Palladium-catalyzed oxidative aminocarbonylation by decarboxylative coupling: Synthesis of alkynyl amides

Jinil Hwang; Jinseop Choi; Kyungho Park; Wonyoung Kim; Kwang Ho Song; Sunwoo Lee

doi:10.1002/ejoc.201403644

Palladium-catalyzed oxidative aminocarbonylation by decarboxylative coupling: Synthesis of alkynyl amides

Jinil Hwang, Jinseop Choi, Kyungho Park, Wonyoung Kim, Kwang Ho Song, Sunwoo Lee

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

31 Citations (Scopus)

Abstract

Alkynyl amides were synthesized from a palladium-catalyzed coupling reaction of alkynyl carboxylic acids and amines under carbon monoxide. The reaction was conducted with palladium(II) acetate (5 mol-%) and silver(I) oxide (1.0 equiv.) in acetonitrile at 80 °C for 1 h. This method provides good to moderate product yields and good functional group tolerance towards ketone, ester, and nitrile groups.

Original language	English
Pages (from-to)	2235-2243
Number of pages	9
Journal	European Journal of Organic Chemistry
Volume	2015
Issue number	10
DOIs	https://doi.org/10.1002/ejoc.201403644
Publication status	Published - 2015 Apr

Bibliographical note

Publisher Copyright:
Copyright © 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Keywords

Alkynes
Amides
Carbonylation
Palladium
Synthetic methods

ASJC Scopus subject areas

Physical and Theoretical Chemistry
Organic Chemistry

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10.1002/ejoc.201403644

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title = "Palladium-catalyzed oxidative aminocarbonylation by decarboxylative coupling: Synthesis of alkynyl amides",

abstract = "Alkynyl amides were synthesized from a palladium-catalyzed coupling reaction of alkynyl carboxylic acids and amines under carbon monoxide. The reaction was conducted with palladium(II) acetate (5 mol-%) and silver(I) oxide (1.0 equiv.) in acetonitrile at 80 °C for 1 h. This method provides good to moderate product yields and good functional group tolerance towards ketone, ester, and nitrile groups.",

keywords = "Alkynes, Amides, Carbonylation, Palladium, Synthetic methods",

author = "Jinil Hwang and Jinseop Choi and Kyungho Park and Wonyoung Kim and Song, {Kwang Ho} and Sunwoo Lee",

note = "Publisher Copyright: Copyright {\textcopyright} 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.",

year = "2015",

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doi = "10.1002/ejoc.201403644",

language = "English",

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T1 - Palladium-catalyzed oxidative aminocarbonylation by decarboxylative coupling

T2 - Synthesis of alkynyl amides

AU - Hwang, Jinil

AU - Choi, Jinseop

AU - Park, Kyungho

AU - Kim, Wonyoung

AU - Song, Kwang Ho

AU - Lee, Sunwoo

PY - 2015/4

Y1 - 2015/4

N2 - Alkynyl amides were synthesized from a palladium-catalyzed coupling reaction of alkynyl carboxylic acids and amines under carbon monoxide. The reaction was conducted with palladium(II) acetate (5 mol-%) and silver(I) oxide (1.0 equiv.) in acetonitrile at 80 °C for 1 h. This method provides good to moderate product yields and good functional group tolerance towards ketone, ester, and nitrile groups.

AB - Alkynyl amides were synthesized from a palladium-catalyzed coupling reaction of alkynyl carboxylic acids and amines under carbon monoxide. The reaction was conducted with palladium(II) acetate (5 mol-%) and silver(I) oxide (1.0 equiv.) in acetonitrile at 80 °C for 1 h. This method provides good to moderate product yields and good functional group tolerance towards ketone, ester, and nitrile groups.

KW - Alkynes

KW - Amides

KW - Carbonylation

KW - Palladium

KW - Synthetic methods

UR - http://www.scopus.com/inward/record.url?scp=84925632118&partnerID=8YFLogxK

U2 - 10.1002/ejoc.201403644

DO - 10.1002/ejoc.201403644

M3 - Article

AN - SCOPUS:84925632118

SN - 1434-193X

VL - 2015

SP - 2235

EP - 2243

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

IS - 10

ER -

Palladium-catalyzed oxidative aminocarbonylation by decarboxylative coupling: Synthesis of alkynyl amides

Abstract

Bibliographical note

Keywords

ASJC Scopus subject areas

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