Palladium-catalyzed cross-coupling reaction of cyclopropylboronic acids with aryl triflates

Synthesis

Volumn , Issue 8, 2000, Pages 1095-1100

  Yao, Min Liang ^a   Deng, Min Zhi ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

Aryl triflates; Cyclopropylboronic acids; Optically active cyclopropylboronic acids; Suzuki coupling reaction; Trans cyclopropylarenes

Indexed keywords

BORONIC ACID DERIVATIVE; CYCLOPROPANE DERIVATIVE; PALLADIUM; TRIFLUOROMETHANESULFONIC ACID;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; ELECTRON TRANSPORT; OPTICAL ROTATION; REACTION ANALYSIS;

EID: 0033941845     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2000-6313     Document Type: Article

References (24)

1. Levy, B. D.; Petasis, N. A.; Scrhan, C. N. Nature 1997, 389, 985. Mohapatra, D. K.; Datta, A. J. Org. Chem. 1998, 63, 642; and references cited therein. Connor, D. T.; Strindtmann, M. J. Org. Chem. 1978, 43, 4603.
2. Levy, B. D.; Petasis, N. A.; Scrhan, C. N. Nature 1997, 389, 985. Mohapatra, D. K.; Datta, A. J. Org. Chem. 1998, 63, 642; and references cited therein. Connor, D. T.; Strindtmann, M. J. Org. Chem. 1978, 43, 4603.
3. Levy, B. D.; Petasis, N. A.; Scrhan, C. N. Nature 1997, 389, 985. Mohapatra, D. K.; Datta, A. J. Org. Chem. 1998, 63, 642; and references cited therein. Connor, D. T.; Strindtmann, M. J. Org. Chem. 1978, 43, 4603.
4. Wong, H. N. C.; Hon, M. -Y.; Tse, C. -W.; Yip, Y. -C.; Tanko, J.; Hudlicky, T. Chem. Rev. 1989, 89, 165. Feldman, K.; Berven, H. M.; Winreb, P. N. J. Am. Chem. Soc. 1993, 115, 11364.
5. Wong, H. N. C.; Hon, M. -Y.; Tse, C. -W.; Yip, Y. -C.; Tanko, J.; Hudlicky, T. Chem. Rev. 1989, 89, 165. Feldman, K.; Berven, H. M.; Winreb, P. N. J. Am. Chem. Soc. 1993, 115, 11364.
6. Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457. Suzuki, A. J. Organomet. Chem. 1999, 576, 147.
7. Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457. Suzuki, A. J. Organomet. Chem. 1999, 576, 147.
8. Charette, A. B.; Giroux, A. J. Org. Chem. 1996, 67, 8718.
9. Hildebrand, J. P.; Marsden, S. P. Synlett 1996, 893.
10. Wang, X. -Z.; Deng, M. -Z. J. Chem. Soc., Perkin. Trans 1, 1996, 2663.
11. Scott, W. J.; Stille, J. K. J. Am. Chem. Soc. 1986, 108, 3033. Saulnier, M. G.; Kadow, J. F.; Tun, M. M.; Langley, D. R.; Vyas, D. M. J. Am. Chem. Soc. 1989, 8320.
12. Scott, W. J.; Stille, J. K. J. Am. Chem. Soc. 1986, 108, 3033. Saulnier, M. G.; Kadow, J. F.; Tun, M. M.; Langley, D. R.; Vyas, D. M. J. Am. Chem. Soc. 1989, 8320.
13. Stang, P. J.; Hanack, M.; Subramanian, L. R. Synthesis 1982, 85. Ritter, K. Synthesis 1993, 735.
14. Stang, P. J.; Hanack, M.; Subramanian, L. R. Synthesis 1982, 85. Ritter, K. Synthesis 1993, 735.
15. (a) Ohe, T.; Miyaura, N.; Suzuki, A. Synlett 1990, 221.
16. (b) Ohe, T.; Miyaura, N.; Suzuki, A. J. Org. Chem. 1993, 58, 2201.
17. Mu, Y. -Q.; Gibbs, R. S. Tetrahedron Lett. 1995, 36, 5669.
18. Wiberg, K. B. Acc. Chem. Res. 1996, 29, 229.
19. Echavarren, A. M.; Stille, J. K. J. Am. Chem. Soc. 1987, 109, 5478.
20. Kong, K. -C.; Cheng, C. -H. J. Am. Chem. Soc. 1991, 113, 6313. O'Keef, D. F.; Dannock, M. C.; Marcuceio, S. M. Tetrahedron Lett. 1992, 33, 6679.
21. Kong, K. -C.; Cheng, C. -H. J. Am. Chem. Soc. 1991, 113, 6313. O'Keef, D. F.; Dannock, M. C.; Marcuceio, S. M. Tetrahedron Lett. 1992, 33, 6679.
22. c. All these facts suggested that 3j is pure trans-2-butylcyclopropylarene.
23. Zhou, S. -M.; Deng, M. -Z. Xia, L. -J.; Tang, M. -H. Angew. Chem., Int. Ed. 1998, 37, 2845. (formula presented)
24. Mintas, M.; Mannschreck, A. J. Chem. Soc., Chem. Commun. 1979, 602.