Samarium-Promoted Michael Addition
between Aroyl Chlorides and Chalcones

Yongjun Liu; Yuanying Li; Yan Qi; Jun Wan

doi:10.1055/s-0030-1258287

PAPER

Samarium-Promoted Michael Addition between Aroyl Chlorides and Chalcones

Yongjun Liu, Yuanying Li, Yan Qi, Jun Wan*
State Key Laboratory Base of Eco-chemical Engineering, College of Chemistry and Molecular Engineering, Qingdao University of Science and Technology, Qingdao 266042, P. R. of China
Fax: +86(532)84023927; e-Mail: wanjundz@sohu.com;

Abstract

All articles of this category

Abstract

A novel Michael addition type reaction between aroyl chlorides and chalcones was realized in the presence of samarium metal when N,N-dimethylformamide was used as a solvent. A variety of 1,4-diketones were thereby synthesized in moderate to good yields. The possible mechanism is also discussed.

Key words

samarium - Michael addition - aroyl chlorides - chalcones - 1,4-diketones

Full Text

References

For recent reports on the application of the Michael addition in organic synthesis, see:

1a Xia X.-F. Shu X.-Z. Ji K.-G. Yang Y.-F. Shaukat A. Liu X.-Y. Liang Y.-M. J. Org. Chem. 2010, 75: 2893

1b Attanasi OA. Favi G. Filippone P. Mantellini F. Moscatelli G. Perrulli FR. Org. Lett. 2010, 12: 468

1c Luna LE. Seoane G. Cravero RM. Eur. J. Org. Chem. 2008, 1271

1d Kazmaier U. Angew. Chem. Int. Ed. 2009, 48: 5790

2a Bower J. Box MR. Czyzewski M. Goeta AE. Steel PG. Org. Lett. 2009, 11: 2744

2b Mattson AE. Bharadwaj AR. Scheidt KA. J. Am. Chem. Soc. 2004, 126: 2314

2c Mattson AE. Bharadwaj AR. Zuhl AM. Scheidt KA. J. Org. Chem. 2006, 71: 5715

2d Han Z. Fujioka T. Usugi S.-i. Yorimitsu H. Shinokubo H. Oshima K. Org. Biomol. Chem. 2005, 3: 1622

2e Ohno T. Sakai M. Ishino Y. Shibata T. Maekawa H. Nishiguchi I. Org. Lett. 2001, 3: 3439

For examples, see:

3a Menard F. Weise CF. Lautens M. Org. Lett. 2007, 9: 5365

3b Demir AS. Reis Ö. Igdir AÇ. Esiringü I. Eymur S. J. Org. Chem. 2005, 70: 10584

3c Hashimoto T. Hirose M. Maruoka K. J. Am. Chem. Soc. 2008, 130: 7556

4a Sun F.-G. Huang X.-L. Ye S. J. Org. Chem. 2010, 75: 273

4b Sánchez-Larios E. Gravel M. J. Org. Chem. 2009, 74: 7536

4c DiRocco DA. Oberg KM. Dalton DM. Rovis T. J. Am. Chem. Soc. 2009, 131: 10872

4d Liu Q. Rovis T. Org. Lett. 2009, 11: 2856

4e Christmann M. Angew. Chem. Int. Ed. 2005, 44: 2632

5 Hassner A. In Comprehensive Organic Synthesis Vol. 1: Trost BM. Pergamon Press; Oxford: 1991. p.541-577

6a Nicolaou KC. Ellery SP. Chen JS. Angew. Chem. Int. Ed. 2009, 48: 7140

6b Procter DJ. Flowers RA. Skrydstrup T. Organic Synthesis Using Samarium Diiodide: A Practical Guide Royal Society of Chemistry Publishing; Cambridge: 2009.

6c Flowers RA. Synlett 2008, 1427

6d Edmonds DJ. Johnston D. Procter DJ. Chem. Rev. 2004, 104: 3371

7 For a review of the use of metallic samarium, see: Banik BK. Eur. J. Org. Chem. 2002, 2431

8a Ghatak A. Becker FF. Banik BK. Tetrahedron Lett. 2000, 41: 3793

8b Talukdar S. Fang J.-M. J. Org. Chem. 2001, 66: 330

For example, see:

9a Liu Y. Zhang F. Qi Y. Zhang Y. Zhang S. Eur. J. Org. Chem. 2008, 5470

9b Liu Y. Xu X. Zhang Y. Synlett 2004, 445

9c Liu Y. Zhang Y. Tetrahedron Lett. 2004, 45: 1295

9d Liu Y. Zhang Y. Tetrahedron 2003, 59: 8429

10a Liu Y. Wang X. Zhang Y. Synth. Commun. 2004, 34: 4009

10b Liu Y. Dai N. Qi Y. Zhang S. Synth. Commun. 2009, 39: 799

11a Ujikawa O. Inanaga J. Yamaguchi M. Tetrahedron Lett. 1989, 30: 2837

11b Inanaga J. Katsuki J. Ujikawa O. Yamaguchi M. Tetrahedron Lett. 1991, 32: 4921

For example, see:

12a Wilson DC. Liu S. Chen X. Meyers EA. Bao X. Prosvirin AV. Dunbar KR. Hadad CM. Shore SG. Inorg. Chem. 2009, 48: 5725

12b Ishiguro S. Takahashi R. Ozutsumi K. Kidorui 1994, 24: 96 ; Chem. Abstr. 1994, 121, 118731j

12c Hanawa H. Kii S. Asao N. Maruoka K. Tetrahedron Lett. 2000, 41: 5543