The DOI matches its Crossref record; 19 of the 19 references it cites were found in a registry or an index.
Generation of Phosphoranyl Radicals via Photoredox Catalysis Enables Voltage–Independent Activation of Strong C–O Bonds
Open accessAbstract
Despite the prevalence of alcohols and carboxylic acids as functional groups in organic molecules and the potential to serve as radical precursors, C-O bonds remain difficult to activate. We report a synthetic strategy for direct access to both alkyl and acyl radicals from these ubiquitous functional groups via photoredox catalysis. This method exploits the unique reactivity of phosphoranyl radicals, generated from a polar/SET crossover between a phosphine radical cation and an oxygen-centered nucleophile. We show the desired reactivity in the reduction of benzylic alcohols to the corresponding benzyl radicals with terminal H atom trapping to afford the deoxygenated products. Using the same method, we demonstrate access to synthetically versatile acyl radicals, which enables the reduction of aromatic and aliphatic carboxylic acids to the corresponding aldehydes with exceptional chemoselectivity. This protocol also transforms carboxylic acids to heterocycles and cyclic ketones via intramolecular acyl radical cyclizations to forge C-O, C-N, and C-C bonds in a single step.
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
Photoredox Catalysis in Organic Chemistry
Shaw, M. H., Twilton, J., & MacMillan, D. W. C. (2016) · The Journal of Organic Chemistry · doi:10.1021/acs.joc.6b01449 · Cited by 3,186
Single-electron transmetalation in organoboron cross-coupling by photoredox/nickel dual catalysis
Tellis, J. C., Primer, D. N., & Molander, G. A. (2014) · Science · doi:10.1126/science.1253647 · Cited by 1,281
Chatgilialoglu, C., Crich, D., Komatsu, M., & Ryu, I. (1999) · Chemical Reviews · doi:10.1021/cr9601425 · Cited by 898
Nicewicz, D., Roth, H., & Romero, N. (2015) · Synlett · doi:10.1055/s-0035-1561297 · Cited by 763
Free Radical Chemistry Enabled by Visible Light-Induced Electron Transfer
Staveness, D., Bosque, I., & Stephenson, C. R. J. (2016) · Accounts of Chemical Research · doi:10.1021/acs.accounts.6b00270 · Cited by 610
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
Nawrat, C. C., Jamison, C. R., Slutskyy, Y., MacMillan, D. W. C., & Overman, L. E. (2015) · Journal of the American Chemical Society · doi:10.1021/jacs.5b07678 · Cited by 403
Chu, L., Lipshultz, J. M., & MacMillan, D. W. C. (2015) · Angewandte Chemie International Edition · doi:10.1002/anie.201501908 · Cited by 333
A general deoxygenation approach for synthesis of ketones from aromatic carboxylic acids and alkenes
Zhang, M., Xie, J., & Zhu, C. (2018) · Nature Communications · doi:10.1038/s41467-018-06019-1 · Cited by 330
Cited by
Kwon, K., Simons, R. T., Nandakumar, M., & Roizen, J. L. (2022) · Chemical Reviews · doi:10.1021/acs.chemrev.1c00444 · Cited by 389
Lipshultz, J. M., Li, G., & Radosevich, A. T. (2021) · Journal of the American Chemical Society · doi:10.1021/jacs.0c12816 · Cited by 353
Metadata
- Authors
- Stache, E. E., Ertel, A. B., Rovis, T., & Doyle, A. G.
- Venue
- ACS Catalysis
- Publisher
- American Chemical Society (ACS)
- Published
- 2018-10-18
- Volume
- 8
- Issue
- 12
- Pages
- 11134-11139
- ISSN
- 2155-5435 (ISSN-L)
- OpenAlex
- W2897878623
- Cited by
- 366
- References
- 19
- FWCI
- 10.94
- Type
- journal article
- Language
- en
- Open access
- green
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
How to cite
Cite CoChat for the checks on this page, and the paper for its own findings.
- This page
- CoChat. (2026). Citation check: Generation of Phosphoranyl Radicals via Photoredox Catalysis Enables Voltage–Independent Activation of Strong C–O Bonds. https://app.cochat.ai/papers/10.1021/acscatal.8b03592
- The paper
- Stache, E. E., Ertel, A. B., Rovis, T., & Doyle, A. G. (2018). Generation of Phosphoranyl Radicals via Photoredox Catalysis Enables Voltage–Independent Activation of Strong C–O Bonds. ACS Catalysis. https://doi.org/10.1021/acscatal.8b03592
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.
