Scope and limitations of a DMF bio-alternative within Sonogashira cross-coupling and Cacchi-type annulation

Kirsty Wilson; Alan Kennedy; Jane Murray; Ben Greatex; Craig Jamieson; Allan Watson

doi:10.3762/bjoc.12.187

Scope and limitations of a DMF bio-alternative within Sonogashira cross-coupling and Cacchi-type annulation

Kirsty Wilson
, Alan Kennedy
, Jane Murray
, Ben Greatex
, Craig Jamieson
, Allan Watson

School of Chemistry

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

Abstract

Pd-catalysed C-C bond formation is an essential tool within the pharmaceutical and agrochemical industries. Many of these reactions rely heavily on polar aprotic solvents; however, despite their utility, these solvents are incompatible with the drive towards more sustainable chemical synthesis. Herein, we describe the scope and limitations of an alternative to DMF derived from renewable sources (Cyrene^TM) in Sonogashira crosscoupling and Cacchi-type annulations.

Original language	English
Pages (from-to)	2005-2011
Number of pages	7
Journal	Beilstein Journal of Organic Chemistry
Volume	12
DOIs	https://doi.org/10.3762/bjoc.12.187
Publication status	Published - 8 Sept 2016

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

SDG 7 Affordable and Clean Energy

Keywords

Cacchi annulation
Cross-coupling
Heterocycles
Sonogashira
Sustainable solvent

Access to Document

10.3762/bjoc.12.187Licence: CC BY

Wilson_2016_BJOC_Sonogashira_CC
© 2016 Wilson et al.; licensee Beilstein-Institut. This is an Open Access article under the terms of the Creative Commons Attribution License (http://creativecommons.org/licenses/by/4.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
Final published version, 428 KBLicence: CC BY

Handle.net

Persistent link

Cite this

@article{c2155a441bb04f49866456cadccb53e2,

title = "Scope and limitations of a DMF bio-alternative within Sonogashira cross-coupling and Cacchi-type annulation",

abstract = "Pd-catalysed C-C bond formation is an essential tool within the pharmaceutical and agrochemical industries. Many of these reactions rely heavily on polar aprotic solvents; however, despite their utility, these solvents are incompatible with the drive towards more sustainable chemical synthesis. Herein, we describe the scope and limitations of an alternative to DMF derived from renewable sources (CyreneTM) in Sonogashira crosscoupling and Cacchi-type annulations.",

keywords = "Cacchi annulation, Cross-coupling, Heterocycles, Sonogashira, Sustainable solvent",

author = "Kirsty Wilson and Alan Kennedy and Jane Murray and Ben Greatex and Craig Jamieson and Allan Watson",

note = "We thank the University of Strathclyde for a PhD studentship (KLW), Sigma-Aldrich for financial and material support, Circa for Cyrene, and the EPSRC UK National Mass Spectrometry Facility at Swansea University for analyses.",

year = "2016",

month = sep,

day = "8",

doi = "10.3762/bjoc.12.187",

language = "English",

volume = "12",

pages = "2005--2011",

journal = "Beilstein Journal of Organic Chemistry",

issn = "1860-5397",

publisher = "Beilstein-Institut Zur Forderung der Chemischen Wissenschaften",

}

TY - JOUR

T1 - Scope and limitations of a DMF bio-alternative within Sonogashira cross-coupling and Cacchi-type annulation

AU - Wilson, Kirsty

AU - Kennedy, Alan

AU - Murray, Jane

AU - Greatex, Ben

AU - Jamieson, Craig

AU - Watson, Allan

N1 - We thank the University of Strathclyde for a PhD studentship (KLW), Sigma-Aldrich for financial and material support, Circa for Cyrene, and the EPSRC UK National Mass Spectrometry Facility at Swansea University for analyses.

PY - 2016/9/8

Y1 - 2016/9/8

N2 - Pd-catalysed C-C bond formation is an essential tool within the pharmaceutical and agrochemical industries. Many of these reactions rely heavily on polar aprotic solvents; however, despite their utility, these solvents are incompatible with the drive towards more sustainable chemical synthesis. Herein, we describe the scope and limitations of an alternative to DMF derived from renewable sources (CyreneTM) in Sonogashira crosscoupling and Cacchi-type annulations.

AB - Pd-catalysed C-C bond formation is an essential tool within the pharmaceutical and agrochemical industries. Many of these reactions rely heavily on polar aprotic solvents; however, despite their utility, these solvents are incompatible with the drive towards more sustainable chemical synthesis. Herein, we describe the scope and limitations of an alternative to DMF derived from renewable sources (CyreneTM) in Sonogashira crosscoupling and Cacchi-type annulations.

KW - Cacchi annulation

KW - Cross-coupling

KW - Heterocycles

KW - Sonogashira

KW - Sustainable solvent

U2 - 10.3762/bjoc.12.187

DO - 10.3762/bjoc.12.187

M3 - Article

SN - 1860-5397

VL - 12

SP - 2005

EP - 2011

JO - Beilstein Journal of Organic Chemistry

JF - Beilstein Journal of Organic Chemistry

ER -

Scope and limitations of a DMF bio-alternative within Sonogashira cross-coupling and Cacchi-type annulation

Abstract

UN SDGs

Keywords

Access to Document

Handle.net

Fingerprint

Cite this