Highly chemoselective and enantiospecific Suzuki-Miyaura cross-couplings of benzylic organoboronic esters

Synthesis (Germany)

Volumn 45, Issue 13, 2013, Pages 1759-1763

  Glasspoole, Ben W ^a   Oderinde, Martins S ^a   Moore, Brandon D ^a   Antoft Finch, Aurora ^a   Crudden, Cathleen M ^a  

^a QUEEN S UNIVERSITY   (Canada)

Author keywords

chiral; cross coupling; enantiospecific; palladium; Suzuki

Indexed keywords

CHIRAL; CROSS-COUPLINGS; ENANTIOSPECIFIC; ENANTIOSPECIFICITY; MECHANISTIC STUDIES; SEQUENTIAL REACTION; SUZUKI; SUZUKI-MIYAURA CROSS-COUPLING REACTION;

ESTERS; PALLADIUM;

ESTERIFICATION;

1 (1 PHENYLETHYL)NAPHTHALENE; 1 PHENYL 1 (2 METHYLPHENYL)ETHANE; 1 PHENYL 1 (3,5 DIMETHYLPHENYL)ETHANE; 1 PHENYL 1 (4 ACETYLPHENYL)ETHANE; 1 PHENYL 1 (4 CHLOROPHENYL)ETHANE; 1 PHENYL 1 (4 METHOXYPHENYL)ETHANE; 1 PHENYL 1 (4 METHYLPHENYL)ETHANE; BENZYLIC BORONIC ESTER; CHEMICAL COMPOUND; ESTER DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHIRALITY; COMPLEX FORMATION; ELIMINATION REACTION; FLOW RATE; HECK REACTION; HYDROBORATION; MASS SPECTROMETRY; POROSITY; RACEMIZATION; STEREOCHEMISTRY; SUZUKI REACTION;

EID: 84879499332     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0033-1338875     Document Type: Article

References (28)

1. Wilczynski R., Sneddon L. G. J. Am. Chem. Soc.: 1980; 103 2857
2. Crudden C. M., Edwards D. Eur. J. Org. Chem.: 2003; 4695
3. Lata C. J., Crudden C. M. J. Am. Chem. Soc.: 2010; 132 131
4. Gonzalez A. Z., Roman J. G., Gonzalez E., Martinez J., Medina J. R., Matos K., Soderquist J. A. J. Am. Chem. Soc.: 2008; 130 9218
5. Smith S. M., Thacker N. C., Takacs J. M. J. Am. Chem. Soc.: 2008; 130 3734
6. Vogels C. M., Westcott S. A. Curr. Org. Chem.: 2005; 9 687
7. Carroll A. M., O'Sullivan T. P., Guiry P. J. Adv. Synth. Catal.: 2005; 347 609
8. Blume F., Zemolka S., Fey T., Kranich R., Schmalz H. G. Adv. Synth. Catal.: 2002; 344 868
9. Vogels C. M., Hayes P. G., Shaver M. P., Westcott S. A. Chem. Commun.: 2000; 51
10. Ramachandran P. V., Jennings M. P., Brown H. C. Org. Lett.: 1999; 1 1399
11. Beletskaya I., Pelter A. Tetrahedron: 1997; 53 4957
12. Brown J. M., Lloyd-Jones G. C. J. Am. Chem. Soc.: 1994; 116 866
13. Burgess K., Vanderdonk W. A., Westcott S. A., Marder T. B., Baker R. T., Calabrese J. C. J. Am. Chem. Soc.: 1992; 114 9350
14. Evans D. A., Fu G. C., Anderson B. A. J. Am. Chem. Soc.: 1992; 114 6679
15. Burgess K., Ohlmeyer M. J. Chem. Rev.: 1991; 91 1179
16. Hayashi T., Matsumoto Y., Ito Y. J. Am. Chem. Soc.: 1989; 111 3426
17. Mannig D., Noth H. Angew. Chem., Int. Ed. Engl.: 1985; 24 878
18. Fernandez E., Maeda K., Hooper M. W., Brown J. M. Chem. Eur. J.: 2000; 6 1840
19. Fernandez E., Hooper M. W., Knight F. I., Brown J. M. Chem. Commun.: 1997; 173
20. Rubina M., Rubin M., Gevorgyan V. J. Am. Chem. Soc.: 2003; 125 7198
21. Luithle J. E. A, Pietruszka J. J. Org. Chem.: 1999; 64 8287
22. Wang X.-Z, Deng M.-Z. J. Chem. Soc., Perkin Trans. 1: 1996; 2663
23. Dreher S. D., Dormer P. G., Sandrock D. L., Molander G. A. J. Am. Chem. Soc.: 2008; 130 9257
24. van den Hoogenband A., Lange J. H. M, Terpstra J. W., Koch M., Visser G. M., Visser M., Korstanje T. J., Jastrzebski J. T. B. H. Tetrahedron Lett.: 2008; 49 4122
25. Awano T., Ohmura T., Suginome M. J. Am. Chem. Soc.: 2011; 133 20738
26. Ohmura T., Awano T., Suginome M. J. Am. Chem. Soc.: 2010; 132 13191
27. Itami K., Tonogaki K., Ohashi Y., Yoshida J.-I. Org. Lett.: 2004; 6 4093
28. Itami K., Tonogaki K., Nokami T., Ohashi Y., Yoshida J.-I. Angew. Chem. Int. Ed.: 2006; 45 2404