Carboxylation of indoles and pyrroles with CO2 in the presence of dialkylaluminum halides

Nemoto, Koji; Onozawa, Satoru; Egusa, Naoki; Morohashi, Naoya; Hattori, Tetsutaro

doi:10.1016/j.tetlet.2009.05.076

Cited by 53 publications

(19 citation statements)

References 27 publications

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“…30 atm) by using dialkylaluminum halides (Me 2 AlCl) instead of aluminum trihalides. [29] This method is applicable to the regioselective carboxylationo f1 -methylindoles, 1-benzylpyrroles, and1 -phenylpyrroles to afford the corresponding indole-3-carboxylic acids and pyrrole-2-carboxylic acids in good yields (Scheme 17). Unprotected simple indole or pyrrole could also undergo carboxylation but low yields resulted.…”

Section: Lewis-acid-mediated Carboxylationmentioning

confidence: 99%

C−H Carboxylation of Aromatic Compounds through CO₂ Fixation

2017

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Carbon dioxide (CO2) represents the most abundant and accessible carbon source on Earth. Thus the ability to transform CO2 into valuable commodity chemicals through the construction of C−C bonds is an invaluable strategy. Carboxylic acids and derivatives, the main products obtained by carboxylation of carbon nucleophiles by reaction of CO2, have wide application in pharmaceuticals and advanced materials. Among the variety of carboxylation methods currently available, the direct carboxylation of C−H bonds with CO2 has attracted much attention owing to advantages from a step‐ and atom‐economical point of view. In particular, the prevalence of (hetero)aromatic carboxylic acids and derivatives among biologically active compounds has led to significant interest in the development of methods for their direct carboxylation from CO2. Herein, the latest achievements in the area of direct C−H carboxylation of (hetero)aromatic compounds with CO2 will be discussed.

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Section: Lewis-acid-mediated Carboxylationmentioning

confidence: 99%

C−H Carboxylation of Aromatic Compounds through CO₂ Fixation

2017

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“…[5] More recently,K obayashi and co-workers developed the carboxylation of different indole derivatives,mediated by an excess of tBuOLi. [5] More recently,K obayashi and co-workers developed the carboxylation of different indole derivatives,mediated by an excess of tBuOLi.…”

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confidence: 99%

Organocatalyzed CO₂ Trapping Using Alkynyl Indoles

et al. 2015

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The first organocatalyzed trapping of CO2 through C-C and C-O bond formation is reported. Alkynyl indoles together with catalytic amounts of an organic base and five equivalents of CO2 resulted in the formation new heterocyclic structures. These tricyclic indole-containing products were successfully prepared under mild reaction conditions from aromatic, heteroaromatic, and aliphatic alkynyl indoles with complete regioselectivity. Further investigations suggest that C-C bond formation is the initial intermolecular step, followed by lactone-forming C-O bond formation.

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“…Other modifi cation of such Friedel-Craft s type carboxylation systems were reported consequently, [82][83][84] including AlBr 3 for naphthalene derivatives, AlBr 3 /R 3 SiCl for fused carbocycles, and Me 2 AlCl for heterocycles. Th e aluminium reagents used in this study are all stoichiometric.…”

Section: Reaction Of Aromatic C(sp 2 )-H With Comentioning

confidence: 99%

Catalytic conversion of carbon dioxide to carboxylic acid derivatives

Liu

2014

Greenhouse Gases

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Chemical utilization of the greenhouse gas, i.e., CO 2 as an abundant, easily available, and renewable carbon feedstock for producing chemicals, materials, and fuels is attractive as an integral part of the carbon cycle. Based on the principle of CO 2 activation and elaborately designed catalysts, various transformation of CO 2 can be realized under mild conditions. In particular, establishing practical methodologies for catalytic carboxylation by CO 2 as carboxylative reagent would be a fascinating dream for synthetic chemists. This review covers the updated advances in the catalytic conversion of CO 2 into carboxylic acid derivatives from alkenes, alkynes, aromatic halides, aromatic C(sp 2 )-H bonds, etc.

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Carboxylation of indoles and pyrroles with CO2 in the presence of dialkylaluminum halides

Cited by 53 publications

References 27 publications

C−H Carboxylation of Aromatic Compounds through CO₂ Fixation

C−H Carboxylation of Aromatic Compounds through CO₂ Fixation

Organocatalyzed CO₂ Trapping Using Alkynyl Indoles

Catalytic conversion of carbon dioxide to carboxylic acid derivatives

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Carboxylation of indoles and pyrroles with CO2 in the presence of dialkylaluminum halides

Cited by 53 publications

References 27 publications

C−H Carboxylation of Aromatic Compounds through CO2 Fixation

C−H Carboxylation of Aromatic Compounds through CO2 Fixation

Organocatalyzed CO2 Trapping Using Alkynyl Indoles

Catalytic conversion of carbon dioxide to carboxylic acid derivatives

Contact Info

Product

Resources

About

C−H Carboxylation of Aromatic Compounds through CO₂ Fixation

C−H Carboxylation of Aromatic Compounds through CO₂ Fixation

Organocatalyzed CO₂ Trapping Using Alkynyl Indoles