Palladium(II)-Catalysed Aminocarbonylation of Terminal Alkynes for the Synthesis of 2-Ynamides: Addressing the Challenges of Solvents and Gas Mixtures

Nicola Hughes; Clare L Brown; Andrew A Irwin; Qun Cao; Mark J Muldoon

doi:10.1002/cssc.201601601

Palladium(II)-Catalysed Aminocarbonylation of Terminal Alkynes for the Synthesis of 2-Ynamides: Addressing the Challenges of Solvents and Gas Mixtures

Nicola Hughes, Clare L Brown, Andrew A Irwin, Qun Cao, Mark J Muldoon

Research output: Contribution to journal › Article

9 Citations (Scopus)

193 Downloads (Pure)

Abstract

2-Ynamides can be synthesised through Pd(II) catalysed oxidative carbonylation, utilising low catalyst loadings. A variety of alkynes and amines can be used to afford 2-ynamides in high yields, whilst overcoming the drawbacks associated with previous oxidative methods, which rely on dangerous solvents and gas mixtures. The use of [NBu4 ]I allows the utilisation of the industrially recommended solvent ethyl acetate. O2 can be used as the terminal oxidant, and the catalyst can operate under safer conditions with low O2 concentrations.

Original language	English
Pages (from-to)	675-680
Number of pages	6
Journal	CHEMSUSCHEM
Volume	10
Issue number	4
Early online date	23 Jan 2017
DOIs	https://doi.org/10.1002/cssc.201601601
Publication status	Early online date - 23 Jan 2017

Keywords

Journal Article

Access to Document

10.1002/cssc.201601601Licence: CC BY

Palladium(II)-Catalysed Aminocarbonylation of Terminal Alkynes for the Synthesis of 2-Ynamides: Addressing the Challenges of Solvents and Gas Mixtures
Copyright The Authors 2017. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the Creative Commons Attribution License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.
Final published version, 794 KBLicence: CC BY

Fingerprint Dive into the research topics of 'Palladium(II)-Catalysed Aminocarbonylation of Terminal Alkynes for the Synthesis of 2-Ynamides: Addressing the Challenges of Solvents and Gas Mixtures'. Together they form a unique fingerprint.

Cite this

Hughes, N., Brown, C. L., Irwin, A. A., Cao, Q., & Muldoon, M. J. (2017). Palladium(II)-Catalysed Aminocarbonylation of Terminal Alkynes for the Synthesis of 2-Ynamides: Addressing the Challenges of Solvents and Gas Mixtures. CHEMSUSCHEM, 10(4), 675-680. https://doi.org/10.1002/cssc.201601601

@article{93da106d2080463f904c41c8c05a2bc1,

title = "Palladium(II)-Catalysed Aminocarbonylation of Terminal Alkynes for the Synthesis of 2-Ynamides: Addressing the Challenges of Solvents and Gas Mixtures",

abstract = "2-Ynamides can be synthesised through Pd(II) catalysed oxidative carbonylation, utilising low catalyst loadings. A variety of alkynes and amines can be used to afford 2-ynamides in high yields, whilst overcoming the drawbacks associated with previous oxidative methods, which rely on dangerous solvents and gas mixtures. The use of [NBu4 ]I allows the utilisation of the industrially recommended solvent ethyl acetate. O2 can be used as the terminal oxidant, and the catalyst can operate under safer conditions with low O2 concentrations.",

keywords = "Journal Article",

author = "Nicola Hughes and Brown, {Clare L} and Irwin, {Andrew A} and Qun Cao and Muldoon, {Mark J}",

note = "{\textcopyright} 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.",

year = "2017",

month = jan,

day = "23",

doi = "10.1002/cssc.201601601",

language = "English",

volume = "10",

pages = "675--680",

journal = "CHEMSUSCHEM",

issn = "1864-5631",

publisher = "Wiley-VCH Verlag",

number = "4",

}

TY - JOUR

T1 - Palladium(II)-Catalysed Aminocarbonylation of Terminal Alkynes for the Synthesis of 2-Ynamides: Addressing the Challenges of Solvents and Gas Mixtures

AU - Hughes, Nicola

AU - Brown, Clare L

AU - Irwin, Andrew A

AU - Cao, Qun

AU - Muldoon, Mark J

PY - 2017/1/23

Y1 - 2017/1/23

N2 - 2-Ynamides can be synthesised through Pd(II) catalysed oxidative carbonylation, utilising low catalyst loadings. A variety of alkynes and amines can be used to afford 2-ynamides in high yields, whilst overcoming the drawbacks associated with previous oxidative methods, which rely on dangerous solvents and gas mixtures. The use of [NBu4 ]I allows the utilisation of the industrially recommended solvent ethyl acetate. O2 can be used as the terminal oxidant, and the catalyst can operate under safer conditions with low O2 concentrations.

AB - 2-Ynamides can be synthesised through Pd(II) catalysed oxidative carbonylation, utilising low catalyst loadings. A variety of alkynes and amines can be used to afford 2-ynamides in high yields, whilst overcoming the drawbacks associated with previous oxidative methods, which rely on dangerous solvents and gas mixtures. The use of [NBu4 ]I allows the utilisation of the industrially recommended solvent ethyl acetate. O2 can be used as the terminal oxidant, and the catalyst can operate under safer conditions with low O2 concentrations.

KW - Journal Article

U2 - 10.1002/cssc.201601601

DO - 10.1002/cssc.201601601

M3 - Article

C2 - 27906507

VL - 10

SP - 675

EP - 680

JO - CHEMSUSCHEM

JF - CHEMSUSCHEM

SN - 1864-5631

IS - 4

ER -