Nickel-catalyzed cross-coupling reaction of alkenyl methyl ethers with aryl boronic esters

Organic Letters

Volumn 11, Issue 21, 2009, Pages 4890-4892

  Shimasaki, Toshiaki ^a   Konno, Yuko ^a   Tobisu, Mamoru ^a   Chatani, Naoto ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 70350634100     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol901978e     Document Type: Article

References (33)

1. For general reviews of metal-catalyzed cross-coupling reactions, see: (a) Metal-Catalyzed Cross-Coupling Reactions; de Meijere, A., Diederich, F., Eds.; Wiley-VCH: New York, 2004.
2. (b) Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E.-i., Ed.; Wiley-Interscience: New York, 2002.
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5. (c) Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457.
6. Other minor electrophiles applicable to Suzuki-Miyaura reaction: Diazonium salts: (a) Roglans, A.; Pla-Quintana, A.; Moreno-Mañas, M. Chem. Rev. 2006, 106, 4622. Phosphonium salts:
7. (b) Hwang, L. K.; Na, Y.; Lee, J.; Do, Y.; Chang, S. Angew. Chem., Int. Ed. 2005, 44, 6166. Ammonium salts:
8. (c) Blakey, S. B.; MacMillan, D. W. C. J. Am. Chem. Soc. 2003, 125, 6046. Sulfonium salts:
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10. 3:
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17. (b) Kakiuchi, F.; Usui, M.; Ueno, S.; Chatani, N.; Murai, S. J. Am. Chem. Soc. 2004, 126, 2706.
18. Cross-coupling reactions of aryl methyl ethers with Grignard reagents: (a) Wenkert, E.; Michelotti, E. L.; Swindell, C. S. J. Am. Chem. Soc. 1979, 101, 2246.
19. (b) Wenkert, E.; Michelotti, E. L.; Swindell, C. S.; Tingoli, M. J. Org. Chem. 1984, 49, 4894.
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23. Catalytic amination of aryl methyl ethers: Tobisu, M.; Shimasaki, T.; Chatani, N. Chem. Lett. 2009, 38, 710.
24. (a) Guan, B.-T.; Wang, Y.; Li, B.-J.; Yu, D.-G.; Shi, Z.-J. J. Am. Chem. Soc. 2008, 130, 14468.
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27. If the reaction proceeds through the addition of arylnickelate complex followed by β-OMe elimination, inversion of the stereochemistry would be expected.
28. The alkenyl methyl ether can be readily prepared either by Wittig reaction of the corresponding carbonyl compounds or by the acid-mediated elimiation of MeOH of the corresponding dimethy acetáis. See the Supporting Information for details.
29. For recent examples, see: (a) Kim, S.-K.; Park, Y.-I.; Kang, I.-N.; Park, J.-W. J. Mater. Chem. 2007, 17, 4670.
30. (b) Ogata, A.; Anno, S.; Kuráta, T.; Xu, S.; Tsubouchi, A.; Takeda, T. Synlett 2007, 11, 1715.
31. (a) Tobisu, M.; Chatani, N. Angew Chem., Int. Ed. 2009, 48, 3565.
32. (b) Wang, C.; Glorius, F. Angew. Chem., Int. Ed. 2009, 48, 5240.
33. Quite recently, Rh-catalyzed coupling reaction of vinyl acetates with boronic esters was reported: Yu, J.-Y.; Kuwano, R. Angew. Chem., Int. Ed. 2009, 48, 7217.