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

Andreas B. Bellan; Olesya M. Kuzmina; Violeta A. Vetsova; Paul Knochel

doi:10.1055/s-0035-1561615

Synthesis, Table of Contents

Synthesis 2017; 49(01): 188-194
DOI: 10.1055/s-0035-1561615

paper

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

Authors

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

Abstract

All articles of this category

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.

Key words

magnesium - chromium - quinolines - cross-coupling - Grignard reagents

Full Text

References

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

Supplementary Material

Supporting Information (PDF)