Highly Efficient Synthesis of Alkyl N-Arylcarbamates from CO2, Anilines, and Branched Alcohols with a Catalyst System of CeO2 and 2-Cyanopyridine

Yu Gu; Ayaka Miura; Masazumi Tamura; Yoshinao Nakagawa; Keiichi Tomishige

doi:10.1021/acssuschemeng.9b04318

Highly Efficient Synthesis of Alkyl N-Arylcarbamates from CO₂, Anilines, and Branched Alcohols with a Catalyst System of CeO₂ and 2-Cyanopyridine

Yu Gu, Ayaka Miura, Masazumi Tamura, Yoshinao Nakagawa, Keiichi Tomishige

ENG - Applied Chemistry

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

22 Citations (Scopus)

Abstract

Highly efficient synthesis of alkyl N-arylcarbamates from CO₂, anilines, and alcohols using the CeO₂ and 2-cyanopyridine catalyst system was substantiated by selecting branched alcohols, such as 2-propanol and cyclohexanol, with minimized formation of byproducts, such as dialkyl carbonates and picolinamide. The catalyst system is operable even at low CO₂ pressure (≤1 MPa), and the target carbamates were obtained with high arylamine-based yields (up to 94%).

Original language	English
Pages (from-to)	16795-16802
Number of pages	8
Journal	ACS Sustainable Chemistry and Engineering
Volume	7
Issue number	19
DOIs	https://doi.org/10.1021/acssuschemeng.9b04318
Publication status	Published - 2019 Oct 7

Keywords

arylamine
carbamate
carbon dioxide
cerium oxide
heterogeneous catalyst

ASJC Scopus subject areas

Chemistry(all)
Environmental Chemistry
Chemical Engineering(all)
Renewable Energy, Sustainability and the Environment

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

Access to Document

10.1021/acssuschemeng.9b04318

Cite this

@article{e5d7a16ce9954709a1f8d6bd73370d68,

title = "Highly Efficient Synthesis of Alkyl N-Arylcarbamates from CO2, Anilines, and Branched Alcohols with a Catalyst System of CeO2 and 2-Cyanopyridine",

abstract = "Highly efficient synthesis of alkyl N-arylcarbamates from CO2, anilines, and alcohols using the CeO2 and 2-cyanopyridine catalyst system was substantiated by selecting branched alcohols, such as 2-propanol and cyclohexanol, with minimized formation of byproducts, such as dialkyl carbonates and picolinamide. The catalyst system is operable even at low CO2 pressure (≤1 MPa), and the target carbamates were obtained with high arylamine-based yields (up to 94%).",

keywords = "arylamine, carbamate, carbon dioxide, cerium oxide, heterogeneous catalyst",

author = "Yu Gu and Ayaka Miura and Masazumi Tamura and Yoshinao Nakagawa and Keiichi Tomishige",

note = "Funding Information: This work was supported by JST PRESTO grant number JPMJPR15S5 and JSPS KAKENHI grant number 18H05247. Publisher Copyright: Copyright {\textcopyright} 2019 American Chemical Society.",

year = "2019",

month = oct,

day = "7",

doi = "10.1021/acssuschemeng.9b04318",

language = "English",

volume = "7",

pages = "16795--16802",

journal = "ACS Sustainable Chemistry and Engineering",

issn = "2168-0485",

publisher = "American Chemical Society",

number = "19",

}

TY - JOUR

T1 - Highly Efficient Synthesis of Alkyl N-Arylcarbamates from CO2, Anilines, and Branched Alcohols with a Catalyst System of CeO2 and 2-Cyanopyridine

AU - Gu, Yu

AU - Miura, Ayaka

AU - Tamura, Masazumi

AU - Nakagawa, Yoshinao

AU - Tomishige, Keiichi

PY - 2019/10/7

Y1 - 2019/10/7

N2 - Highly efficient synthesis of alkyl N-arylcarbamates from CO2, anilines, and alcohols using the CeO2 and 2-cyanopyridine catalyst system was substantiated by selecting branched alcohols, such as 2-propanol and cyclohexanol, with minimized formation of byproducts, such as dialkyl carbonates and picolinamide. The catalyst system is operable even at low CO2 pressure (≤1 MPa), and the target carbamates were obtained with high arylamine-based yields (up to 94%).

AB - Highly efficient synthesis of alkyl N-arylcarbamates from CO2, anilines, and alcohols using the CeO2 and 2-cyanopyridine catalyst system was substantiated by selecting branched alcohols, such as 2-propanol and cyclohexanol, with minimized formation of byproducts, such as dialkyl carbonates and picolinamide. The catalyst system is operable even at low CO2 pressure (≤1 MPa), and the target carbamates were obtained with high arylamine-based yields (up to 94%).

KW - arylamine

KW - carbamate

KW - carbon dioxide

KW - cerium oxide

KW - heterogeneous catalyst

UR - http://www.scopus.com/inward/record.url?scp=85073101974&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85073101974&partnerID=8YFLogxK

U2 - 10.1021/acssuschemeng.9b04318

DO - 10.1021/acssuschemeng.9b04318

M3 - Article

AN - SCOPUS:85073101974

VL - 7

SP - 16795

EP - 16802

JO - ACS Sustainable Chemistry and Engineering

JF - ACS Sustainable Chemistry and Engineering

SN - 2168-0485

IS - 19

ER -