Tandem Suzuki-Miyaura
Cross-Coupling/Dehydrobromination of 1,1-Dibromoalkenes
to Alkynes with a Cyclobutene-1,2-diylbis(imidazolium) Salt as Catalyst
Precursor

Alireza Rahimi; Andreas Schmidt

doi:10.1055/s-0029-1218848

PAPER

Tandem Suzuki-Miyaura Cross-Coupling/Dehydrobromination of 1,1-Dibromoalkenes to Alkynes with a Cyclobutene-1,2-diylbis(imidazolium) Salt as Catalyst Precursor

Alireza Rahimi, Andreas Schmidt*
Clausthal University of Technology, Institute of Organic Chemistry, Leibnizstr. 6, 38678 Clausthal-Zellerfeld, Germany
Fax: +49(5323)723861; e-Mail: schmidt@ioc.tu-clausthal.de;

Abstract

Alle Artikel dieser Rubrik

Abstract

A cyclobutene-1,2-bis(imidazolium) salt proved to be an efficient catalyst precursor for one-pot tandem Suzuki-Miyaura/dehydrobromination reactions for the synthesis of alkynes starting from 1,1-dibromoalkenes and palladium(II) acetate, aryl boronic acids, and potassium tert-butoxide in toluene. Starting materials were prepared from aldehydes under Corey-Fuchs conditions.

Key words

imidazol-2-ylidene - N-heterocyclic carbene - biscarbene complex - Corey-Fuchs reaction

Volltext

Referenzen

References

<A NAME="RT03910SS-1A">1a</A> Modern Acetylene Chemistry Stang PJ. Diederich F. VCH; Weinheim: 1995.

<A NAME="RT03910SS-1B">1b</A> Acetylene Chemistry: Chemistry, Biology and Material Science Diederich F. Stang PJ. Tykwinski RR. Wiley-VCH; Weinheim: 2005.

<A NAME="RT03910SS-2A">2a</A> Science of Synthesis Hopf H. Thomas E. Vol. 43; Thieme: Stuttgart: 2008.

<A NAME="RT03910SS-2B">2b</A> Methoden der Organischen Chemie, Houben-Weyl Vol. 5/2a: Müller E. Thieme; Stuttgart: 1977.

<A NAME="RT03910SS-3A">3a</A> Gleiter R. Merger R. In Modern Acetylene Chemistry Stang PJ. Diederich E. VCH; Weinheim: 1995. p.285

<A NAME="RT03910SS-3B">3b</A> Gleiter R. Angew. Chem., Int. Ed. Engl. 1992, 31: 27 ; Angew. Chem. 1992, 104, 29

<A NAME="RT03910SS-3C">3c</A> Krebs A. Wilke J. Top. Curr. Chem. 1983, 109: 189

<A NAME="RT03910SS-3D">3d</A> Nakagawa M. In The Chemistry of the Carbon-Carbon Triple Bond Patai S. Wiley; New York: 1978. p.635

<A NAME="RT03910SS-4A">4a</A> Hopf H. Asian Chem. Lett. 2007, 11: 153

<A NAME="RT03910SS-4B">4b</A> Kivala M. Diederich F. Pure Appl. Chem. 2008, 80: 411

<A NAME="RT03910SS-5">5</A> Organic Electronic Materials Farchiono R. Grosso G. Springer; Berlin: 2001.

<A NAME="RT03910SS-6">6</A> Shi Shun ALK. Tykwinski RR. Angew. Chem. Int. Ed. 2006, 45: 1034 ; Angew. Chem. 2006, 118, 1050

<A NAME="RT03910SS-7A">7a</A> Sankararaman S. In Science of Synthesis Vol. 43: Hopf H. Thomas E. Thieme; Stuttgart: 2008. p.435

<A NAME="RT03910SS-7B">7b</A> Brandsma L. Preparative Acetylenic Chemistry, 2nd ed. Elsevier; Amsterdam: 1988.

<A NAME="RT03910SS-7C">7c</A> Viehe HG. Chemistry of Acetylenes Marcel Dekker; New York: 1969.

<A NAME="RT03910SS-7D">7d</A> Ben-Efraim DA. In The Chemistry of the Carbon-Carbon Triple Bond Patai S. Wiley; New York: 1978. p.755

<A NAME="RT03910SS-8A">8a</A> Schobert R. Gordon GJ. In Science of Synthesis Vol. 27: Padwa A. Thieme; Stuttgart: 2004. p.973

<A NAME="RT03910SS-8B">8b</A> Corey EJ. Fuchs PL. Tetrahedron Lett. 1972, 3769

<A NAME="RT03910SS-9">9</A> Ratovelomanana V. Rollin Y. Gébéhenne C. Gosmini C. Périchon J. Tetrahedron Lett. 1994, 35: 4777

<A NAME="RT03910SS-10A">10a</A> Molander GA. Yokoyama Y. J. Org. Chem. 2006, 71: 2493

<A NAME="RT03910SS-10B">10b</A> Kabalka GW. Dong G. Venkataiah B. Tetrahedron Lett. 2005, 46: 763

<A NAME="RT03910SS-10C">10c</A> Bauer A. Miller MW. Susan FV. McCombie SW. Synlett 2001, 254

<A NAME="RT03910SS-10D">10d</A> Shen W. Synlett 2000, 737

<A NAME="RT03910SS-10E">10e</A> Roush WR. Reilly ML. Kayama K. Brown BB. J. Org. Chem. 1997, 62: 8708

<A NAME="RT03910SS-10F">10f</A> Baldwin JE. Chesworth R. Parker JSP. Russel AT. Tetrahedron Lett. 1995, 36: 9551

<A NAME="RT03910SS-10G">10g</A> Roush WR. Moriarty KJ. Brown BB. Tetrahedron Lett. 1990, 31: 6509

<A NAME="RT03910SS-10H">10h</A> Roush WR. Brown BB. Drozda SE. Tetrahedron Lett. 1988, 29: 3541

<A NAME="RT03910SS-11A">11a</A> Chelucci G. Capitta F. Baldino S. Pinna GA. Tetrahedron Lett. 2007, 48: 6514

<A NAME="RT03910SS-11B">11b</A> Chelucci G. Capitta F. Baldino S. Tetrahedron 2008, 64: 10250

<A NAME="RT03910SS-12A">12a</A> Jacobsen MF. Moses JE. Adlington RM. Baldwin JE. Org. Lett. 2005, 7: 641

<A NAME="RT03910SS-12B">12b</A> Jacobsen MF. Moses JE. Adlington RM. Baldwin JE. Tetrahedron 2006, 62: 1675

<A NAME="RT03910SS-13">13</A> Shen W. Wang L. J. Org. Chem. 1999, 64: 8873

<A NAME="RT03910SS-14A">14a</A> Olivo HF. Velázquez F. Trevisan HC. Org. Lett. 2000, 2: 4055

<A NAME="RT03910SS-14B">14b</A> Trost BM. Dirat O. Gunzner JL. Angew. Chem. Int. Ed. 2002, 41: 841 ; Angew. Chem. 2002, 114, 869

<A NAME="RT03910SS-14C">14c</A> Trost BM. Gunzner JL. Dirat O. Rhee YH. J. Am. Chem. Soc. 2002, 124: 10396

<A NAME="RT03910SS-14D">14d</A> Huang H. Panek JS. Org. Lett. 2004, 6: 4383

<A NAME="RT03910SS-14E">14e</A> Centonze-Audureau S. Porée F.-H. Betzer J.-F. Brion J.-D. Pancrazi A. Ardisson J. Synlett 2005, 981

<A NAME="RT03910SS-14F">14f</A> Arai N. Miyaoku T. Teruya S. Mori A. Tetrahedron Lett. 2008, 49: 1000

<A NAME="RT03910SS-15A">15a</A> Schmidt A. Münster N. Dreger A. Angew. Chem. Int. Ed. 2010, 49: 2790 ; Angew. Chem. 2010, 122, 2851

<A NAME="RT03910SS-15B">15b</A> Scherbakow S. Namyslo JC. Gjikaj M. Schmidt A. Synlett 2009, 1964

<A NAME="RT03910SS-15C">15c</A> Schmidt A. Snovydovych B. Synthesis 2008, 2798

<A NAME="RT03910SS-15D">15d</A> Schmidt A. Snovydovych B. Hemmen S. Eur. J. Org. Chem. 2008, 4313

<A NAME="RT03910SS-15E">15e</A> Schmidt A. Beutler A. Albrecht M. Ramírez FJ. Org. Biomol. Chem. 2008, 6: 287

<A NAME="RT03910SS-15F">15f</A> Schmidt A. Snovydovych B. Habeck T. Dröttboom P. Gjikaj M. Adam A. Eur. J. Org. Chem. 2007, 4909

<A NAME="RT03910SS-15G">15g</A> Schmidt A. Habeck T. Snovydovych B. Eisfeld W. Org. Lett. 2007, 9: 3515

<A NAME="RT03910SS-16">16</A> Schmidt A. Rahimi A. Chem. Commun. 2010, 46: 2995

<A NAME="RT03910SS-17">17</A> Desai NB. McKelvie N. Ramirez F. J. Am. Chem. Soc. 1962, 84: 1745

<A NAME="RT03910SS-18">18</A> Bestmann HJ. Frey H. Liebigs Ann. Chem. 1980, 12: 2061

<A NAME="RT03910SS-19">19</A> Lok WN. Ward AD. Aust. J. Chem. 1978, 31: 617

<A NAME="RT03910SS-20">20</A> Quesada E. Raw SA. Reid M. Roman E. Taylor RJK. Tetrahedron 2006, 62: 6673

<A NAME="RT03910SS-21">21</A> Lipshutz BH. Chung DW. Rich B. Org. Lett. 2008, 10: 3793

<A NAME="RT03910SS-22A">22a</A> Moon J. Jang M. Lee S. J. Org. Chem. 2009, 74: 1403

<A NAME="RT03910SS-22B">22b</A> Dhudshia B. Thadani AN. Chem. Commun. 2006, 668

<A NAME="RT03910SS-23">23</A> Savarin C. Srogl J. Liebeskind LS. Org. Lett. 2001, 3: 91

<A NAME="RT03910SS-24">24</A> Wan C.-W. Burghart A. Chen J. Bergstroem F. Johansson LB.-A. Wolford MF. Kim TG. Topp MR. Hochstrasser RM. Burgess K. Chem. Eur. J. 2003, 9: 4430