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
Synthesis 2010(15): 2621-2625
DOI: 10.1055/s-0029-1218848
DOI: 10.1055/s-0029-1218848
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New York
Tandem Suzuki-Miyaura Cross-Coupling/Dehydrobromination of 1,1-Dibromoalkenes to Alkynes with a Cyclobutene-1,2-diylbis(imidazolium) Salt as Catalyst Precursor
Weitere Informationen
Received
17 February 2010
Publikationsdatum:
25. Juni 2010 (online)
Publikationsverlauf
Publikationsdatum:
25. Juni 2010 (online)
![](https://www.thieme-connect.de/media/synthesis/201015/lookinside/thumbnails/10.1055-s-0029-1218848-1.jpg)
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
-
1a
Modern Acetylene Chemistry
Stang PJ.Diederich F. VCH; Weinheim: 1995. -
1b
Acetylene
Chemistry: Chemistry, Biology and Material Science
Diederich F.Stang PJ.Tykwinski RR. Wiley-VCH; Weinheim: 2005. -
2a
Science of Synthesis
Hopf H.Thomas E. Vol. 43; Thieme: Stuttgart: 2008. -
2b
Methoden
der Organischen Chemie, Houben-Weyl
Vol. 5/2a:
Müller E. Thieme; Stuttgart: 1977. -
3a
Gleiter R.Merger R. In Modern Acetylene ChemistryStang PJ.Diederich E. VCH; Weinheim: 1995. p.285 -
3b
Gleiter R. Angew. Chem., Int. Ed. Engl. 1992, 31: 27 ; Angew. Chem. 1992, 104, 29 -
3c
Krebs A.Wilke J. Top. Curr. Chem. 1983, 109: 189 -
3d
Nakagawa M. In The Chemistry of the Carbon-Carbon Triple BondPatai S. Wiley; New York: 1978. p.635 -
4a
Hopf H. Asian Chem. Lett. 2007, 11: 153 -
4b
Kivala M.Diederich F. Pure Appl. Chem. 2008, 80: 411 - 5
Organic
Electronic Materials
Farchiono R.Grosso G. Springer; Berlin: 2001. - 6
Shi Shun ALK.Tykwinski RR. Angew. Chem. Int. Ed. 2006, 45: 1034 ; Angew. Chem. 2006, 118, 1050 -
7a
Sankararaman S. In Science of Synthesis Vol. 43:Hopf H.Thomas E. Thieme; Stuttgart: 2008. p.435 -
7b
Brandsma L. Preparative Acetylenic Chemistry, 2nd ed. Elsevier; Amsterdam: 1988. -
7c
Viehe HG. Chemistry of Acetylenes Marcel Dekker; New York: 1969. -
7d
Ben-Efraim DA. In The Chemistry of the Carbon-Carbon Triple BondPatai S. Wiley; New York: 1978. p.755 -
8a
Schobert R.Gordon GJ. In Science of Synthesis Vol. 27:Padwa A. Thieme; Stuttgart: 2004. p.973 -
8b
Corey EJ.Fuchs PL. Tetrahedron Lett. 1972, 3769 - 9
Ratovelomanana V.Rollin Y.Gébéhenne C.Gosmini C.Périchon J. Tetrahedron Lett. 1994, 35: 4777 -
10a
Molander GA.Yokoyama Y. J. Org. Chem. 2006, 71: 2493 -
10b
Kabalka GW.Dong G.Venkataiah B. Tetrahedron Lett. 2005, 46: 763 -
10c
Bauer A.Miller MW.Susan FV.McCombie SW. Synlett 2001, 254 -
10d
Shen W. Synlett 2000, 737 -
10e
Roush WR.Reilly ML.Kayama K.Brown BB. J. Org. Chem. 1997, 62: 8708 -
10f
Baldwin JE.Chesworth R.Parker JSP.Russel AT. Tetrahedron Lett. 1995, 36: 9551 -
10g
Roush WR.Moriarty KJ.Brown BB. Tetrahedron Lett. 1990, 31: 6509 -
10h
Roush WR.Brown BB.Drozda SE. Tetrahedron Lett. 1988, 29: 3541 -
11a
Chelucci G.Capitta F.Baldino S.Pinna GA. Tetrahedron Lett. 2007, 48: 6514 -
11b
Chelucci G.Capitta F.Baldino S. Tetrahedron 2008, 64: 10250 -
12a
Jacobsen MF.Moses JE.Adlington RM.Baldwin JE. Org. Lett. 2005, 7: 641 -
12b
Jacobsen MF.Moses JE.Adlington RM.Baldwin JE. Tetrahedron 2006, 62: 1675 - 13
Shen W.Wang L. J. Org. Chem. 1999, 64: 8873 -
14a
Olivo HF.Velázquez F.Trevisan HC. Org. Lett. 2000, 2: 4055 -
14b
Trost BM.Dirat O.Gunzner JL. Angew. Chem. Int. Ed. 2002, 41: 841 ; Angew. Chem. 2002, 114, 869 -
14c
Trost BM.Gunzner JL.Dirat O.Rhee YH. J. Am. Chem. Soc. 2002, 124: 10396 -
14d
Huang H.Panek JS. Org. Lett. 2004, 6: 4383 -
14e
Centonze-Audureau S.Porée F.-H.Betzer J.-F.Brion J.-D.Pancrazi A.Ardisson J. Synlett 2005, 981 -
14f
Arai N.Miyaoku T.Teruya S.Mori A. Tetrahedron Lett. 2008, 49: 1000 -
15a
Schmidt A.Münster N.Dreger A. Angew. Chem. Int. Ed. 2010, 49: 2790 ; Angew. Chem. 2010, 122, 2851 -
15b
Scherbakow S.Namyslo JC.Gjikaj M.Schmidt A. Synlett 2009, 1964 -
15c
Schmidt A.Snovydovych B. Synthesis 2008, 2798 -
15d
Schmidt A.Snovydovych B.Hemmen S. Eur. J. Org. Chem. 2008, 4313 -
15e
Schmidt A.Beutler A.Albrecht M.Ramírez FJ. Org. Biomol. Chem. 2008, 6: 287 -
15f
Schmidt A.Snovydovych B.Habeck T.Dröttboom P.Gjikaj M.Adam A. Eur. J. Org. Chem. 2007, 4909 -
15g
Schmidt A.Habeck T.Snovydovych B.Eisfeld W. Org. Lett. 2007, 9: 3515 - 16
Schmidt A.Rahimi A. Chem. Commun. 2010, 46: 2995 - 17
Desai NB.McKelvie N.Ramirez F. J. Am. Chem. Soc. 1962, 84: 1745 - 18
Bestmann HJ.Frey H. Liebigs Ann. Chem. 1980, 12: 2061 - 19
Lok WN.Ward AD. Aust. J. Chem. 1978, 31: 617 - 20
Quesada E.Raw SA.Reid M.Roman E.Taylor RJK. Tetrahedron 2006, 62: 6673 - 21
Lipshutz BH.Chung DW.Rich B. Org. Lett. 2008, 10: 3793 -
22a
Moon J.Jang M.Lee S. J. Org. Chem. 2009, 74: 1403 -
22b
Dhudshia B.Thadani AN. Chem. Commun. 2006, 668 - 23
Savarin C.Srogl J.Liebeskind LS. Org. Lett. 2001, 3: 91 - 24
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