Heck Vinylations Using Vinyl Sulfide, Vinyl Sulfoxide, Vinyl Sulfone, or Vinyl Sulfonate Derivatives and Aryl Bromides Catalyzed by a Palladium Complex Derived from a Tetraphosphine

Ahmed Battace; Touriya Zair; Henri Doucet; Maurice Santelli

doi:10.1055/s-2006-950244

PAPER

Heck Vinylations Using Vinyl Sulfide, Vinyl Sulfoxide, Vinyl Sulfone, or Vinyl Sulfonate Derivatives and Aryl Bromides Catalyzed by a Palladium Complex Derived from a Tetraphosphine

Ahmed Battace^a, Touriya Zair^b, Henri Doucet*^a, Maurice Santelli*^a
^a UMR 6180 CNRS and Université d"Aix-Marseille III: ‘Chirotechnologies : catalyse et biocatalyse’, Laboratoire de Synthèse Organique, Faculté des Sciences de Saint Jérôme, Université d"Aix-Marseille III, Avenue Escadrille Normandie-Niemen, 13397 Marseille Cedex 20, France
Fax: +33(4)91983865; e-Mail: henri.doucet@univ-cezanne.fr; e-Mail: m.santelli@univ-cezanne.fr;
^b Laboratoire de Chimie Organique Appliquée, Faculté des Sciences, Université Moulay Ismail, BP 4010, Beni M’mhammed, 50000 Meknes, Morocco

Abstract

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Abstract

The adverse impact of sulfur compounds on catalytic performance is well known. The tetraphosphine cis,cis,cis-1,2,3,4-tetrakis[(diphenylphosphino)methyl]cyclopentane in combination with allylchloropalladium dimer affords an efficient catalyst for the Heck reaction of sulfur-containing alkenes with aryl bromides. The rates and yields of the reactions strongly depend on the oxidation state of the sulfur atom. Using vinyl sulfides with 1 mol% catalyst, low to moderate yields of arylated alkenes were obtained. Phenyl vinyl sulfoxide was found to be more reactive, and satisfactory yields of (E)-[2-(phenylsulfinyl)vinyl]benzene derivatives were obtained using 1 mol% catalyst. With methyl vinyl sulfone, very high yields of (E)-[2-(methylsulfonyl)vinyl]benzene derivatives were obtained using 1-0.1 mol% catalyst. Phenyl vinyl sulfone and phenyl vinylsulfonate also gave high yields of the expected products, but in the presence of 0.4-1 mol% catalyst.

Key words

Heck reaction - palladium - phosphine - vinylsulfur - catalyst

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References

1 Beletskaya I. Cheprakov A. Chem. Rev. 2000, 100: 3009

2 Withcombe N. Hii (Mimi) KK. Gibson S. Tetrahedron 2001, 57: 7449

3 Littke A. Fu G. Angew. Chem. Int. Ed. 2002, 41: 4176

4 Farina V. Adv. Synth. Catal. 2004, 346: 1553

5 Trost BM. Tanigawa Y. J. Am. Chem. Soc. 1979, 101: 4743

6a Itami K. Mineno M. Muraoka N. Yoshida J.-I. J. Am. Chem. Soc. 2004, 126: 11778

6b Itami K. Higashi S. Mineno M. Yoshida J.-I. Org. Lett. 2005, 7: 1219

7a Somei M. Yamada F. Ohnishi H. Heterocycles 1987, 11: 2823

7b Wada A. Ohki K. Nagai S. Kanatomo S. J. Heterocycl. Chem. 1991, 28: 509

7c Buezo ND. Alonso I. Carretero JC. J. Am. Chem. Soc. 1998, 120: 7126

7d Priego J. Carretero JC. Synlett 1999, 1603

7e Alonso I. Carretero JC. J. Org. Chem. 2001, 66: 4453

8a Hirooka S. Tanbo Y. Takemura K. Nakahashi H. Matsuoka T. Kuroda S. Bull. Chem. Soc. Jpn. 1991, 64: 1431

8b Harada H. Kazami J.-I. Watanuki S. Tsuzuki R. Sudoh K. Fujimori A. Sanagi M. Orita M. Nakahara H. Shimaya J. Tsukamoto S.-I. Tanaka A. Yanagisawa I. Bioorg. Med. Chem. 2001, 9: 2955

8c Harada H. Kazami J.-I. Watanuki S. Tsuzuki R. Sudoh K. Fujimori A. Tokunaga T. Tanaka A. Tsukamoto S.-I. Yanagisawa I. Chem. Pharm. Bull. 2001, 49: 1593

8d Hirayama F. Koshio H. Ishihara T. Watanuki S. Hachiya S. Kaizawa H. Kuramochi T. Katayama N. Kurihara H. Taniuchi Y. Sato K. Sakai-Moritani Y. Kaku S. Kawasaki T. Matsumoto Y. Sakamoto S. Tsukamoto S.-I. Bioorg. Med. Chem. 2002, 10: 2597

9a Dickinson RP. Dack KN. Long CJ. Steele J. J. Med. Chem. 1997, 40: 3442

9b Orita A. Katakami M. Yasui Y. Kurihara A. Otera J. Green Chem. 2001, 3: 13

10 Berteina S. Wendeborn S. Brill WK.-D. De Mesmaeker A. Synlett 1998, 676

11 Uozumi Y. Kimura T. Synlett 2002, 2045

12 Zeng B.-B. King SB. Synthesis 2002, 2335

13 Laurenti D. Feuerstein M. Pèpe G. Doucet H. Santelli M. J. Org. Chem. 2001, 66: 1633

14 Feuerstein M. Laurenti D. Bougeant C. Doucet H. Santelli M. Chem. Commun. 2001, 325

15 Feuerstein M. Berthiol F. Doucet H. Santelli M. Org. Biomol. Chem. 2003, 1: 2235

16 Feuerstein M. Doucet H. Santelli M. J. Org. Chem. 2001, 66: 5923

17a Feuerstein M. Doucet H. Santelli M. Synlett 2001, 1980

17b Feuerstein M. Doucet H. Santelli M. Tetrahedron Lett. 2002, 43: 2191

17c Berthiol F. Doucet H. Santelli M. Tetrahedron Lett. 2003, 44: 1221

17d Lemhadri M. Doucet H. Santelli M. Tetrahedron 2004, 60: 11533

17e Berthiol F. Doucet H. Santelli M. Tetrahedron Lett. 2004, 45: 5633

17f Berthiol F. Doucet H. Santelli M. Eur. J. Org. Chem. 2005, 1367

17g Berthiol F. Doucet H. Santelli M. Synthesis 2005, 3589

17h Battace A. Zair T. Doucet H. Santelli M. J. Organomet. Chem. 2005, 690: 3790

17i Kondolff I. Doucet H. Santelli M. Eur. J. Org. Chem. 2006, 765