; Palladium

Indexed keywords

BORON; ESTERS; MAGNESIUM PRINTING PLATES; MAGNETIZATION;

BIMETALLIC COMPOUNDS; BORONIC ESTERS; HETEROAROMATIC COMPOUNDS; SUZUKI CROSS-COUPLING REACTIONS;

REACTION KINETICS;

BENZENE DERIVATIVE; BIPHENYL DERIVATIVE; BORONIC ACID DERIVATIVE; COPPER; ESTER; INDOLE DERIVATIVE; LITHIUM; MAGNESIUM; PALLADIUM; PYRIDINE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; SYNTHESIS;

BENZENE DERIVATIVES; BIPHENYL COMPOUNDS; BORONIC ACIDS; COPPER; ESTERS; INDOLES; LITHIUM; MAGNESIUM; MOLECULAR STRUCTURE; PALLADIUM; PYRIDINES;

EID: 18844440955     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200462928     Document Type: Article

References (25)

1. For recent advances in the selective functionalization of aromatic systems, see: a) J. Clayden, Organolithiums: Selectivity for Synthesis, Pergamon, New York, 2002;
2. b) M. C. Whisler, S. MacNeil, V. Snieckus, P. Beak, Angew. Chem. 2004, 116, 2256;
3. Angew. Chem. Int. Ed. 2004, 43, 2206;
4. c) R. R. Milburn, V. Snieckus, Angew. Chem. 2004, 116, 906;
5. Angew. Chem. Int. Ed. 2004, 43, 888;
6. d) M. G. Debije, J. Piris, M. P. De Haas, J. M. Warman, Z. Tomovic, C. D. Simpson, M. D. Watson, K. Müllen, J. Am. Chem. Soc. 2004, 126, 4641;
7. e) J. Qu, C. Kohl, M. Pottek, K. Müllen, Angew. Chem. 2004, 116, 1554;
8. Angew. Chem. Int. Ed. 2004, 43, 1528;
9. f) J. T. Suri, D. B. Cordes, F. E. Cappuccio, R. A. Wessling, B. Singaram, Angew. Chem. 2003, 115, 6037;
10. Angew. Chem. Int. Ed. 2003, 42, 5857.
11. a) I. Marek, Chem. Rev. 2000, 100, 2887;
12. b) I. Marek, Tetrahedron 2002, 58, 9463.
13. The iodoaryl boronic esters 4a-c were prepared by the treatment of the corresponding iodoaryl magnesium chlorides, obtained in turn by I/Mg exchange, with 10 (THF, -78→25°C, 1-3 h, 86-91 %); see Supporting Information. a) A. Finch, P. J. Gardner, E. J. Pearn, Recl. Trav. Chim. Pays-Bas 1964, 83, 1314;
14. b) R. W. Hoffmann, A. Endesfelder, H.-J. Zeiss, Carbohydr. Res. 1983, 123, 320.
15. a) A. Krasovskiy, P. Knochel, Angew. Chem. 2004, 116, 3396;
16. Angew. Chem. Int. Ed. 2004, 43, 3333;
17. b) F. Kopp, A. Krasovskiy, P. Knochel, Chem. Commun. 2004, 2288;
18. c) H. Ren, A. Krasovskiy, P. Knochel, Org. Lett. 2004, 6, 4215.
19. P. Knochel, M. C. P. Yeh, S. C. Berk, J. Talbert, J. Org. Chem. 1988, 53, 2390.
20. M. Winkler, B. Cakir, W. Sander, J. Am. Chem. Soc. 2004, 126, 6135.
21. a) B. Witulski, N. Buschmann, U. Bergsträßer, Tetrahedron 2000, 56, 8473;
22. b) M. G. Saulnier, G. W. Gribble, J. Org. Chem. 1982, 47, 757.
23. A. Staubitz, W. Dohle, P. Knochel, Synthesis 2003, 233.
24. a) N. Miyaura, A. Suzuki, Chem. Rev. 1995, 95, 2457;
25. b) G. A. Molander, B. Biolatto, J. Org. Chem. 2003, 68, 4302.