Direct Carboxylation of Electron-Rich Heteroarenes Promoted by LiO-tBu with CsF and [18]Crown-6

Masanori Shigeno; Kazuya Hanasaka; Keita Sasaki; Kanako Nozawa-Kumada; Yoshinori Kondo

doi:10.1002/chem.201805926

Direct Carboxylation of Electron-Rich Heteroarenes Promoted by LiO-tBu with CsF and [18]Crown-6

Masanori Shigeno, Kazuya Hanasaka, Keita Sasaki, Kanako Nozawa-Kumada, Yoshinori Kondo

PHA - Molecular Pharmaceutical Science

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

13 Citations (Scopus)

Abstract

We herein demonstrate that the combination of LiO-tBu, CsF, and [18]crown-6 efficiently promotes the direct C−H carboxylation of electron-rich heteroarenes (benzothiophene, thiophene, benzofuran, and furan derivatives). A variety of functional groups, including methyl, methoxy, halo, cyano, amide, and keto moieties, are compatible with this system. The reaction proceeds via the formation of a tert-butyl carbonate species.

Original language	English
Pages (from-to)	3235-3239
Number of pages	5
Journal	Chemistry - A European Journal
Volume	25
Issue number	13
DOIs	https://doi.org/10.1002/chem.201805926
Publication status	Published - 2019 Mar 1

Keywords

Brønsted base
C−H functionalization
carbon dioxide
carboxylation
heterocycles

ASJC Scopus subject areas

Catalysis
Organic Chemistry

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10.1002/chem.201805926

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title = "Direct Carboxylation of Electron-Rich Heteroarenes Promoted by LiO-tBu with CsF and [18]Crown-6",

abstract = "We herein demonstrate that the combination of LiO-tBu, CsF, and [18]crown-6 efficiently promotes the direct C−H carboxylation of electron-rich heteroarenes (benzothiophene, thiophene, benzofuran, and furan derivatives). A variety of functional groups, including methyl, methoxy, halo, cyano, amide, and keto moieties, are compatible with this system. The reaction proceeds via the formation of a tert-butyl carbonate species.",

keywords = "Br{\o}nsted base, C−H functionalization, carbon dioxide, carboxylation, heterocycles",

author = "Masanori Shigeno and Kazuya Hanasaka and Keita Sasaki and Kanako Nozawa-Kumada and Yoshinori Kondo",

note = "Funding Information: This work was financially supported by JSPS KAKENHI Grant Number 16H00997 in Precisely Designed Catalysts with Customized Scaffolding (Y.K.), JSPS KAKENHI Grant Number 17K15419 (M.S.), Grand for Basic Science Research Projects from The Sumitomo Foundation (M.S.), Yamaguchi Educational and Scholarship Foundation (M.S.), and also the Platform Project for Supporting Drug Discovery and Life Science Research funded by Japan Agency for Medical Research and Development (AMED) (M.S., K.N.K., and Y.K.). Publisher Copyright: {\textcopyright} 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim",

year = "2019",

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doi = "10.1002/chem.201805926",

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T1 - Direct Carboxylation of Electron-Rich Heteroarenes Promoted by LiO-tBu with CsF and [18]Crown-6

AU - Shigeno, Masanori

AU - Hanasaka, Kazuya

AU - Sasaki, Keita

AU - Nozawa-Kumada, Kanako

AU - Kondo, Yoshinori

N1 - Funding Information: This work was financially supported by JSPS KAKENHI Grant Number 16H00997 in Precisely Designed Catalysts with Customized Scaffolding (Y.K.), JSPS KAKENHI Grant Number 17K15419 (M.S.), Grand for Basic Science Research Projects from The Sumitomo Foundation (M.S.), Yamaguchi Educational and Scholarship Foundation (M.S.), and also the Platform Project for Supporting Drug Discovery and Life Science Research funded by Japan Agency for Medical Research and Development (AMED) (M.S., K.N.K., and Y.K.). Publisher Copyright: © 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

PY - 2019/3/1

Y1 - 2019/3/1

N2 - We herein demonstrate that the combination of LiO-tBu, CsF, and [18]crown-6 efficiently promotes the direct C−H carboxylation of electron-rich heteroarenes (benzothiophene, thiophene, benzofuran, and furan derivatives). A variety of functional groups, including methyl, methoxy, halo, cyano, amide, and keto moieties, are compatible with this system. The reaction proceeds via the formation of a tert-butyl carbonate species.

AB - We herein demonstrate that the combination of LiO-tBu, CsF, and [18]crown-6 efficiently promotes the direct C−H carboxylation of electron-rich heteroarenes (benzothiophene, thiophene, benzofuran, and furan derivatives). A variety of functional groups, including methyl, methoxy, halo, cyano, amide, and keto moieties, are compatible with this system. The reaction proceeds via the formation of a tert-butyl carbonate species.

KW - Brønsted base

KW - C−H functionalization

KW - carbon dioxide

KW - carboxylation

KW - heterocycles

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JO - Chemistry - A European Journal

JF - Chemistry - A European Journal

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ER -

Direct Carboxylation of Electron-Rich Heteroarenes Promoted by LiO-tBu with CsF and [18]Crown-6

Abstract

Keywords

ASJC Scopus subject areas

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