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

6 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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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",

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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

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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