Novel and Efficient Cyanofluoromethylation Promoted by Samarium(II) Species

Yusuke Asano; Shoko Suzuki; Tadashi Aoyama; Kosuke Shimizu; Masatsugu Kajitani; Yasuo Yokoyama

doi:10.1055/s-2007-966006

Subscribe to RSS

Please copy the URL and add it into your RSS Feed Reader.

https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml

Share / Bookmark

Facebook X Linkedin Weibo

Download PDF

Synthesis 2007(9): 1309-1314
DOI: 10.1055/s-2007-966006

PAPER

Novel and Efficient Cyanofluoromethylation Promoted by Samarium(II) Species

Yusuke Asano^a, Shoko Suzuki^b, Tadashi Aoyama^c, Kosuke Shimizu^a, Masatsugu Kajitani^a, Yasuo Yokoyama*^a
^a Department of Chemistry, Faculty of Science and Technology, Sophia University, 7-1 Kioicho, Chiyoda-ku, Tokyo 102-8554, Japan
Fax: +81(3)32383361; e-Mail: yasuo-y@sophia.ac.jp;
^b National Institute of Advanced Industrial Science and Technology (AIST), Tsukuba, Ibaraki 305-8565, Japan
^c Department of Materials and Applied Chemistry, College of Science and Technology, Nihon University, 1-8-14 Kanda Surugadai, Chiyoda-ku, Tokyo 101-8308, Japan

Further Information

Publication History

Received 22 January 2007
Publication Date:
05 April 2007 (online)

Abstract
Full Text
References

Permissions and Reprints All articles of this category

Abstract

Two types of cyanofluoromethylation using a combination of samarium(II) species and chlorofluoroacetonitrile combination has been developed. One is a samarium(II) dibromide promoted reaction at low temperature, whereas the second synthetic method uses samarium(II) diiodide. These reactions proceeded smoothly to give the desired products in good to excellent yields.

Key words

cyanofluoromethylation - samarium(II) dibromide - samarium(II) diiodide - cyanohydrin - aldehyde

References

For selected papers and reviews, see:
1a Fukuzumi T. Shibata N. Sugiura M. Yasui H. Nakamura S. Toru T. Angew. Chem. Int. Ed. 2006, 45: 4973

Crossref Google Scholar
1b Iwai N. Kitazume T. Kagaku (Kyoto) 2004, 59: 74

Crossref Google Scholar
1c Tajima T. Fuchigami T. Yuki Denkai Gosei no Shintenkai 2004, 64

Crossref Google Scholar
1d Fustero S. Sanz-Cervera JF. Piera J. Sanchez-Rosello M. Chiva G. Simon-Fuentes A. J. Fluorine Chem. 2004, 125: 621

Crossref Google Scholar
1e Yoneda N. J. Fluorine Chem. 2004, 125: 7

Crossref Google Scholar
1f Ignat’ev N. Sartori P. J. Fluorine Chem. 2000, 101: 203

Crossref Google Scholar
1g Banks RE. Tatlow JC. Organofluorine Chem. 1994, 25

Crossref Google Scholar
1h Welch JT. Eshwarakrishman S. Fluorine in Bioorganic Chemistry Wiley; New York: 1991.

Crossref Google Scholar
1i Takeuchi Y. J. Synth. Org. Chem., Jpn. 1988, 46: 145

Crossref Google Scholar
1j Liebman JK. Greenberg A. Dolbier WR. Fluorine-containing Molecules, Structure, Reactivity, Synthesis VCH; New York: 1988.

Crossref Google Scholar
1k Filler R. Kobayashi Y. Biomedical Aspects of Fluorine Chemistry Kodansha Ltd.; Tokyo: 1982.

Crossref Google Scholar
1l Organofluorine Chemicals and Their Industrial Applications Banks RE. John Wiley & Sons; London: 1979.

Crossref Google Scholar
2 Peng W. Shreeve JM. Tetrahedron Lett. 2005, 46: 4905

Crossref Google Scholar
3 Laurent E. Marquet B. Tardivel R. Tetrahedron 1989, 45: 4431

Crossref Google Scholar
4a Venkatachalam TK. Uckun FM. Synth. Commun. 2004, 34: 2463

Google Scholar
4b Venkatachalam TK. Sudbeck EA. Mao C. Uckun FM. Antiviral Chem. Chemother. 2000, 11: 329

Google Scholar
5 Effenberger F. Osswald S. Tetrahedron: Asymmetry 2001, 12: 279

Crossref Google Scholar
Two examples of direct cyanofluoromethylation using fluoroacetonitrile-strong base combinations have already been reported.
6a With LDA as the strong base: van Steenis JH. van den Nieuwendijk AMCH. van der Gen A. J. Fluorine Chem. 2004, 125: 107

Google Scholar
6b With LiHMDS as the strong base: Patrick TB. Nadji S. J. Fluorine Chem. 1990, 49: 147

Google Scholar
7a Yokoyama Y. Ohira R. Tanaka H. Suzuki S. Kajitani M. Synth. Commun. 2004, 34: 2277

Crossref Google Scholar
7b Yokoyama Y. Mochida K. Synthesis 1999, 1319

Crossref Google Scholar
7c Yokoyama Y. Mochida K. Synthesis 1999, 676

Crossref Google Scholar
7d Yokoyama Y. Mochida K. Chem. Commun. 1998, 1093

Crossref Google Scholar
8a Dahlen A. Prasad E. Flowers RA. Hilmersson G. Chem. Eur. J. 2005, 11: 3279

Crossref Google Scholar
8b Kim M. Knettle BW. Dahlen A. Hilmersson G. Flowers RA. Tetrahedron 2003, 59: 10397

Crossref Google Scholar
8c Helion F. Lannou M.-I. Namy J.-L. Tetrahedron Lett. 2003, 44: 5507

Crossref Google Scholar
8d Knettle BW. Flowers RA. Org. Lett. 2001, 3: 2321

Crossref Google Scholar
8e Lebrun A. Rantze E. Namy J.-L. Kagan HB. New J. Chem. 1995, 19: 699

Crossref Google Scholar
8f Lebrun A. Namy J.-L. Kagan HB. Tetrahedron Lett. 1993, 34: 2311

Crossref Google Scholar
For selected reviews, see:
9a Edmonds DJ. Johnston D. Procter DJ. Chem. Rev. 2004, 104: 3371

Google Scholar
9b Berndt M. Gross S. Hoelemann A. Reissig H.-U. Synlett 2004, 422

Google Scholar
9c Kagan HB. Tetrahedron 2003, 59: 10351

Google Scholar
9d Matsuda F. Yuki Gosei Kagaku Kyokaishi 2001, 59: 92

Google Scholar
9e Utimoto K. Matsubara S. Yuki Gosei Kagaku Kyokaishi 1998, 56: 908

Google Scholar
9f Inanaga J. Trends Org. Chem. 1990, 1: 23

Google Scholar
10 Young JA. Tarrant P. J. Am. Chem. Soc. 1949, 71: 2432

Crossref Google Scholar