Preparation of imides via the palladium-catalyzed coupling reaction of organoborons with methyl N -[methoxy(methylthio)methylene]carbamate as a one-carbon elongation reaction

Takuhei Tomizawa; Kohei Orimoto; Takashi Niwa; Masahisa Nakada

doi:10.1021/ol303062a

Preparation of imides via the palladium-catalyzed coupling reaction of organoborons with methyl N -[methoxy(methylthio)methylene]carbamate as a one-carbon elongation reaction

Takuhei Tomizawa, Kohei Orimoto, Takashi Niwa, Masahisa Nakada^*

^*Corresponding author for this work

School of Advanced Science and Engineering

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

19 Citations (Scopus)

Abstract

The preparation of imides via the palladium-catalyzed coupling reaction as a one-carbon elongation reaction is described. The palladium-catalyzed coupling reaction of aryl-, alkyl-, and alkenylborons with N-[methoxy(methylthio) methylene]carbamate in the presence of Cu(I) thiophene-2-carboxylate (CuTC) affords imino ethers that are converted to the corresponding imides by acidic hydrolysis in high yield. The imino ethers are also useful for preparing the corresponding ester without using carbon monoxide.

Original language	English
Pages (from-to)	6294-6297
Number of pages	4
Journal	Organic Letters
Volume	14
Issue number	24
DOIs	https://doi.org/10.1021/ol303062a
Publication status	Published - 2012 Dec 21

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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abstract = "The preparation of imides via the palladium-catalyzed coupling reaction as a one-carbon elongation reaction is described. The palladium-catalyzed coupling reaction of aryl-, alkyl-, and alkenylborons with N-[methoxy(methylthio) methylene]carbamate in the presence of Cu(I) thiophene-2-carboxylate (CuTC) affords imino ethers that are converted to the corresponding imides by acidic hydrolysis in high yield. The imino ethers are also useful for preparing the corresponding ester without using carbon monoxide.",

author = "Takuhei Tomizawa and Kohei Orimoto and Takashi Niwa and Masahisa Nakada",

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T1 - Preparation of imides via the palladium-catalyzed coupling reaction of organoborons with methyl N -[methoxy(methylthio)methylene]carbamate as a one-carbon elongation reaction

AU - Tomizawa, Takuhei

AU - Orimoto, Kohei

AU - Niwa, Takashi

AU - Nakada, Masahisa

PY - 2012/12/21

Y1 - 2012/12/21

N2 - The preparation of imides via the palladium-catalyzed coupling reaction as a one-carbon elongation reaction is described. The palladium-catalyzed coupling reaction of aryl-, alkyl-, and alkenylborons with N-[methoxy(methylthio) methylene]carbamate in the presence of Cu(I) thiophene-2-carboxylate (CuTC) affords imino ethers that are converted to the corresponding imides by acidic hydrolysis in high yield. The imino ethers are also useful for preparing the corresponding ester without using carbon monoxide.

AB - The preparation of imides via the palladium-catalyzed coupling reaction as a one-carbon elongation reaction is described. The palladium-catalyzed coupling reaction of aryl-, alkyl-, and alkenylborons with N-[methoxy(methylthio) methylene]carbamate in the presence of Cu(I) thiophene-2-carboxylate (CuTC) affords imino ethers that are converted to the corresponding imides by acidic hydrolysis in high yield. The imino ethers are also useful for preparing the corresponding ester without using carbon monoxide.

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JF - Organic Letters

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Preparation of imides via the palladium-catalyzed coupling reaction of organoborons with methyl N -[methoxy(methylthio)methylene]carbamate as a one-carbon elongation reaction

Abstract

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