Catalytic Carboxylation of Heteroaromatic Compounds: Double and Single Carboxylation with CO2

Tsuyoshi Mita; Hiroki Masutani; Sho Ishii; Yoshihiro Sato

doi:10.1055/s-0037-1612414

Synlett, Table of Contents

Synlett 2019; 30(07): 841-844
DOI: 10.1055/s-0037-1612414

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Catalytic Carboxylation of Heteroaromatic Compounds: Double and Single Carboxylation with CO₂

Tsuyoshi Mita *

Faculty of Pharmaceutical Sciences, Hokkaido University, Sapporo 060-0812, Japan Email: tmita@pharm.hokudai.ac.jp Email: biyo@pharm.hokudai.ac.jp

,

Hiroki Masutani

,

Sho Ishii

,

Yoshihiro Sato *

Faculty of Pharmaceutical Sciences, Hokkaido University, Sapporo 060-0812, Japan Email: tmita@pharm.hokudai.ac.jp Email: biyo@pharm.hokudai.ac.jp

› Author Affiliations

Abstract

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Abstract

In the presence of PdCl₂[P(n-Bu)₃]₂ (10 mol%) and ZnEt₂, 2-furyl and 2-pyrrolylmethyl acetate were carboxylated with CO₂ (1 atm), affording doubly carboxylated products in good yields. In this dearomative transformation, α,ε-dicarboxylic acids were obtained selectively, in contrast to our previous report in which α,γ-dicarboxylic acids were selectively produced from 2-indolylmethyl acetates. In contrast, 5-thiazolylmethyl acetate and naphthylmethyl acetates predominantly underwent single carboxylation.

Key words

carboxylation - CO₂ - dearomatization - palladium - furan - pyrrole

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References

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