Inter- and Intramolecular Additions of 1-Alkenylboronic Acids or Esters to Aldehydes and Ketones Catalyzed by Rhodium(I) Complexes in Basic, Aqueous Solutions

Akinori  Takezawa; Kenji  Yamaguchi; Toshimichi  Ohmura; Yasunori  Yamamoto; Norio  Miyaura

doi:10.1055/s-2002-34219

LETTER

Inter- and Intramolecular Additions of 1-Alkenylboronic Acids or Esters to Aldehydes and Ketones Catalyzed by Rhodium(I) Complexes in Basic, Aqueous Solutions

Akinori Takezawa, Kenji Yamaguchi, Toshimichi Ohmura, Yasunori Yamamoto, Norio Miyaura*
Division of Molecular Chemistry, Graduate School of Engineering, Hokkaido University, Sapporo 060-8628, Japan
Fax: +81(11)7066561; e-Mail: miyaura@org-mc.eng.hokudai.ac.jp;

Abstract

All articles of this category

Abstract

Grignard-type addition reaction of 1-alkenylboronic acids or their esters to aldehydes or ketones were carried out in aqueous MeOH or DME in the presence of KOH (1 equivalent) and an RhCl(dppf) or Rh(OH)(dppf) catalyst (3 mol%). The utility of the protocol was demonstrated in the corresponding intramolecular reaction giving cyclic homoallylic alcohols.

Key words

alkenylboron - rhodium catalyst - addition

Full Text

References

1a Oi S. Moro M. Inoue Y. Chem. Commun. 1997, 1621

1b Oi S. Moro M. Ono S. Inoue Y. Chem. Lett. 1998, 83

1c Hayashi T. Ishigedani M. J. Am. Chem. Soc. 2000, 122: 976

2a Oi S. Moro M. Inoue Y. Organometallics 2001, 20: 1036

2b Fujii T. Koike T. Mori A. Osakada K. Synlett 2002, 298

3 Ichiyanagi T. Kuniyama S. Simizu M. Fujisawa T. Chem. Lett. 1998, 1033

4a Nakamura H. Iwama H. Yamamoto Y. J. Am. Chem. Soc. 1996, 118: 6641

4b Nakamura H. Nakamura K. Yamamoto Y. J. Am. Chem. Soc. 1998, 120: 4242

5 Nakamura K. Nakamura H. Yamamoto Y. J. Org. Chem. 1999, 64: 2614

6a Sakai M. Ueda M. Miyaura N. Angew. Chem. Int. Ed. 1998, 37: 3279

6b Ueda M. Miyaura N. J. Org. Chem. 2000, 65: 4450

6c Ueda M. Saito A. Miyaura N. Synlett 2000, 1637

7 Fürstner A. Krause H. Adv. Synth. Catal. 2001, 343

8 Batey RA. Thadani AN. Smil DV. Org. Lett. 1999, 1: 1683

9 Krug C. Hartwig JF. J. Am. Chem. Soc. 2002, 124: 1674

10a Sakai M. Hayashi H. Miyaura N. Organometallics 1997, 16: 4229

10b Takaya Y. Ogasawara M. Hayashi T. Sakai M. Miyaura N. J. Am. Chem. Soc. 1998, 120: 5579

10c Sakuma S. Sakai M. Miyaura N. J. Org. Chem. 2000, 65: 5951

10d Itooka R. Iguchi Y. Miyaura N. Chem. Lett. 2001, 722

10e Sakuma S. Miyaura N. J. Org. Chem. 2001, 66: 8944

11 Grushin VV. Kuznetsov VF. Bensimon C. Alper H. Organometallics 1995, 14: 3927

12 Ohmura T. Yamamoto Y. Miyaura N. J. Am. Chem. Soc. 2000, 122: 4990