Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Synthesis 2009(14): 2447-2453
DOI: 10.1055/s-0029-1216829
DOI: 10.1055/s-0029-1216829
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New York
Potassium [1-(tert-Butoxycarbonyl)-1H-indol-2-yl]trifluoroborate as an Efficient Building Block in Palladium-Catalyzed Suzuki-Miyaura Cross Couplings
Further Information
Received
25 February 2009
Publication Date:
27 May 2009 (online)
Publication History
Publication Date:
27 May 2009 (online)
Abstract
Potassium [1-(tert-butoxycarbonyl)-1H-indol-2-yl]trifluoroborate (1) was used in Suzuki-type coupling reactions. First, the best coupling conditions were assessed using bromobenzene as the electrophile. Then, 1 was successfully coupled with various aryl and hetaryl bromides. Finally, the reactivity of 1 towards coupling partners other than bromide derivatives was evaluated.
Key words
Suzuki coupling - organotrifluoroborates - palladium catalysis - indoles
- 1
Daïri K.Yao Y.Faley M.Tripathy S.Rioux E.Billot X.Rabouin D.Gonzalez G.Lavallée J.-F.Attardo G. Org. Process Res. Dev. 2007, 11: 1051 - 2
Carey JS.Laffan D.Thomson C.Williams MT. Org. Biomol. Chem. 2006, 4: 2337 - 3
Blaser H.-U.Indolese A.Naud F.Nettekoven U.Schnyder A. Adv. Synth. Catal. 2004, 346: 1583 - 4
Hall DG. Boronic Acids: Preparation and Applications in Organic Synthesis and Medicine Wiley-VCH; Weinheim: 2005. - 5
Darses S.Genêt J.-P. Eur. J. Org. Chem. 2003, 4313 - 6
Molander GA.Figueroa R. Aldrichimica Acta 2005, 38: 49 - 7
Stefani HA.Cella R.Vieira AS. Tetrahedron 2007, 63: 3623 - 8
Molander GA.Ellis N. Acc. Chem. Res. 2007, 40: 275 - 9
Doucet H. Eur. J. Org. Chem. 2008, 2013 - 10
Darses S.Genêt J.-P. Chem. Rev. 2008, 108: 288 - 11
Mizuta M.Seio K.Miyata K.Sekine M. J. Org. Chem. 2007, 72: 5046 - 12
Pagano N.Maksimoska J.Bregman H.Williams DS.Webster RD.Xue F.Meggers E. Org. Biomol. Chem. 2007, 5: 1218 - 13
Vedejs E.Chapman RW.Fields SC.Lin S.Schrimpf MR. J. Org. Chem. 1995, 60: 3020 - 14
Vazquez E.Davies IW.Payack JF. J. Org. Chem. 2002, 67: 7551 - 15
Molander GA.Biolatto B. J. Org. Chem. 2003, 68: 4302 - 16
Lysen M.Köhler K. Synthesis 2006, 692 - 17
Koning CB.Michael JP.Rousseau AL. J. Chem. Soc., Perkin Trans. 1 2000, 1705 - 18
Ishikura M.Agata I.Katagiri N. J. Heterocycl. Chem. 1999, 36: 873 - 19
Liebeskind LS.Srogl J. Org. Lett. 2002, 4: 979 - 20
Kazmierski I.Gosmini C.Paris JM.Périchon J. Synlett 2006, 881 - 21
Molander GA.Canturk B.Kennedy LE. J. Org. Chem. 2009, 74: 973 - 22
Molander GA.Gormisky PE. J. Org. Chem. 2008, 73: 7481 - 23
Paudler WW.Chem IK. J. Heterocycl. Chem. 1970, 7: 767 - 24
Darses S.Michaud G.Genêt J.-P. Eur. J. Org. Chem. 1999, 1875 - 25
Sakamoto T.Kondo Y.Takazawa N.Yamanaka H. J. Chem. Soc., Perkin Trans. 1 1996, 1927 - 26
Labadie SS.Teng E. J. Org. Chem. 1994, 59: 4250 - 27
Pena MA.Sestelo JP.Sarandeses LA. J. Org. Chem. 2007, 72: 1271 - 28
Denmark SE.Baird JD. Org. Lett. 2004, 6: 3649 - 29
Kuwano R.Kashiwabara M. Org. Lett. 2006, 8: 2653 - 30
Hasan I.Marinelli ER.Chang Lin L.-C.Fowler FW.Levy AB. J. Org. Chem. 1981, 46: 157