The DOI matches its Crossref record; 46 of the 46 references it cites were found in a registry or an index.
Visible Light-Mediated Direct Decarboxylative C–H Functionalization of Heteroarenes
Abstract
The direct visible light-mediated C–H alkylation of heteroarenes using aliphatic carboxylic acids is reported. This mild method proceeds at low catalyst loadings (0.5 mol %) and has a high functional group tolerance and a broad substrate scope. Notably, functionalization of (iso)quinoline, pyridine, phthalazine, benzothiazole, and other heterocyclic derivatives with both cyclic and acyclic primary, secondary, and tertiary carboxylic acids as well as amino and fatty acids proceeded under the standard conditions at room temperature. This protocol enables the rapid conversion of abundant feedstock materials into medically relevant “drug-like” moieties.
Overview
The claims and statistics of this paper haven’t been checked yet.
Run the check — free, no account needed. It reads the open-access text and checks the sources it cites.
Integrity signals
Registry
Cites
Statistics
Verification
Claims the paper makes
The claims and statistics of this paper haven’t been checked yet.
Run the check — free, no account needed. It reads the open-access text and checks the sources it cites.
Self-check
Percentages, sums and reported differences re-computed from the paper’s own numbers.
The self-check needs the paper’s full text.
Citations
Cites
Prier, C. K., Rankic, D. A., & MacMillan, D. W. C. (2013) · Chemical Reviews · doi:10.1021/cr300503r · Cited by 9,590
Visible light photoredox catalysis: applications in organic synthesis
Narayanam, J. M. R., & Stephenson, C. R. J. (2011) · Chem. Soc. Rev. · doi:10.1039/b913880n · Cited by 4,161
Visible light photocatalysis as a greener approach to photochemical synthesis
Yoon, T. P., Ischay, M. A., & Du, J. (2010) · Nature Chemistry · doi:10.1038/nchem.687 · Cited by 2,657
Solar Synthesis: Prospects in Visible Light Photocatalysis
Schultz, D. M., & Yoon, T. P. (2014) · Science · doi:10.1126/science.1239176 · Cited by 2,586
Visible‐Light Photoredox Catalysis
Xuan, J., & Xiao, W. (2012) · Angewandte Chemie International Edition · doi:10.1002/anie.201200223 · Cited by 2,262
Merging photoredox with nickel catalysis: Coupling of α-carboxyl sp 3 -carbons with aryl halides
Zuo, Z., Ahneman, D. T., Chu, L., Terrett, J. A., Doyle, A. G., & MacMillan, D. W. C. (2014) · Science · doi:10.1126/science.1255525 · Cited by 1,611
Trifluoromethylation of arenes and heteroarenes by means of photoredox catalysis
Nagib, D. A., & MacMillan, D. W. C. (2011) · Nature · doi:10.1038/nature10647 · Cited by 1,327
Shining Light on Photoredox Catalysis: Theory and Synthetic Applications
Tucker, J. W., & Stephenson, C. R. J. (2012) · The Journal of Organic Chemistry · doi:10.1021/jo202538x · Cited by 1,158
Characterizing chain processes in visible light photoredox catalysis
Cismesia, M. A., & Yoon, T. P. (2015) · Chemical Science · doi:10.1039/c5sc02185e · Cited by 1,067
Photoredox functionalization of C–H bonds adjacent to a nitrogen atom
Shi, L., & Xia, W. (2012) · Chemical Society Reviews · doi:10.1039/c2cs35203f · Cited by 1,062
Practical and innate carbon–hydrogen functionalization of heterocycles
Fujiwara, Y., Dixon, J. A., O’Hara, F., Funder, E. D., Dixon, D. D., Rodriguez, R. A., Baxter, R. D., Herlé, B., Sach, N., Collins, M. R., et al. (2012) · Nature · doi:10.1038/nature11680 · Cited by 924
Visible‐Light‐Induced Decarboxylative Functionalization of Carboxylic Acids and Their Derivatives
Xuan, J., Zhang, Z., & Xiao, W. (2015) · Angewandte Chemie International Edition · doi:10.1002/anie.201505731 · Cited by 826
Alcohols as alkylating agents in heteroarene C–H functionalization
Jin, J., & MacMillan, D. W. C. (2015) · Nature · doi:10.1038/nature14885 · Cited by 737
Hopkinson, M. N., Sahoo, B., Li, J., & Glorius, F. (2014) · Chemistry – A European Journal · doi:10.1002/chem.201304823 · Cited by 700
Self-citationZuo, Z., & MacMillan, D. W. C. (2014) · Journal of the American Chemical Society · doi:10.1021/ja501621q · Cited by 570
Late‐Stage Functionalization of Biologically Active Heterocycles Through Photoredox Catalysis
DiRocco, D. A., Dykstra, K., Krska, S., Vachal, P., Conway, D. V., & Tudge, M. (2014) · Angewandte Chemie International Edition · doi:10.1002/anie.201402023 · Cited by 488
Nucleophilic character of alkyl radicals—VI
Minisci, F., Bernardi, R., Bertini, F., Galli, R., & Perchinummo, M. (1971) · Tetrahedron · doi:10.1016/s0040-4020(01)97768-3 · Cited by 484
Controlled Fluoroalkylation Reactions by Visible-Light Photoredox Catalysis
Chatterjee, T., Iqbal, N., You, Y., & Cho, E. J. (2016) · Accounts of Chemical Research · doi:10.1021/acs.accounts.6b00248 · Cited by 467
Jin, J., & MacMillan, D. W. C. (2015) · Angewandte Chemie International Edition · doi:10.1002/anie.201410432 · Cited by 456
Recent Developments of Free-Radical Substitutions of Heteroaromatic Bases
Minisci, F., Vismara, E., & Fontana, F. (1989) · HETEROCYCLES · doi:10.3987/rev-88-sr1 · Cited by 452
Liu, J., Liu, Q., Yi, H., Qin, C., Bai, R., Qi, X., Lan, Y., & Lei, A. (2014) · Angewandte Chemie International Edition · doi:10.1002/anie.201308614 · Cited by 451
Noble, A., McCarver, S. J., & MacMillan, D. W. C. (2015) · Journal of the American Chemical Society · doi:10.1021/ja511913h · Cited by 448
Photoredox α-Vinylation of α-Amino Acids and N-Aryl Amines
Noble, A., & MacMillan, D. W. C. (2014) · Journal of the American Chemical Society · doi:10.1021/ja506094d · Cited by 431
A scalable and operationally simple radical trifluoromethylation
Beatty, J. W., Douglas, J. J., Cole, K. P., & Stephenson, C. R. J. (2015) · Nature Communications · doi:10.1038/ncomms8919 · Cited by 401
Decarboxylative Fluorination of Aliphatic Carboxylic Acids via Photoredox Catalysis
Ventre, S., Petronijevic, F. R., & MacMillan, D. W. C. (2015) · Journal of the American Chemical Society · doi:10.1021/jacs.5b02244 · Cited by 390
Li, G.-X., Morales-Rivera, C. A., Wang, Y., Gao, F., He, G., Liu, P., & Chen, G. (2016) · Chemical Science · doi:10.1039/c6sc02653b · Cited by 330
Griffin, J. D., Zeller, M. A., & Nicewicz, D. A. (2015) · Journal of the American Chemical Society · doi:10.1021/jacs.5b07770 · Cited by 327
Zhou, Q., Guo, W., Ding, W., Wu, X., Chen, X., Lu, L., & Xiao, W. (2015) · Angewandte Chemie International Edition · doi:10.1002/anie.201504559 · Cited by 326
Direct Alkylation of Heteroaryls Using Potassium Alkyl- and Alkoxymethyltrifluoroborates
Molander, G. A., Colombel, V., & Braz, V. A. (2011) · Organic Letters · doi:10.1021/ol2003572 · Cited by 288
Matsui, J. K., Primer, D. N., & Molander, G. A. (2017) · Chemical Science · doi:10.1039/c7sc00283a · Cited by 284
Beatty, J. W., Douglas, J. J., Miller, R. D., McAtee, R. C., Cole, K. P., & Stephenson, C. R. J. (2016) · Chem · doi:10.1016/j.chempr.2016.08.002 · Cited by 277
Cheng, W.-M., Shang, R., & Fu, Y. (2017) · ACS Catalysis · doi:10.1021/acscatal.6b03215 · Cited by 263
Direct C–F Bond Formation Using Photoredox Catalysis
Rueda-Becerril, M., Mahé, O., Drouin, M., Majewski, M. B., West, J. G., Wolf, M. O., Sammis, G. M., & Paquin, J.-F. (2014) · Journal of the American Chemical Society · doi:10.1021/ja412083f · Cited by 261
Lexicon of lipid nutrition (IUPAC Technical Report)
Beare-Rogers, J. L., Dieffenbacher, A., & Holm, J. V. (2001) · Pure and Applied Chemistry · doi:10.1351/pac200173040685 · Cited by 260
Temperature dependence of the rate constants for reactions of the sulfate radical, SO4-, with anions
Huie, R. E., & Clifton, C. L. (1990) · The Journal of Physical Chemistry · doi:10.1021/j100386a015 · Cited by 242
Electron spin resonance and pulse radiolysis studies of some reactions of peroxysulfate (SO4.1,2)
Chawla, O. P., & Fessenden, R. W. (1975) · The Journal of Physical Chemistry · doi:10.1021/j100591a020 · Cited by 241
Le Vaillant, F., Courant, T., & Waser, J. (2015) · Angewandte Chemie International Edition · doi:10.1002/anie.201505111 · Cited by 224
Friedel–Crafts Amidoalkylation via Thermolysis and Oxidative Photocatalysis
Dai, C., Meschini, F., Narayanam, J. M. R., & Stephenson, C. R. J. (2012) · The Journal of Organic Chemistry · doi:10.1021/jo300162c · Cited by 212
Direct alkylation of heteroarenes with unactivated bromoalkanes using photoredox gold catalysis
McCallum, T., & Barriault, L. (2016) · Chemical Science · doi:10.1039/c6sc00807k · Cited by 208
Photoredox‐Catalysed Decarboxylative Alkylation of N‐Heteroarenes with N‐(Acyloxy)phthalimides
Cheng, W., Shang, R., Fu, M., & Fu, Y. (2017) · Chemistry – A European Journal · doi:10.1002/chem.201605640 · Cited by 200
Tlahuext‐Aca, A., Garza‐Sanchez, R. A., & Glorius, F. (2017) · Angewandte Chemie International Edition · doi:10.1002/anie.201700049 · Cited by 193
Self-citationCassani, C., Bergonzini, G., & Wallentin, C.-J. (2014) · Organic Letters · doi:10.1021/ol5019294 · Cited by 176
Simple Sulfinate Synthesis Enables CH Trifluoromethylcyclopropanation
Gianatassio, R., Kawamura, S., Eprile, C. L., Foo, K., Ge, J., Burns, A. C., Collins, M. R., & Baran, P. S. (2014) · Angewandte Chemie International Edition · doi:10.1002/anie.201406622 · Cited by 167
Photoredox-Catalyzed Hydroxymethylation of Heteroaromatic Bases
Huff, C. A., Cohen, R. D., Dykstra, K. D., Streckfuss, E. C., DiRocco, D. A., & Krska, S. W. (2016) · The Journal of Organic Chemistry · doi:10.1021/acs.joc.6b00811 · Cited by 143
Yoshimi, Y., Masuda, M., Mizunashi, T., Nishikawa, K., Maeda, K., Koshida, N., Itou, T., Morita, T., & Hatanaka, M. (2009) · Organic Letters · doi:10.1021/ol9019277 · Cited by 113
Rustgi, S. N., & Riesz, P. (1978) · International Journal of Radiation Biology and Related Studies in Physics Chemistry and Medicine · doi:10.1080/09553007814550941 · Cited by 41
Cited by
Photoredox-Catalyzed C–H Functionalization Reactions
Holmberg-Douglas, N., & Nicewicz, D. A. (2022) · Chemical Reviews · doi:10.1021/acs.chemrev.1c00311 · Cited by 989
Photocatalytic Late-Stage C–H Functionalization
Bellotti, P., Huang, H.-M., Faber, T., & Glorius, F. (2023) · Chemical Reviews · doi:10.1021/acs.chemrev.2c00478 · Cited by 623
Self-citationCatalytic enantioselective Minisci-type addition to heteroarenes
Proctor, R. S. J., Davis, H. J., & Phipps, R. J. (2018) · Science · doi:10.1126/science.aar6376 · Cited by 527
Tay, N. E. S., Lehnherr, D., & Rovis, T. (2022) · Chemical Reviews · doi:10.1021/acs.chemrev.1c00384 · Cited by 518
Photoelectrochemical C−H Alkylation of Heteroarenes with Organotrifluoroborates
Yan, H., Hou, Z., & Xu, H. (2019) · Angewandte Chemie International Edition · doi:10.1002/anie.201814488 · Cited by 283
Metadata
- Authors
- Garza-Sanchez, R. A., Tlahuext-Aca, A., Tavakoli, G., & Glorius, F.
- Venue
- ACS Catalysis
- Publisher
- American Chemical Society (ACS)
- Published
- 2017-05-16
- Volume
- 7
- Issue
- 6
- Pages
- 4057-4061
- ISSN
- 2155-5435 (ISSN-L)
- OpenAlex
- W2613453516
- Cited by
- 285
- References
- 46
- FWCI
- 14.93
- Type
- journal article
- Language
- en
- Open access
- closed
About these checks
Registry, retraction, Cites and statistics results are computed, not judged, with one exception: a printed reference that no index lists is read once by a model before it counts as a citation error. Claims are extracted by a model and kept only when their quote appears verbatim in the text; each cited source is then checked, with a model’s help, for whether it says what the claim relies on. Those verdicts can be wrong — read the claim’s quote and the cited source before relying on one.
Statistics and arithmetic are recomputed, not judged.
Confidence bands are shown only for fields calibrated on our annotated test set. None is calibrated yet, so no band is shown.
What counts as a claim ›How we measure confidence ›How we check this ›
Are you an author, or do you see a problem with this page? Request a review
Data sources
Bibliographic data: Semantic Scholar, OpenAlex, Crossref.
Contains information from the Semantic Scholar Academic Graph Datasets, made available under the ODC Attribution License (ODC-BY 1.0).
Semantic Scholar’s data is described in: Kinney, R., et al. (2023). The Semantic Scholar Open Data Platform. arXiv:2301.10140.