Heck Arylation of Styrenes Promoted
by an Air-Stable Phosphinito Complex with Palladium(II); Synthesis
of Resveratrol

José Antonio Morales-Serna; Armando Zúñiga-Martínez; Manuel Salmón; Rubén Gaviño; Jorge Cárdenas

doi:10.1055/s-0031-1289664

PAPER

Heck Arylation of Styrenes Promoted by an Air-Stable Phosphinito Complex with Palladium(II); Synthesis of Resveratrol

José Antonio Morales-Serna, Armando Zúñiga-Martínez, Manuel Salmón, Rubén Gaviño, Jorge Cárdenas*
Instituto de Química, Universidad Nacional Autónoma de México Circuito Exterior, Ciudad Universitaria, Coyoacán 04510, México, D.F., México
Fax: +52(55)56162217; e-Mail: rjcp@unam.mx;

Abstract

Alle Artikel dieser Rubrik

Abstract

An air-stable phosphinito complex of palladium(II) was found to be an efficient catalyst in the Heck reaction of a variety of aryl halides and styrenes. Resveratrol was concisely synthesized in 63% overall yield; the reactions were performed under conventional and microwave heating.

Key words

Heck reaction - palladium - homogeneous catalysis - halides - coupling

Volltext

Referenzen

References

1a Hart J. Annu. Rev. Phytopathol. 1991, 19: 437

1b Jang M. Cai L. Udeani GO. Slowing KV. Thomas CF. Beecher CWW. Fong HHS. Farnsworth NR. Kinghorn AD. Mehta RG. Moon RC. Pezzuto JM. Science 1997, 275: 218

1c Burns J. Yokota T. Ashihara H. Lean MEJ. Crozier A. J. Agric. Food Chem. 2002, 50: 3337

1d Kim S. Ko H. Park JE. Jung S. Lee SK. Chun YJ. J. Med. Chem. 2002, 45: 160

1e Pettit GR. Grealish MP. Jung MK. Hamel E. Pettit RK. Chapuis JCh. Schmidt JM. J. Med. Chem. 2002, 45: 2534

1f Ohguchi K. Tanaka T. Kido T. Baba K. Linuma M. Matsumoto K. Akao Y. Nozawa Y. Biochem. Biophys. Res. Commun. 2003, 307: 861

1g de la Lastra CA. Villegas I. Mol. Nutr. Food Res. 2005, 49: 405

2a Goldberg DM. Clin. Chem. (Washington, DC., U. S.) 1995, 41: 14

2b Mattivi F. Reniero F. Korhammer S.
J. Agric. Food Chem. 1995, 43: 1820

3a Langcake P. Pryce RJ. Phytochemistry 1977, 16: 1193

3b Langcake P. Pryce CA. Physiol. Plant Pathol. 1976, 9: 77

3c Threlfall RT. Morris JR. Mauromoustakos A. Am. J. Enol. Vitic. 1999, 50: 57

4 Renaud S. De Lorgeril M. Lancet 1992, 339: 1523

5a Arichi H. Kimura Y. Okuda H. Baba K. Kozawa M. Arichi S. Chem. Pharmacol. Bull. 1982, 30: 1766

5b Babich H. Reisbaum AG. Zuckerbraun HL. Toxicol. Lett. 2000, 114: 143

6a Marambaud P. Zhao H. Davies P. J. Biol. Chem. 2005, 280: 37377

6b Anekonda TS. Brain Res. Rev. 2006, 52: 316

7 Wang ZR. Huang YZ. Zou JC. Cao KJ. Xu YN. Wu JM. Int. J. Mol. Med. 2002, 9: 77

8a Manila E. Talvitie A. Kolehmainen E. Phytochemistry 1993, 33: 813

8b Fontecave M. Lepoivre M. Elleingand E. Gerez C. Guitter O. FEBS Lett. 1998, 421: 277

8c Mgbonyebi O. Russo J. Russo I. Int. J. Oncol. 1998, 12: 865

8d Schneider Y. Vincent F. Duranton B. Badolo L. Gossé F. Bergmann C. Seiler N. Raul F. Cancer Lett. 2000, 158: 85

8e Roberti M. Pizzirani D. Simoni D. Rondanin R. Baruchello R. Bonora C. Buscemi F. Grimaudo S. Tolomeo M.
J. Med. Chem. 2003, 46: 3546

8f Wang Y. Lee KW. Chan FL. Chen S. Leung LK. Toxicol. Sci. 2006, 92: 71

9a Gehm BD. McAndrews JM. Chien PY. Jameson JL. Proc. Natl. Acad. Sci. U.S.A. 1997, 94: 14138

9b Bowers JL. Tyulmenkov W. Jernigan SC. Klinge CM. Endocrinology 2000, 141: 3657

10 Kimura Y. Okuda H. Arichi S. Biochim. Biophys. Acta 1985, 834: 275

11 Docherty JJ. Fu MMH. Stiffler BS. Limperos RJ. Pokabla CM. DeLucia AL. Antiviral Res. 1999, 43: 145

12a Jang DS. Kang BS. Ryu SY. Chang IM. Min KR. Kim Y. Biochem. Pharmacol. 1999, 57: 705

12b Stivala LA. Savio M. Carafoli F. Perucca P. Bianchi L. Maga G. Forti L. Pagoni UM. Albini A. Prosperi E. Vannini V. J. Biol. Chem. 2001, 276: 22586

12c Lee HJ. Seo JW. Lee BH. Chunga KH. Chi DY. Bioorg. Med. Chem. Lett. 2004, 14: 463

12d Shang YJ. Qian YP. Liu XD. Dai F. Shang XL. Jia WQ. Liu Q. Fang JG. Zhou B. J. Org. Chem. 2009, 74: 5025

13 Ferré-Filmon K. Delaude L. Demonceau A. Noels AF. Coord. Chem. Rev. 2004, 248: 21

14a Rao VP. Jen AKY. Wong KY. Drost KJ. Tetrahedron Lett. 1993, 34: 1747

14b Orsini F. Pelizzoni F. Verotta L. Aburjai T. Rogers CB. J. Nat. Prod. 1997, 60: 1082

14c Raimundo JM. Blanchard P. Ledoux-Rak I. Hierle R. Michaux L. Roncali J. Chem. Commun. 2000, 1597

14d Ventelon L. Charier S. Moreaux L. Mertz J. Blanchard-Desce M. Angew. Chem. Int. Ed. 2001, 40: 2098

14e Alonso F. Riente P. Yus M. Eur. J. Org. Chem. 2009, 6034

14f Alonso F. Riente P. Yus M. Tetrahedron Lett. 2009, 50: 3070

14g Kang SS. Cuendet MCD. Endringer V. Croy L. Pezzuto JM. Liptona MA. Bioorg. Med. Chem. 2009, 17: 1044

15 McNulty J. Das P. Eur. J. Org. Chem. 2009, 40: 4031

16a Meier H. Dullweber U. Tetrahedron Lett. 1996, 37: 1191

16b Wang M. Jin Y. Ho CT. J. Agric. Food Chem. 1999, 47: 3974

16c Díez-Barra E. García-Martímez JC. Rodriguez-Lopez J. Tetrahedron Lett. 1999, 40: 8181

17a Guiso M. Marra C. Farina A. Tetrahedron Lett. 2002, 43: 597

17b Andrus MB. Liu J. Meredith EL. Nartey E. Tetrahedron Lett. 2003, 44: 4819

17c Nájera C. Botella L. Tetrahedron 2004, 60: 5563

17d Yamada YMA. Takeda K. Takahashi H. Ikegami S. Tetrahedron 2004, 60: 4097

17e Farina A. Ferranti C. Marra C. Nat. Prod. Res. 2006, 20: 247

17f Cross GG. Eisnor CR. Gossage RA. Jenkins HA. Tetrahedron Lett. 2006, 47: 2245

17g Farina A. Ferranti C. Marra C. Guiso M. Norcia G. Nat. Prod. Res. 2007, 21: 564

17h Nájera C. Alacid E. ARKIVOC 2008, (viii): 50

17i Moro AV. Cardoso FSP. Correia CRD. Tetrahedron Lett. 2008, 49: 5668

18 Bazin M.-A. Kihel LE. Lancelot J.-C. Rault S. Tetrahedron Lett. 2007, 48: 4347

19a Chang S. Na Y. Shin HJ. Choi E. Jeong LS. Tetrahedron Lett. 2002, 43: 7445

19b Ferre-Filmon K. Delaude L. Demonceau A. Noels AF. Eur. J. Org. Chem. 2005, 3319

19c Velder J. Ritter S. Lex J. Schmalz H.-G. Synthesis 2006, 273

20a Solladié G. Pasturel-Jacopé Y. Maignan J. Tetrahedron 2003, 59: 3315

20b Kumar V. Sharma A. Sharma A. Sinha AK. Tetrahedron 2007, 63: 7640

20c Sinha AK. Kumar V. Sharma A. Sharma A. Kumar R. Tetrahedron 2007, 63: 11070

21 Hilt G. Hengst C. J. Org. Chem. 2007, 72: 7337

22 Robinson JE. Taylor RJK. Chem. Commun. 2007, 1617

23a Alonso E. Ramón DJ. Yus M. J. Org. Chem. 1997, 62: 417

23b Polunin KE. Schmalz HG. Polunina IA. Russ. Chem. Bull. 2002, 51: 1319

24 Sauza A. Morales-Serna JA. García-Molina M. Gaviño R. Cárdenas J. Synthesis 2012, 44: 272

25 Jiménez-Bülle J. Gaviño R. Catal. Commun. 2008, 9: 826

26 Dixon KR. Rattray AD. Can. J. Chem. 1971, 49: 3997

27a Ghaffar T. Kieszkiewicz A. Nyburg SC. Parkins AW. Acta Crystallogr., Sect. C 1994, 50: 697

27b Gebauer T. Frenzen G. Dehnicke K. Z. Kristallogr. 1995, 210: 539

27c Bergamini P. Bertolasi V. Cattabriga M. Ferretti V. Loprieno U. Mantovani N. Marvelli L. Eur. J. Inorg. Chem. 2003, 5: 918

28 Pryjomska I. Bartoz-Bechowsky H. Ciunik Z. Trzeciak AM. Ziólkowski JJ. J. Chem.Soc., Dalton Trans. 2006, 213

29 Thorn MA. Denny GH. Babson RD. J. Org. Chem. 1975, 40: 1556

30 Mao W. Wang T. Zeng H. Wang Z. Chen J. Shen J. Bioorg. Med. Chem. Lett. 2009, 19: 4570

31 Jeffery T. Ferber B. Tetrahedron Lett. 2003, 44: 193

32a Cui X. Li Z. Tao C.-Z. Xu Y. Li J. Liu L. Guo Q.-X. Org. Lett. 2006, 8: 2467

32b Huang S.-H. Chen J.-R. Tsai F.-Y. Molecules 2010, 15: 315

33 Mariampillai B. Alberico D. Bidau V. Lautens M.
J. Am. Chem. Soc. 2006, 128: 14436