The DOI matches its Crossref record; 3 of the 3 references it cites were found in a registry or an index.
Pd-Catalyzed Intermolecular Amidation of Aryl Halides: The Discovery that Xantphos Can Be Trans-Chelating in a Palladium Complex
Abstract
A general method for the intermolecular coupling of aryl halides and amides using a Xantphos/Pd catalyst is described. This system displays good functional group compatibility, and the desired C-N bond forming process proceeds in good to excellent yields with 1-4 mol % of the Pd catalyst. Additionally, the arylation of sulfonamides, oxazolidinones, and ureas is reported. The efficiency of these transformations was found to be highly dependent on reaction concentrations and catalyst loadings. A Pd complex resulting from oxidative addition of 4-bromobenzonitrile, (Xantphos)Pd(4-cyanophenyl)(Br) (II), was prepared in one step from Xantphos, Pd(2)(dba)(3), and the aryl bromide. Complex II proved to be an active catalyst for the coupling between 4-bromobenzonitrile and benzamide. X-ray crystallographic analysis of II revealed a rare trans-chelating bisphosphine-Pd(II) structure with a large bite angle of 150.7 degrees.
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Cites
Klapars, A., Antilla, J. C., Huang, X., & Buchwald, S. L. (2001) · Journal of the American Chemical Society · doi:10.1021/ja016226z · Cited by 1,021
Self-citationDriver, M. S., & Hartwig, J. F. (1997) · Journal of the American Chemical Society · doi:10.1021/ja971057x · Cited by 286
van Haaren, R. J., Goubitz, K., Fraanje, J., van Strijdonck, G. P. F., Oevering, H., Coussens, B. B., Reek, J. N. H., Kamer, P. C. J., & van Leeuwen, P. W. N. M. (2001) · Inorganic Chemistry · doi:10.1021/ic0009167 · Cited by 120
Cited by
Highly Efficient and Mild Copper‐Catalyzed N‐ and C‐Arylations with Aryl Bromides and Iodides
Cristau, H., Cellier, P. P., Spindler, J., & Taillefer, M. (2004) · Chemistry – A European Journal · doi:10.1002/chem.200400582 · Cited by 586
Bite angle effects of diphosphines in C–C and C–X bond forming cross coupling reactions
Birkholz (née Gensow), M.-N., Freixa, Z., & van Leeuwen, P. W. N. M. (2009) · Chemical Society Reviews · doi:10.1039/b806211k · Cited by 585
The Complementary Competitors: Palladium and Copper in C–N Cross-Coupling Reactions
Beletskaya, I. P., & Cheprakov, A. V. (2012) · Organometallics · doi:10.1021/om300683c · Cited by 454
Bite angle effects in diphosphine metal catalysts: steric or electronic?
Freixa, Z., & van Leeuwen, P. W. N. M. (2003) · Dalton Trans. · doi:10.1039/b300322c · Cited by 391
Primo, A., Liebel, M., & Quignard, F. (2009) · Chemistry of Materials · doi:10.1021/cm8020337 · Cited by 107
Metadata
- Authors
- Yin, J., & Buchwald, S. L.
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 2002-05-01
- Volume
- 124
- Issue
- 21
- Pages
- 6043-6048
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- OpenAlex
- W1972693920
- Cited by
- 469
- References
- 3
- FWCI
- 14.67
- Type
- journal article
- Language
- en
- Open access
- closed
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