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Synlett 2019; 30(07): 841-844
DOI: 10.1055/s-0037-1612414
DOI: 10.1055/s-0037-1612414
letter
Catalytic Carboxylation of Heteroaromatic Compounds: Double and Single Carboxylation with CO2
This work was financially supported by the Japan Society for the Promotion of Science (Grant-in-Aid for Scientific Research, No. 18K05096), the Naito Foundation, the Takeda Science Foundation, and the Sumitomo Foundation.Further Information
Publication History
Received: 05 February 2019
Accepted after revision: 19 February 2019
Publication Date:
19 March 2019 (online)
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.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1612414.
- Supporting Information
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