Regioselective rhodium-catalyzed addition of arylboronic acids to alkynes with a pyridine-substituted water-soluble ligand

Organic Letters

Volumn 4, Issue 1, 2002, Pages 123-125

  Lautens, Mark ^a   Yoshida, Masahiro ^a  

^a UNIVERSITY OF TORONTO   (Canada)

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ARTICLE;

EID: 0000604304     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol010261t     Document Type: Article

References (26)

1. For reviews of organic synthesis in water, see: (a) Organic Synthesis in Water; Grieco, P. A., Ed.; Blacky Academic and Professional: London, 1998.
2. (b) Li, C. J.; Chan, T. H. Organic Reactions in Organic Media; John Wiley and Sons: New York, 1997.
3. (c) Cornils, B.; Herrmann, W. A. Aqueous Phase Organoinetallic Chemistry: Concepts and Applications; Wiley-VCH: Weinheim, 1998.
4. (d) Li, C. J. Chem. Rev. 1993, 93, 2023.
5. (e) Li, C. J.; Chan, T. H. Tetrahedron 1999, 55, 11149.
6. (f) Li, C. J. Tetrahedron 1996, 52, 5643.
7. Other examples of the rhodium-catalyzed additions of arylboronic acids to olefins. For additions to enones, see: (a) Sakai, M.; Hayashi, M.; Miyaura, N. Organometallics 1997, 16, 4229.
8. (b) Takaya, Y.; Ogasawara, M.; Hayashi, T.; Sakai, M.; Miyaura, N. J. Am. Chem. Soc. 1998, 120, 5579.
9. For additions to α,β-unsaturated esters, see: (c) Sakuma, S.; Sakai, M.; Itooka, R.; Miyaura, N. J. Org. Chem. 2000, 65, 5951.
10. For additions to vinyl phosphonates, see: (d) Hayashi, T.; Senda, T.; Takaya, Y.; Ogasawara, M. J. Am. Chem. Soc. 1999, 121, 11591.
11. For additions to vinyl nitro compounds, see: (e) Hayashi, T.; Senda, T.; Ogasawara, M. J. Am. Chem. Soc. 2000, 122, 10716.
12. Lautens, M.; Roy, A.; Fukuoka, K.; Fagnou, K.; Martín-Matute, B. J. Am. Chem. Soc. 2001, 123, 5358.
13. Synthesis of ligand 3: Herd, O.; Langhans, P. K.; Stelzer, O. Angew. Chem., Int. Ed. Engl. 1993, 32, 1058.
14. These ligands are available commercially from Strem Chemicals.
15. Additives such as pyridine were found to influence the ratio of Heck-type products to addition products in some substrates. A detailed description of these results will appear in the full paper on this reaction.
16. Hayashi, T.; Inoue, K.; Taniguchi, N.; Ogasawara, M. J. Am. Chem. Soc. 2001, 123, 9918.
17. (a) Brune, H.-A.; Unsin, J.; Hemmer, R.; Reichhardt, M. J. Organomet. Chem. 1989, 369, 335.
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21. (b) Jun, C.-H.; Lee, H.; Moon, C. H.; Hong, H.-S. J. Am. Chem. Soc. 2001, 123, 8600.
22. (c) Jun, C.-H.; Lee, H.; Lim, S.-G. J. Am. Chem. Soc. 2001, 123, 751.
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24. (e) Jun, C.-H.; Lee, H. J. Am. Chem. Soc. 1999, 121, 880.
25. (f) Jun, C.-H.; Lee, D.-Y.; Hong, J.-B. Tetrahedron Lett. 1997, 38, 6673.
26. (g) Jun, C.-H.; Lee, H.; Hong, J.-B. J. Org. Chem. 1997, 62, 1200.