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Carbon Dioxide as the C1 Source for Direct C−H Functionalization of Aromatic Heterocycles

https://doi.org/10.1021/ol101450u
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35/35 checkable references clean · checked 2026-07-23

Every reference with a DOI in the deposited reference list resolved to a known work in Crossref or DataCite at the dated check, and none carried a retraction, withdrawal, or removal notice.

4 without a DOI — not checked. A reference deposited without a DOI is never matched by title or guessed at; it stays outside the checked set, and this line discloses that.

The 35 checked references that resolve
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Reactions of carbon dioxide with carbon-carbon bond formation catalyzed by transition-metal complexes
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Carbon Dioxide as an Alternative C<sub>1</sub> Synthetic Unit: Activation by Transition‐Metal Complexes
resolves10.1039/b700658f
Utilisation of CO2 as a chemical feedstock: opportunities and challenges
resolves10.2174/1385272053765033
Transition Metal Catalyzed Reactions of Carbon Dioxide and Other Heterocumulenes
resolves10.1039/b411802b
Bidentate amidine ligands for nickel(0)-mediated coupling of carbon dioxide with unsaturated hydrocarbons
resolves10.1021/jo982443f
Nickel-Mediated Regio- and Chemoselective Carboxylation of Alkynes in the Presence of Carbon Dioxide
resolves10.1021/ja026620c
Novel Catalytic CO<sub>2</sub> Incorporation Reaction:  Nickel-Catalyzed Regio- and Stereoselective Ring-Closing Carboxylation of Bis-1,3-dienes
resolves10.1002/anie.200900667
Metal‐Catalyzed Carboxylation of Organometallic Reagents with Carbon Dioxide
resolves10.1021/ja9639832
Palladium-Catalyzed Carboxylation of Allyl Stannanes
resolves10.1002/anie.200801857
Carboxylation of Organoboronic Esters Catalyzed by N‐Heterocyclic Carbene Copper(I) Complexes
resolves10.1021/ol800829q
Copper(I)-Catalyzed Carboxylation of Aryl- and Alkenylboronic Esters
resolves10.1021/ja061232m
Rhodium(I)-Catalyzed Carboxylation of Aryl- and Alkenylboronic Esters with CO<sub>2</sub>
resolves10.1021/ja803435w
Beyond Aresta’s Complex: Ni- and Pd-Catalyzed Organozinc Coupling with CO<sub>2</sub>
resolves10.1021/ol800764u
Nickel-Catalyzed Carboxylation of Organozinc Reagents with CO<sub>2</sub>
resolves10.1002/anie.201000634
MgCl<sub>2</sub>‐Accelerated Addition of Functionalized Organozinc Reagents to Aldehydes, Ketones, and Carbon Dioxide
resolves10.1021/ja806677w
Hydrocarboxylation of Allenes with CO<sub>2</sub> Catalyzed by Silyl Pincer-Type Palladium Complex
resolves10.1021/ja8062925
Nickel-Catalyzed Reductive Carboxylation of Styrenes Using CO<sub>2</sub>
resolves10.1021/ja905264a
Palladium-Catalyzed Direct Carboxylation of Aryl Bromides with Carbon Dioxide
resolves10.1021/ja020787o
Efficient Chemoselective Carboxylation of Aromatics to Arylcarboxylic Acids with a Superelectrophilically Activated Carbon Dioxide−Al<sub>2</sub>Cl<sub>6</sub>/Al System
resolves10.1002/anie.200907040
The Nickel/Copper‐Catalyzed Direct Alkylation of Heterocyclic CH Bonds
resolves10.1021/ar9000058
Palladium- and Copper-Catalyzed Arylation of Carbon−Hydrogen Bonds
resolves10.1021/ja805688p
A General Method for Copper-Catalyzed Arylation of Arene C−H Bonds
resolves10.1002/anie.200906996
Nickel‐Catalyzed Direct CH Arylation and Alkenylation of Heteroarenes with Organosilicon Reagents
resolves10.1002/chem.200902916
Copper‐Mediated Direct Cross‐Coupling of 1,3,4‐Oxadiazoles and Oxazoles with Terminal Alkynes
resolves10.1021/ol9001587
Nickel-Catalyzed Biaryl Coupling of Heteroarenes and Aryl Halides/Triflates
resolves10.1002/anie.200702141
Direct Arylation of Thiazoles on Water
resolves10.1002/anie.200804517
Palladium‐Catalyzed Direct Arylations of Heteroarenes with Tosylates and Mesylates
resolves10.1002/anie.200904776
Copper as a Powerful Catalyst in the Direct Alkynylation of Azoles
resolves10.1002/anie.200900413
Copper‐Catalyzed Direct C Arylation of Heterocycles with Aryl Bromides: Discovery of Fluorescent Core Frameworks
resolves10.1021/ja100354j
A Highly Efficient Palladium/Copper Cocatalytic System for Direct Arylation of Heteroarenes: An Unexpected Effect of Cu(Xantphos)I
resolves10.1002/anie.201001470
Nickel‐Catalyzed Hydroheteroarylation of Vinylarenes
resolves10.1021/ja101939r
A New Entry of Amination Reagents for Heteroaromatic C−H Bonds: Copper-Catalyzed Direct Amination of Azoles with Chloroamines at Room Temperature
resolves10.1002/(SICI)1521-3897(199902)341:2<186::AID-PRAC186>3.0.CO;2-6
Cesium carbonate: A powerful inorganic base in organic synthesis
resolves10.1021/ja103429q
Carboxylation of C−H Bonds Using <i>N</i>-Heterocyclic Carbene Gold(I) Complexes
The 4 references without a DOI — listed, not checked
no DOI — not checkedref17/cit17
no DOI — not checkedBordwell pKatable, available athttp://www.chem.wisc.edu/areas/reich/pkatable/index.htm.
no DOI — not checkedSix of the seven commercial Cs2CO3tested mediated the carboxylation and gave reproducible results. The six sources are Aldrich (98% and 99.995%), Acros (99.5%), Alfa Aesar (99%), VWR (extra pure), and Chem-Impex (99.9%). Only the Cs2CO3from Alfa Aesar (99.994%) did not work. Control experiment showed that it is likely due to the fact that this Cs2CO3contains ca. 1 equiv of water, which inhibits the reaction. SeeSupporting Informationfor details.
no DOI — not checkedSeeSupporting Information.
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