Catalytic constructive deoxygenation of lignin-derived phenols: new C-C bond formation processes from imidazole-sulfonates and ether cleavage reactions

Stuart M. Leckie; Gavin J. Harkness; Matthew L. Clarke

doi:10.1039/C4CC04939J

Catalytic constructive deoxygenation of lignin-derived phenols: new C-C bond formation processes from imidazole-sulfonates and ether cleavage reactions

Stuart M. Leckie, Gavin J. Harkness, Matthew L. Clarke

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

Abstract

As part of a programme aimed at exploiting lignin as a chemical feedstock for less oxygenated fine chemicals, several catalytic C-C bond forming reactions utilising guaiacol imidazole sulfonate are demonstrated. These include the cross-coupling of a Grignard, a non-toxic cyanide source, a benzoxazole, and nitromethane. A modified Meyers reaction is used to accomplish a second constructive deoxygenation on a benzoxazole functionalised anisole.

Original language	English
Pages (from-to)	11511-11513
Number of pages	3
Journal	Chemical Communications
Volume	50
Issue number	78
Early online date	12 Aug 2014
DOIs	https://doi.org/10.1039/C4CC04939J
Publication status	Published - 9 Oct 2014

Access to Document

10.1039/C4CC04939J

leckie2014chemcomm11511
© 2014. The Royal Society of Chemistry. This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.
Final published version, 1.38 MB

Cite this

@article{1256ccd82aa24197850f6e27ab612c2b,

title = "Catalytic constructive deoxygenation of lignin-derived phenols: new C-C bond formation processes from imidazole-sulfonates and ether cleavage reactions",

abstract = "As part of a programme aimed at exploiting lignin as a chemical feedstock for less oxygenated fine chemicals, several catalytic C-C bond forming reactions utilising guaiacol imidazole sulfonate are demonstrated. These include the cross-coupling of a Grignard, a non-toxic cyanide source, a benzoxazole, and nitromethane. A modified Meyers reaction is used to accomplish a second constructive deoxygenation on a benzoxazole functionalised anisole.",

author = "Leckie, \{Stuart M.\} and Harkness, \{Gavin J.\} and Clarke, \{Matthew L.\}",

note = "Funding: UK Engineering and Physical Sciences Research Council (EPSRC)",

year = "2014",

month = oct,

day = "9",

doi = "10.1039/C4CC04939J",

language = "English",

volume = "50",

pages = "11511--11513",

journal = "Chemical Communications",

issn = "1359-7345",

publisher = "Royal Society of Chemistry",

number = "78",

}

TY - JOUR

T1 - Catalytic constructive deoxygenation of lignin-derived phenols: new C-C bond formation processes from imidazole-sulfonates and ether cleavage reactions

AU - Leckie, Stuart M.

AU - Harkness, Gavin J.

AU - Clarke, Matthew L.

N1 - Funding: UK Engineering and Physical Sciences Research Council (EPSRC)

PY - 2014/10/9

Y1 - 2014/10/9

N2 - As part of a programme aimed at exploiting lignin as a chemical feedstock for less oxygenated fine chemicals, several catalytic C-C bond forming reactions utilising guaiacol imidazole sulfonate are demonstrated. These include the cross-coupling of a Grignard, a non-toxic cyanide source, a benzoxazole, and nitromethane. A modified Meyers reaction is used to accomplish a second constructive deoxygenation on a benzoxazole functionalised anisole.

AB - As part of a programme aimed at exploiting lignin as a chemical feedstock for less oxygenated fine chemicals, several catalytic C-C bond forming reactions utilising guaiacol imidazole sulfonate are demonstrated. These include the cross-coupling of a Grignard, a non-toxic cyanide source, a benzoxazole, and nitromethane. A modified Meyers reaction is used to accomplish a second constructive deoxygenation on a benzoxazole functionalised anisole.

UR - http://dx.doi.org/10.1039/C4CC04939J

UR - https://www.scopus.com/pages/publications/84929600979

U2 - 10.1039/C4CC04939J

DO - 10.1039/C4CC04939J

M3 - Article

SN - 1359-7345

VL - 50

SP - 11511

EP - 11513

JO - Chemical Communications

JF - Chemical Communications

IS - 78

ER -

Catalytic constructive deoxygenation of lignin-derived phenols: new C-C bond formation processes from imidazole-sulfonates and ether cleavage reactions

Abstract

Access to Document

Other files and links

Fingerprint

Clean catalysis for sustainable develop: Clean catalysis for sustainable development

Clean catalysis for sustainable develop: Clean catalysis for sustainable development

Sequential processes using catalytic C-O bond activation

Cite this

Catalytic constructive deoxygenation of lignin-derived phenols: new C-C bond formation processes from imidazole-sulfonates and ether cleavage reactions

Abstract

Access to Document

Other files and links

Fingerprint

Projects

Clean catalysis for sustainable develop: Clean catalysis for sustainable development

Clean catalysis for sustainable develop: Clean catalysis for sustainable development

Student theses

Sequential processes using catalytic C-O bond activation

Cite this