An N-heterocyclic carbene ligand with flexible steric bulk allows Suzuki cross-coupling of sterically hindered aryl chlorides at room temperature

Angewandte Chemie - International Edition

Volumn 42, Issue 31, 2003, Pages 3690-3693

  Altenhoff, Gereon ^a   Goddard, Richard ^a   Lehmann, Christian W ^a   Glorius, Frank ^a  

^a MAX PLANCK INSTITUT FÜR KOHLENFORSCHUNG   (Germany)

Author keywords

Biaryls; C C coupling; Carbene ligands; Cross coupling; Palladium

Indexed keywords

CATALYSTS; OXIDATION; PALLADIUM;

CROSS-COUPLING;

STEREOCHEMISTRY;

CARBENE; CHLORINE DERIVATIVE; HETEROCYCLIC COMPOUND; LIGAND; PALLADIUM;

ADDITION REACTION; ARTICLE; CHEMICAL BINDING; CHEMICAL REACTION KINETICS; CHEMICAL STRUCTURE; ELIMINATION REACTION; LIGAND BINDING; METAL BINDING; OXIDATION; REACTION ANALYSIS; REDUCTION; ROOM TEMPERATURE; STEREOCHEMISTRY; STEREOSPECIFICITY; STRUCTURE ANALYSIS; SUZUKI CROSS COUPLING;

EID: 0042969355     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200351325     Document Type: Article

References (40)

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26. 0 complexes as catalytically active species in Suzuki cross-coupling has been proposed; for example, see: a) reference [3c]; b) reference [3d]; c) Q.-S. Hu, Y. Lu, Z.-Y. Tang, H.-B. Yu, J. Am. Chem. Soc. 2003, 125, 2856.
27. 0 complexes as catalytically active species in Suzuki cross-coupling has been proposed; for example, see: a) reference [3c]; b) reference [3d]; c) Q.-S. Hu, Y. Lu, Z.-Y. Tang, H.-B. Yu, J. Am. Chem. Soc. 2003, 125, 2856.
28. 0 complexes as catalytically active species in Suzuki cross-coupling has been proposed; for example, see: a) reference [3c]; b) reference [3d]; c) Q.-S. Hu, Y. Lu, Z.-Y. Tang, H.-B. Yu, J. Am. Chem. Soc. 2003, 125, 2856.
29. For the synthesis of sterically hindered biaryl compounds by Suzuki cross-coupling at elevated temperatures, see: a) reference [3b]; b) reference [3c]; c) J. Yin, M. P. Rainka, X.-X. Zhang, S. L. Buchwald, J. Am. Chem. Soc. 2002, 124, 1162.
30. For the synthesis of sterically hindered biaryl compounds by Suzuki cross-coupling at elevated temperatures, see: a) reference [3b]; b) reference [3c]; c) J. Yin, M. P. Rainka, X.-X. Zhang, S. L. Buchwald, J. Am. Chem. Soc. 2002, 124, 1162.
31. For the synthesis of sterically hindered biaryl compounds by Suzuki cross-coupling at elevated temperatures, see: a) reference [3b]; b) reference [3c]; c) J. Yin, M. P. Rainka, X.-X. Zhang, S. L. Buchwald, J. Am. Chem. Soc. 2002, 124, 1162.
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34. -3.
35. -3.
36. 2 (SHELXL-97); both programs from: G. Sheldrick, University of Göttingen, 1997; CCDC-204549 (4) and CCDC-204550 (5·THF) contain the crystallographic data (excluding structure factors) for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk/conts/retrieving.html (or from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB21EZ, UK; fax: (+44) 1223-336-033; or e-mail: deposit@ccdc.cam.ac.uk).
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38. All new compounds were fully characterized.
39. A beneficial effect of increasing the ligand/Pd ratio was also observed by Buchwald and co-workers for Pd-phosphane-catalyzed cross-coupling reactions of sterically hindered substrates.[3b]
40. 2] the angle between the imidazolylidene ligands is 84.4(2)°, whereas in 5 it is 62(1)° (mean), despite a significantly shorter Pd-C distance (2.001(2) relative to 2.076(5) Å).[14a]