New lithium-zincate approaches for the selective functionalisation of pyrazine: direct dideprotozincation vs. nucleophilic alkylation
Abstract
Comparing the reactivity of the related lithium zincates [(THF)LiZn(TMP)(t)Bu(2)] (1) and [(PMDETA)LiZn(t)Bu(3)] (2) towards pyrazine discloses two new bimetallic approaches for the selective 2,5-dideprotonation and room temperature C-H alkylation of this sensitive heterocycle.
Integrity signals
Registry
Cites
Statistics
Claims the paper makes
Claims other papers make about this one
Each is checked against this paper’s own text: does it say what the citing paper says it does?
SPEs can last from several hours to several weeks.
“SPEs can last from several hours to several weeks [29], [30], [31].”
From Hindlimb suspension and spe-like radiation impairs clearance of bacterial infections (2014) · cites this paper as [31]
Cites
Metalated Heterocycles and Their Applications in Synthetic Organic Chemistry
Chinchílla, R., Nájera, C., & Yus, M. (2004) · Chemical Reviews · doi:10.1021/cr020101a · Cited by 349 · see citing works
Avant-Garde Metalating Agents: Structural Basis of Alkali-Metal-Mediated Metalation
Mulvey, R. E. (2009) · Accounts of Chemical Research · doi:10.1021/ar800254y · Cited by 347 · see citing works
TMP−Zincate as Highly Chemoselective Base for Directed Ortho Metalation
Kondo, Y., Shilai, M., Uchiyama, M., et al. (1999) · Journal of the American Chemical Society · doi:10.1021/ja984263t · Cited by 309 · see citing works
Tobisu, M., Hyodo, I., & Chatani, N. (2009) · Journal of the American Chemical Society · doi:10.1021/ja9053509 · Cited by 286 · see citing works
Quéguiner, G., Marsais, F., Snieckus, V. A., et al. (1991) · Advances in heterocyclic chemistry · doi:10.1016/s0065-2725(08)60965-4 · Cited by 218 · see citing works
Deprotonative Metalation of Five-Membered Aromatic Heterocycles Using Mixed Lithium−Zinc Species
L'Helgoual'c, J.-M., Seggio, A., Chevallier, F., et al. (2007) · The Journal of Organic Chemistry · doi:10.1021/jo7020345 · Cited by 152 · see citing works
Synergic Sedation of Sensitive Anions: Alkali-Mediated Zincation of Cyclic Ethers and Ethene
Kennedy, A. R., Klett, J., Mulvey, R. E., et al. (2009) · Science · doi:10.1126/science.1178165 · Cited by 148 · see citing works
Self-citationLithium-Mediated Zincation of Pyrazine, Pyridazine, Pyrimidine, and Quinoxaline
Seggio, A., Chevallier, F., Vaultier, M., et al. (2007) · The Journal of Organic Chemistry · doi:10.1021/jo0708341 · Cited by 111 · see citing works
Functionalization of diazines and benzo derivatives through deprotonated intermediates
Chevallier, F., & Mongin, F. (2007) · Chemical Society Reviews · doi:10.1039/b709416g · Cited by 104 · see citing works
Split Personality of Lithium Chloride: Recent Salt Effects in Organometallic Recipes
Hevia, E., & Mulvey, R. E. (2011) · Angewandte Chemie International Edition · doi:10.1002/anie.201102054 · Cited by 102 · see citing works
Self-citationPlé, N., Turck, A., Couture, K., et al. (1995) · The Journal of Organic Chemistry · doi:10.1021/jo00117a033 · Cited by 95 · see citing works
Dong, Z., Clososki, G. C., Wunderlich, S. H., et al. (2008) · Chemistry - A European Journal · doi:10.1002/chem.200801558 · Cited by 90 · see citing works
Clegg, W., Conway, B., Hevia, E., et al. (2009) · Journal of the American Chemical Society · doi:10.1021/ja8087168 · Cited by 88 · see citing works
Self-citationHunter, H. N., Hadei, N., Blagojevic, V., et al. (2011) · Chemistry - A European Journal · doi:10.1002/chem.201101029 · Cited by 72 · see citing works
Mulvey, R. E., Dunbar, L., Clegg, W., et al. (1996) · Angewandte Chemie International Edition in English · doi:10.1002/anie.199607531 · Cited by 53 · see citing works
Armstrong, D. R., Blair, V. L., Clegg, W., Dale, S. H., García‐Álvarez, J., Honeyman, G. W., Hevia, E., Mulvey, R. E., & Russo, L. (2010) · Journal of the American Chemical Society · doi:10.1021/ja1038598 · Cited by 49 · see citing works
Self-citationBlair, V. L., Blakemore, D. C., Hay, D. A., et al. (2011) · Tetrahedron Letters · doi:10.1016/j.tetlet.2011.06.090 · Cited by 42 · see citing works
Self-citationNobuto, D., & Uchiyama, M. (2008) · The Journal of Organic Chemistry · doi:10.1021/jo701895z · Cited by 39 · see citing works
Unprecedented C-6 functionalisation of 3-picoline induced by a methyl to C-6 lithium shift
Mathieu, J., Gros, P. C., & Fort, Y. (2000) · Chemical Communications · doi:10.1039/b001690j · Cited by 34 · see citing works
Flagged first, then by citations
Cited by
Sorted by citations
Hindlimb suspension and spe-like radiation impairs clearance of bacterial infections
Li, M., Holmes, V., Zhou, Y., Ni, H., Sanzari, J. K., Kennedy, A. R., & Weissman, D. (2014) · PLoS ONE · doi:10.1371/journal.pone.0085665 · Cited by 43 · see citing works
Self-citation
- Authors
- Baillie, S. E., Blair, V. L., Blakemore, D. C., Hay, D., Kennedy, A. R., Pryde, D. C., & Hevia, E.
- Affiliations
- University of Strathclyde (GB)
- Pfizer (United Kingdom) (GB)
- Corresponding author
- Hevia, Eva
- Venue
- Chemical Communications
- Publisher
- Royal Society of Chemistry (RSC)
- Published
- 2012
- Volume
- 48
- Issue
- 14
- Pages
- 1985
- ISSN
- 1359-7345 (ISSN-L)
- 1364-548X
- OpenAlex
- W2035236985
- Cited by
- 50
- References
- 19
- Citations by year
- 2026: 2 · 2025: 2 · 2024: 1 · 2023: 3 · 2022: 4 · 2020: 1 · 2019: 2 · 2018: 3 · 2017: 2 · 2016: 5 · 2015: 7 · 2014: 2 · 2013: 12 · 2012: 4
- FWCI
- 2.71
- Type
- journal article
- Language
- en
- Open access
- closed
- Locations
- Chemical Communications (publishedVersion)
- PubMed (publishedVersion)
- Funders
- Engineering and Physical Sciences Research Council (EP/E036244/1, EP/H034528/1)
- Topics
- Physical Sciences › Chemistry › Organic Chemistry › Coordination Chemistry and Organometallics
- Physical Sciences › Chemistry › Organic Chemistry › Inorganic and Organometallic Chemistry
- Physical Sciences › Chemistry › Inorganic Chemistry › Synthesis and characterization of novel inorganic/organometallic compounds
- Keywords
- pyrazine, C–H alkylation, nucleophilic alkylation
- MeSH terms
- Alkylation, Heterocyclic Compounds, Lithium, Molecular Conformation, Magnetic Resonance Spectroscopy, Protons, Pyrazines, Temperature, Zirconium
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
