A Convenient One-Pot Synthesis
of Bis[(E)-4-halostyryl]arene
Derivatives

Wiesław Prukała; Mariusz Majchrzak; Krystian Posała; Bogdan Marciniec

doi:10.1055/s-2008-1067253

RSS-Feed abonnieren

Bitte kopieren Sie die angezeigte URL und fügen sie dann in Ihren RSS-Reader ein.

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

Teilen / Bookmarken

Facebook X Linkedin Weibo

PDF herunterladen

Synthesis 2008(19): 3047-3052
DOI: 10.1055/s-2008-1067253

PAPER

A Convenient One-Pot Synthesis of Bis[(E)-4-halostyryl]arene Derivatives

Wiesław Prukała, Mariusz Majchrzak, Krystian Posała, Bogdan Marciniec*
Department of Organometallic Chemistry, Faculty of Chemistry, Adam Mickiewicz University, Grunwaldzka 6, 60-780 Poznan, Poland
Fax: +48(61)8291508; e-Mail: marcinb@amu.edu.pl;

Weitere Informationen

Publikationsverlauf

Received 17 March 2008
Publikationsdatum:
04. September 2008 (online)

Abstract
Volltext
Referenzen

Artikel einzeln kaufen Lizenzen und Reprints Alle Artikel dieser Rubrik

Abstract

A new convenient synthetic protocol for the one-pot stereoselective synthesis of bis[(E)-4-bromo(or chloro)styryl]arene derivatives via the sequential reaction of silylative-coupling of 4-halostyrenes with vinylsilanes followed by palladium-catalyzed cross-coupling 4-halostyrylsilanes with diiodoarenes, is described. The reaction leads to symmetrical bis[(E)-4-halostyryl]arene derivatives obtained in a stereocontrolled manner with high efficiency.

Key words

vinylsilanes - transition metals catalysis - silylative cross-coupling

References

1a Special issue: Molecular Materials in Electronic and Optoelectronic Devices Sheats JR. Barbara PF. Acc. Chem. Res. 1999. 32: p.191-276
1b Videlot-Ackermann C. Ackermann J. Brisset H. Kawamura K. Yoshimoto N. Raynal P. El Kassmi A. Fages F. J. Am. Chem. Soc. 2005, 127: 16346

Suche in Google Scholar
1c Wilson JN. Bunz UHF. J. Am. Chem. Soc. 2005, 127: 4124

Suche in Google Scholar
1d Takeshi T, and Takaaki I. inventors; European Patent EP 1 843 211.
2 Meier H. Angew. Chem., Int. Ed. Engl. 1992, 31: 1399

Crossref Suche in Google Scholar
3a Weitzel HP. Müllen K. Makromol. Chem. 1990, 13: 563

Suche in Google Scholar
3b Suzuki M. Lim JC. Saegusa T. Macromolecules 1990, 23: 1574

Suche in Google Scholar
3c Scherf U. Mullen K. Synthesis 1992, 23 ; and literature cited therein
3d Katayama H. Nagao M. Nishimura T. Matsui Y. Umeda K. Akamatsu K. Tsuruoka T. Nawafune H. Ozawa F. J. Am. Chem. Soc. 2005, 127: 4350

Suche in Google Scholar
3e Katayama H. Nagao M. Ozawa F. Ikegami M. Arai T. J. Org. Chem. 2006, 71: 2699

Suche in Google Scholar
3f Leclerc N. Sanaur S. Galmiche L. Mathevet F. Attias A.-J. Fave J.-L. Roussel J. Hapiot P. Lemaitre N. Geffroy B. Chem. Mater. 2005, 17: 502

Suche in Google Scholar
3g Egbe DAM. Tekin E. Berckner E. Pivrikas A. Sariciftci NS. Schubert US. Macromolecules 2007, 40: 7786

Suche in Google Scholar
4a Quintini M. inventors; US Patent 5 250 223.
4b Reinehr D, Sauter H, Kramer J, Weigmann R, Eckhardt C, and Meyer HR. inventors; European Patent EP 0900784.
4c Hhoaf GL, Ollis GW, Stockl RR, and Munjal RC. inventors; US Patent 0249764.
5a Frechet JM. Hawker CJ. Gitsov I. Leon JW. J. Macromol. Sci., Part A: Pure Appl. Chem. 1996, A33: 1399

Suche in Google Scholar
5b Meier H. Lehmann M. Angew. Chem. Int. Ed. 1998, 37: 643

Suche in Google Scholar
5c Lo S.-C. Burn PL. Chem. Rev. 2007, 107: 1097 ; and literature cited therein

Suche in Google Scholar
6a Friedrich K. Henning H.-G. Chem. Ber. 1959, 92: 2944

Suche in Google Scholar
6b Bontagy J. Thomas R. Chem. Rev. 1974, 74: 87

Suche in Google Scholar
6c Arient J. Collect. Czech. Chem. Commun. 1981, 46: 101

Suche in Google Scholar
6d Deb SK. Maddux TM. Yu L. J. Am. Chem. Soc. 1997, 119: 9079

Suche in Google Scholar
6e Pillow JNG. Halim M. Lupton JM. Burn PL. Samuel IDW. Macromolecules 1999, 32: 5985

Suche in Google Scholar
6f Segura JL. Gomez R. Martin N. Guldi DM. Org. Lett. 2001, 3: 2645

Suche in Google Scholar
6g Palsson L.-O. Beavington R. Frampton MJ. Lupon JM. Magennis SW. Markham JPJ. Pillow JNG. Burn PL. Samuel IDW. Macromolecules 2002, 35: 7891

Suche in Google Scholar
6h Cano-Marin AR. Diez-Barra E. Rodriguez-Lopez J. Tetrahedron 2005, 61: 395

Suche in Google Scholar
7a Sengupta S. Sadhukhan SK. Singh RS. Pal N. Tetrahedron Lett. 2002, 43: 1117

Suche in Google Scholar
7b Itami K. Tonogaki K. Nokami T. Ohashi Y. Yoshida J. Angew. Chem. Int. Ed. 2006, 45: 2404

Suche in Google Scholar
8a Katayama H. Nagao M. Nishimura T. Matsui Y. Fukuse Y. Wakioka M. Ozawa F. Macromolecules 2006, 39: 2039

Suche in Google Scholar
8b Katayama H. Nagao M. Ozawa F. Ikegami M. Arai T. J. Org. Chem. 2006, 71: 2699

Suche in Google Scholar
9a Marciniec B. Pietraszuk C. Handbook of Metathesis Vol. 2: Grubbs R. Wiley-VCH; Weinheim: 2003.

Suche in Google Scholar
9b Marciniec B. Zaidlewicz M. Pietraszuk C. Kownacki I. In Comprehensive Organic Functional Group Transformations II Vol. 2: Katritzky AR. Taylor RJK. Elsevier Science; Amsterdam: 2005. p.941-1024

Suche in Google Scholar
9c Marciniec B. Coord. Chem. Rev. 2005, 249: 2374

Suche in Google Scholar
9d Marciniec B. Acc. Chem. Res. 2007, 40: 943

Suche in Google Scholar
10a Hiyama T. In Handbook of Organopalladium Chemistry for Organic Synthesis Vol. 1: Negishi E. Wiley-Interscience; New York: 2002. p.285

Suche in Google Scholar
10b Hiyama T. In Metal-Catalyzed Cross-Coupling Reactions Diederich F. Stang PJ. Wiley-VCH; Weinheim: 1998.
10c Prukaa W. Majchrzak M. Pietraszuk C. Marciniec B. J. Mol. Catal. A: Chem. 2006, 254: 58

Suche in Google Scholar
10d Prukaa W. Pawluć P. Posaa K. Marciniec B. Synlett 2008, 41
11a Levison JJ. Robinson SD. J. Chem. Soc. A 1970, 2947
11b Ahmad N. Levison JJ. Robinson SD. Uttley MF. Inorg. Synth. 1974, 15: 45

Suche in Google Scholar
12 Ukai T. Kawazura H. Ishii Y. J. Organomet. Chem. 1974, 65: 253

Crossref Suche in Google Scholar