Synthesis 2017; 49(01): 188-194
DOI: 10.1055/s-0035-1561615
paper
© Georg Thieme Verlag Stuttgart · New York

Chromium-Catalyzed Cross-Coupling Reactions of Alkylmagnesium Reagents with Halo-Quinolines and Activated Aryl Chlorides

Andreas B. Bellan
Department of Chemistry, Ludwig-Maximilians-Universität München, Butenandtstrasse 5-13, Haus F, 81377 München, Germany   Email: paul.knochel@cup.uni-muenchen.de
,
Olesya M. Kuzmina
Department of Chemistry, Ludwig-Maximilians-Universität München, Butenandtstrasse 5-13, Haus F, 81377 München, Germany   Email: paul.knochel@cup.uni-muenchen.de
,
Violeta A. Vetsova
Department of Chemistry, Ludwig-Maximilians-Universität München, Butenandtstrasse 5-13, Haus F, 81377 München, Germany   Email: paul.knochel@cup.uni-muenchen.de
,
Paul Knochel*
Department of Chemistry, Ludwig-Maximilians-Universität München, Butenandtstrasse 5-13, Haus F, 81377 München, Germany   Email: paul.knochel@cup.uni-muenchen.de
› Author Affiliations
Further Information

Publication History

Received: 01 March 2016

Accepted after revision: 14 March 2016

Publication Date:
27 April 2016 (online)


Dedicated to Professor Dieter Enders on the occasion of his 70th birthday and in recognition of his outstanding contribution to asymmetric catalysis.

Abstract

An efficient protocol for chromium(III)-catalyzed C(sp2)–C(sp3) cross-coupling is reported. The alkylations of halo-quinoline and phenacyl derivatives proceed at room temperature within minutes using the tetrahydrofuran-soluble chromium(III) complex CrCl3·3THF. The reactions occur without the formation of homo-coupling side products, which are common for the related iron-, cobalt- or manganese-catalyzed cross-coupling reactions.

Supporting Information

 
  • References

  • 1 Bolm C, Legros J, Le Paih J, Zani L. Chem. Rev. 2004; 104: 6217
  • 2 Bauer I, Knölker H.-J. Chem. Rev. 2015; 115: 3170
  • 3 Kuzmina OM, Steib AK, Moyeaux A, Cahiez G, Knochel P. Synthesis 2015; 47: 1696
  • 4 Bedford RB, Gallagher T, Pye DR, Savage W. Synthesis 2015; 47: 1761
  • 5 Cahiez G, Moyeux A. Chem. Rev. 2010; 110: 1435
  • 6 Röse P, Hilt G. Synthesis 2016; 48: 463
  • 7 Hammann JM, Haas D, Steib AK, Knochel P. Synthesis 2015; 47: 1461
  • 8 Thapa S, Kafle A, Gurung S, Montoya A, Riedel P, Giri R. Angew. Chem. Int. Ed. 2015; 54: 8236
  • 9 Chen Y.-A, Badsara SS, Tsai W.-T, Lee C.-F. Synthesis 2015; 47: 181
  • 10 Steib AK, Kuzmina OM, Fernandez S, Flubacher D, Knochel P. J. Am. Chem. Soc. 2013; 135: 15346
  • 11 Steib AK, Kuzmina OM, Fernandez S, Malhotra S, Knochel P. Chem. Eur. J. 2015; 21: 1961
  • 12 Cong X, Tang H, Zeng X. J. Am. Chem. Soc. 2015; 137: 14367
  • 13 Kuzmina OM, Knochel P. Org. Lett. 2014; 16: 5208
  • 14 Steib AK, Fernandez S, Kuzmina OM, Corpet M, Gosmini C, Knochel P. Synlett 2015; 26: 1049
  • 15 Kern RJ. J. Inorg. Nucl. Chem. 1962; 24: 1105
  • 16 Piller FM, Appukkuttan P, Gavryushin A, Helm M, Knochel P. Angew. Chem. Int. Ed. 2008; 47: 6802
  • 17 Small amounts of the reduced dechlorinated coupling products were obtained as side products (up to 17%, depending on the Grignard reagent).
  • 18 Clark JS, Romiti F. Angew. Chem. Int. Ed. 2013; 52: 10072