The DOI matches its Crossref record; 14 of the 14 references it cites were found in a registry or an index.
Selective Iron-Catalyzed Cross-Coupling Reactions of Grignard Reagents with Enol Triflates, Acid Chlorides, and Dichloroarenes
Abstract
Cheap, readily available, air stable, nontoxic, and environmentally benign iron salts such as Fe(acac)(3) are excellent precatalysts for the cross-coupling of Grignard reagents with alkenyl triflates and acid chlorides. Moreover, it is shown that dichloroarene and -heteroarene derivatives as the substrates can be selectively monoalkylated by this method. All cross-coupling reactions proceed very rapidly under notably mild conditions and turned out to be compatible with a variety of functional groups in both reaction partners. A detailed analysis of the preparative results suggests that iron-catalyzed C-C bond formations can occur via different pathways. Thus, it is likely that reactions of methylmagnesium halides involve iron-ate complexes as the active components, whereas reactions of Grignard reagents with two or more carbon atoms are effected by highly reduced iron-clusters of the formal composition [Fe(MgX)(2)](n) generated in situ. Control experiments using the ate-complex [Me(4)Fe]Li(2) corroborate this interpretation.
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
Comprehensive organic synthesis
Knochel, P., & Molander, G. A. (2014) · Elsevier eBooks · Cited by 6,231
Suzuki, A. (1999) · Journal of Organometallic Chemistry · doi:10.1016/s0022-328x(98)01055-9 · Cited by 2,916
Iron-Catalyzed Cross-Coupling Reactions
Fürstner, A., Leitner, A., Méndez, M., & Krause, H. (2002) · Journal of the American Chemical Society · doi:10.1021/ja027190t · Cited by 823
Self-citationVinylation of Grignard reagents. Catalysis by iron
Tamura, M., & Kochi, J. K. (1971) · Journal of the American Chemical Society · doi:10.1021/ja00735a030 · Cited by 603
Coupling of Grignard Reagents with Organic Halides
Tamura, M., & Kochi, J. K. (1971) · Synthesis · doi:10.1055/s-1971-35043 · Cited by 489
Fürstner, A., & Leitner, A. (2002) · Angewandte Chemie International Edition · doi:10.1002/1521-3773(20020215)41:4<609::aid-anie609>3.0.co;2-m · Cited by 432
Self-citationHighly Stereo- and Chemoselective Iron-Catalyzed Alkenylation of Organomagnesium Compounds
Cahiez, G., & Avedissian, H. (1998) · Synthesis · doi:10.1055/s-1998-2135 · Cited by 380
Iron-Catalyzed Grignard Cross-Coupling with Alkyl Halides Possessing β-Hydrogens
Nagano, T., & Hayashi, T. (2004) · Organic Letters · doi:10.1021/ol049779y · Cited by 295
Neumann, S. M., & Kochi, J. K. (1975) · The Journal of Organic Chemistry · doi:10.1021/jo00893a013 · Cited by 249
Mechanistic studies of iron catalysis in the cross coupling of alkenyl halides and Grignard reagents
Smith, R. S., & Kochi, J. K. (1976) · The Journal of Organic Chemistry · doi:10.1021/jo00865a019 · Cited by 240
Cited by
The Promise and Challenge of Iron-Catalyzed Cross Coupling
Sherry, B. D., & Fürstner, A. (2008) · Accounts of Chemical Research · doi:10.1021/ar800039x · Cited by 1,235
Self-citationFürstner, A. (2016) · ACS Central Science · doi:10.1021/acscentsci.6b00272 · Cited by 746
Self-citationAdvances in Iron Catalyzed Cross Coupling Reactions
Fürstner, A., & Martin, R. (2005) · Chemistry Letters · doi:10.1246/cl.2005.624 · Cited by 472
Self-citationCross‐Coupling of Alkyl Halides with Aryl Grignard Reagents Catalyzed by a Low‐Valent Iron Complex
Martin, R., & Fürstner, A. (2004) · Angewandte Chemie International Edition · doi:10.1002/anie.200460504 · Cited by 400
Self-citationIron‐Catalyzed Cross‐Couplings in the Synthesis of Pharmaceuticals: In Pursuit of Sustainability
Piontek, A., Bisz, E., & Szostak, M. (2018) · Angewandte Chemie International Edition · doi:10.1002/anie.201800364 · Cited by 285
Metadata
- Authors
- Scheiper, B., Bonnekessel, M., Krause, H., & Fürstner, A.
- Venue
- The Journal of Organic Chemistry
- Publisher
- American Chemical Society (ACS)
- Published
- 2004-05-01
- Volume
- 69
- Issue
- 11
- Pages
- 3943-3949
- ISSN
- 0022-3263 (ISSN-L)
- 1520-6904
- OpenAlex
- W2127041713
- Cited by
- 339
- References
- 14
- FWCI
- 13.35
- 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
How to cite
Cite CoChat for the checks on this page, and the paper for its own findings.
- This page
- CoChat. (2026). Citation check: Selective Iron-Catalyzed Cross-Coupling Reactions of Grignard Reagents with Enol Triflates, Acid Chlorides, and Dichloroarenes. https://app.cochat.ai/papers/10.1021/jo0498866
- The paper
- Scheiper, B., Bonnekessel, M., Krause, H., & Fürstner, A. (2004). Selective Iron-Catalyzed Cross-Coupling Reactions of Grignard Reagents with Enol Triflates, Acid Chlorides, and Dichloroarenes. The Journal of Organic Chemistry. https://doi.org/10.1021/jo0498866
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.
