The DOI matches its Crossref record; 15 of the 15 references it cites were found in a registry or an index.
Synthetic and Mechanistic Studies of Pd-Catalyzed C−H Arylation with Diaryliodonium Salts: Evidence for a Bimetallic High Oxidation State Pd Intermediate
Open accessAbstract
This contribution describes the substrate scope and mechanism of Pd-catalyzed ligand-directed C-H arylation with diaryliodonium salts. This transformation was applied to the synthesis of a variety of different biaryl products, using directing groups including pyridines, quinolines, pyrrolidinones, and oxazolidinones. Electronically and sterically diverse aryl groups (Ar) were transferred in high yield using iodine(III) reagents of general structure [Mes-I-Ar]BF(4). Mechanistic investigations have been conducted that establish the kinetic order of the catalytic reaction in each component, determine the resting state of the catalyst and the iodine(III) reagent, quantify the electronic influence of the arylating reagent on the reaction rate, and establish the intra- and intermolecular 1 degree H/D kinetic isotope effect. On the basis of these studies, this transformation is proposed to proceed via turnover-limiting oxidation of the Pd dimer [Pd(N~C)(OAc)](2) (N~C = 3-methyl-2-phenylpyridine) by [Mes-I-Ph]BF(4). This mechanism implicates a bimetallic high oxidation state Pd species as a key catalytic intermediate. The significance of this and other aspects of the proposed mechanism are discussed in detail.
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Cites
Palladium-Catalyzed Cross-Coupling Reactions of Organoboron Compounds
Miyaura, N., & Suzuki, A. (1995) · Chemical Reviews · doi:10.1021/cr00039a007 · Cited by 12,817
The Heck Reaction as a Sharpening Stone of Palladium Catalysis
Beletskaya, I. P., & Cheprakov, A. V. (2000) · Chemical Reviews · doi:10.1021/cr9903048 · Cited by 3,902
Aryl−Aryl Bond Formation by Transition-Metal-Catalyzed Direct Arylation
Alberico, D., Scott, M. E., & Lautens, M. (2007) · Chemical Reviews · doi:10.1021/cr0509760 · Cited by 3,640
Stille, J. K. (1986) · Angewandte Chemie International Edition in English · doi:10.1002/anie.198605081 · Cited by 3,394
Suzuki, A. (1999) · Journal of Organometallic Chemistry · doi:10.1016/s0022-328x(98)01055-9 · Cited by 2,916
C-H Bond Functionalization in Complex Organic Synthesis
Godula, K., & Sames, D. (2006) · Science · doi:10.1126/science.1114731 · Cited by 2,161
C−C, C−O, C−N Bond Formation on sp2 Carbon by Pd(II)-Catalyzed Reactions Involving Oxidant Agents
Beccalli, E. M., Broggini, G., Martinelli, M., & Sottocornola, S. (2007) · Chemical Reviews · doi:10.1021/cr068006f · Cited by 1,196
Determination of Association Constants (Ka) from Solution NMR Data
Fielding, L. (2000) · Tetrahedron · doi:10.1016/s0040-4020(00)00492-0 · Cited by 839
Oxidative C−H Activation/C−C Bond Forming Reactions: Synthetic Scope and Mechanistic Insights
Kalyani, D., Deprez, N. R., Desai, L. V., & Sanford, M. S. (2005) · Journal of the American Chemical Society · doi:10.1021/ja051402f · Cited by 796
Self-citationPalladium-Catalyzed Methylation and Arylation of sp2 and sp3 C−H Bonds in Simple Carboxylic Acids
Giri, R., Maugel, N., Li, J.-J., Wang, D.-H., Breazzano, S. P., Saunders, L. B., & Yu, J.-Q. (2007) · Journal of the American Chemical Society · doi:10.1021/ja0701614 · Cited by 777
Cited by
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Metallaphotoredox: The Merger of Photoredox and Transition Metal Catalysis
Chan, A. Y., Perry, I. B., Bissonnette, N. B., Buksh, B. F., Edwards, G. A., Frye, L. I., Garry, O. L., Lavagnino, M. N., Li, B. X., Liang, Y., et al. (2022) · Chemical Reviews · doi:10.1021/acs.chemrev.1c00383 · Cited by 1,754
Controlling Site Selectivity in Palladium-Catalyzed C–H Bond Functionalization
Neufeldt, S. R., & Sanford, M. S. (2012) · Accounts of Chemical Research · doi:10.1021/ar300014f · Cited by 1,360
Self-citationKalyani, D., McMurtrey, K. B., Neufeldt, S. R., & Sanford, M. S. (2011) · Journal of the American Chemical Society · doi:10.1021/ja208068w · Cited by 676
Self-citationC–H Functionalization in the Synthesis of Amino Acids and Peptides
Noisier, A. F. M., & Brimble, M. A. (2014) · Chemical Reviews · doi:10.1021/cr500200x · Cited by 600
Metadata
- Authors
- Deprez, N. R., & Sanford, M. S.
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 2009-07-21
- Volume
- 131
- Issue
- 31
- Pages
- 11234-11241
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- OpenAlex
- W2027303432
- Cited by
- 522
- References
- 15
- FWCI
- 25.06
- Type
- journal article
- Language
- en
- Open access
- green
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- Deprez, N. R., & Sanford, M. S. (2009). Synthetic and Mechanistic Studies of Pd-Catalyzed C−H Arylation with Diaryliodonium Salts: Evidence for a Bimetallic High Oxidation State Pd Intermediate. Journal of the American Chemical Society. https://doi.org/10.1021/ja904116k
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