The DOI matches its Crossref record; 22 of the 22 references it cites were found in a registry or an index.
N-Heterocyclic Carbene-Catalyzed Decarboxylative Alkylation of Aldehydes
Abstract
We found that N-heterocyclic carbene catalysis promoted the unprecedented decarboxylative coupling of aryl aldehydes and tertiary or secondary alkyl carboxylic acid-derived redox-active esters to produce aryl alkyl ketones. The mild and transition-metal-free reaction conditions are attractive features of this method. The power of this protocol was demonstrated by the functionalization of pharmaceutical drugs and natural product. A reaction pathway involving single electron transfer from an enolate form of Breslow intermediate to a redox ester followed by recombination of the resultant radical pair to form a carbon-carbon bond is proposed.
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Cites
An overview of N-heterocyclic carbenes
Hopkinson, M. N., Richter, C., Schedler, M., & Glorius, F. (2014) · Nature · doi:10.1038/nature13384 · Cited by 4,264
Organocatalytic Reactions Enabled by N-Heterocyclic Carbenes
Flanigan, D. M., Romanov-Michailidis, F., White, N. A., & Rovis, T. (2015) · Chemical Reviews · doi:10.1021/acs.chemrev.5b00060 · Cited by 2,045
N-Heterocyclic Carbene Catalysis via the α,β-Unsaturated Acyl Azolium
Zhang, C., Hooper, J. F., & Lupton, D. W. (2017) · ACS Catalysis · doi:10.1021/acscatal.6b03663 · Cited by 480
Okada, K., Okamoto, K., Morita, N., Okubo, K., & Oda, M. (1991) · Journal of the American Chemical Society · doi:10.1021/ja00024a074 · Cited by 446
Biomimetic Carbene‐Catalyzed Oxidations of Aldehydes Using TEMPO
Guin, J., De Sarkar, S., Grimme, S., & Studer, A. (2008) · Angewandte Chemie International Edition · doi:10.1002/anie.200802735 · Cited by 421
Thiamin Diphosphate Catalysis: Enzymic and Nonenzymic Covalent Intermediates
Kluger, R., & Tittmann, K. (2008) · Chemical Reviews · doi:10.1021/cr068444m · Cited by 281
Pyruvate Ferredoxin Oxidoreductase and Its Radical Intermediate
Ragsdale, S. W. (2003) · Chemical Reviews · doi:10.1021/cr020423e · Cited by 259
White, N. A., & Rovis, T. (2014) · Journal of the American Chemical Society · doi:10.1021/ja5080739 · Cited by 217
Zhang, Y., Du, Y., Huang, Z., Xu, J., Wu, X., Wang, Y., Wang, M., Yang, S., Webster, R. D., & Chi, Y. R. (2015) · Journal of the American Chemical Society · doi:10.1021/ja511371a · Cited by 195
Tlahuext‐Aca, A., Garza‐Sanchez, R. A., & Glorius, F. (2017) · Angewandte Chemie International Edition · doi:10.1002/anie.201700049 · Cited by 193
Piel, I., Pawelczyk, M. D., Hirano, K., Fröhlich, R., & Glorius, F. (2011) · European Journal of Organic Chemistry · doi:10.1002/ejoc.201100870 · Cited by 166
Crystal Structure of the Free Radical Intermediate of Pyruvate:Ferredoxin Oxidoreductase
Chabrière, E., Vernède, X., Guigliarelli, B., Charon, M.-H., Hatchikian, E. C., & Fontecilla-Camps, J. C. (2001) · Science · doi:10.1126/science.1066198 · Cited by 165
Chen, X.-Y., Chen, K.-Q., Sun, D.-Q., & Ye, S. (2017) · Chemical Science · doi:10.1039/c6sc04135c · Cited by 159
N‐Heterocyclic Carbene Catalyzed γ‐Dihalomethylenation of Enals by Single‐Electron Transfer
Yang, W., Hu, W., Dong, X., Li, X., & Sun, J. (2016) · Angewandte Chemie International Edition · doi:10.1002/anie.201608371 · Cited by 142
Introduction to Enzyme and Coenzyme Chemistry
Bugg, T. (2004) · Wiley eBooks · doi:10.1002/9781444305364 · Cited by 132
Wu, X., Zhang, Y., Wang, Y., Ke, J., Jeret, M., Reddi, R. N., Yang, S., Song, B., & Chi, Y. R. (2017) · Angewandte Chemie International Edition · doi:10.1002/anie.201611692 · Cited by 109
Du, Y., Wang, Y., Li, X., Shao, Y., Li, G., Webster, R. D., & Chi, Y. R. (2014) · Organic Letters · doi:10.1021/ol5027415 · Cited by 96
Li, B., Wang, Y., Proctor, R. S. J., Zhang, Y., Webster, R. D., Yang, S., Song, B., & Chi, Y. R. (2016) · Nature Communications · doi:10.1038/ncomms12933 · Cited by 94
Mansoorabadi, S. O., Seravalli, J., Furdui, C. M., Krymov, V., Gerfen, G. J., Begley, T. P., Melnick, J. S., Ragsdale, S. W., & Reed, G. H. (2006) · Biochemistry · doi:10.1021/bi0602516 · Cited by 76
Zhao, K., & Enders, D. (2017) · Angewandte Chemie International Edition · doi:10.1002/anie.201700370 · Cited by 63
Electron transfer properties of active aldehydes derived from thiamin coenzyme analogues
Nakanishi, I., & Itoh, S. (1997) · Chemical Communications · doi:10.1039/a704559j · Cited by 51
Wang, Y., Du, Y., Huang, X., Wu, X., Zhang, Y., Yang, S., & Chi, Y. R. (2017) · Organic Letters · doi:10.1021/acs.orglett.6b03792 · Cited by 39
Cited by
Recent advances in N-heterocyclic carbene-based radical catalysis
Ishii, T., Nagao, K., & Ohmiya, H. (2020) · Chemical Science · doi:10.1039/d0sc01538e · Cited by 394
Self-citationLiu, K., Schwenzer, M., & Studer, A. (2022) · ACS Catalysis · doi:10.1021/acscatal.2c03996 · Cited by 325
Metadata
- Authors
- Ishii, T., Kakeno, Y., Nagao, K., & Ohmiya, H.
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 2019-02-20
- Volume
- 141
- Issue
- 9
- Pages
- 3854-3858
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- OpenAlex
- W2915743380
- Cited by
- 336
- References
- 22
- FWCI
- 15.03
- Type
- journal article
- Language
- en
- Open access
- closed
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