N-heterocyclic olefins as robust organocatalyst for the chemical conversion of carbon dioxide to value-added chemicals

Vitthal B. Saptal; Bhalchandra M. Bhanage

doi:10.1002/cssc.201600467

N-heterocyclic olefins as robust organocatalyst for the chemical conversion of carbon dioxide to value-added chemicals

Vitthal B. Saptal, Bhalchandra M. Bhanage^*

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

117 Scopus citations

Abstract

In this report, the activity of N-heterocyclic olefins (NHOs) as a newly emerging class of organocatalyst is investigated for the chemical fixation of carbon dioxide through reactions with aziridines to form oxazolidinones and the N-formylation of amines with polymethylhydrosiloxane (PMHS) or 9-borabicy-clo[3.3.1]nonane (9-BBN) as the reducing agent under mild conditions. The exocyclic carbon atoms of NHOs are highly nucleophilic owing to the electron-donating ability of the two nitrogen atoms. This high nucleophilicity of the NHOs activates CO₂ molecules to form zwitterionic NHO–carboxylate (NHO– CO₂) adducts, which are active in formylation reactions as well as the carboxylation of aziridines to oxazolidinones.

Original language	English
Pages (from-to)	1980-1985
Number of pages	6
Journal	ChemSusChem
Volume	9
Issue number	15
DOIs	https://doi.org/10.1002/cssc.201600467
State	Published - 9 Aug 2016
Externally published	Yes

Keywords

Carbon dioxide fixation
Cycloaddition
Nitrogen heterocycles
Organocatalysis
Zwitterions

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10.1002/cssc.201600467

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title = "N-heterocyclic olefins as robust organocatalyst for the chemical conversion of carbon dioxide to value-added chemicals",

abstract = "In this report, the activity of N-heterocyclic olefins (NHOs) as a newly emerging class of organocatalyst is investigated for the chemical fixation of carbon dioxide through reactions with aziridines to form oxazolidinones and the N-formylation of amines with polymethylhydrosiloxane (PMHS) or 9-borabicy-clo[3.3.1]nonane (9-BBN) as the reducing agent under mild conditions. The exocyclic carbon atoms of NHOs are highly nucleophilic owing to the electron-donating ability of the two nitrogen atoms. This high nucleophilicity of the NHOs activates CO2 molecules to form zwitterionic NHO–carboxylate (NHO– CO2) adducts, which are active in formylation reactions as well as the carboxylation of aziridines to oxazolidinones.",

keywords = "Carbon dioxide fixation, Cycloaddition, Nitrogen heterocycles, Organocatalysis, Zwitterions",

author = "Saptal, {Vitthal B.} and Bhanage, {Bhalchandra M.}",

note = "Publisher Copyright: {\textcopyright} 2016 Wiley-VCH Verlag GmbH &Co. KGaA, Weinheim.",

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doi = "10.1002/cssc.201600467",

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AU - Bhanage, Bhalchandra M.

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N2 - In this report, the activity of N-heterocyclic olefins (NHOs) as a newly emerging class of organocatalyst is investigated for the chemical fixation of carbon dioxide through reactions with aziridines to form oxazolidinones and the N-formylation of amines with polymethylhydrosiloxane (PMHS) or 9-borabicy-clo[3.3.1]nonane (9-BBN) as the reducing agent under mild conditions. The exocyclic carbon atoms of NHOs are highly nucleophilic owing to the electron-donating ability of the two nitrogen atoms. This high nucleophilicity of the NHOs activates CO2 molecules to form zwitterionic NHO–carboxylate (NHO– CO2) adducts, which are active in formylation reactions as well as the carboxylation of aziridines to oxazolidinones.

AB - In this report, the activity of N-heterocyclic olefins (NHOs) as a newly emerging class of organocatalyst is investigated for the chemical fixation of carbon dioxide through reactions with aziridines to form oxazolidinones and the N-formylation of amines with polymethylhydrosiloxane (PMHS) or 9-borabicy-clo[3.3.1]nonane (9-BBN) as the reducing agent under mild conditions. The exocyclic carbon atoms of NHOs are highly nucleophilic owing to the electron-donating ability of the two nitrogen atoms. This high nucleophilicity of the NHOs activates CO2 molecules to form zwitterionic NHO–carboxylate (NHO– CO2) adducts, which are active in formylation reactions as well as the carboxylation of aziridines to oxazolidinones.

KW - Carbon dioxide fixation

KW - Cycloaddition

KW - Nitrogen heterocycles

KW - Organocatalysis

KW - Zwitterions

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SN - 1864-5631

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SP - 1980

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JO - ChemSusChem

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IS - 15

ER -

N-heterocyclic olefins as robust organocatalyst for the chemical conversion of carbon dioxide to value-added chemicals

Abstract

Keywords

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