Insights into the Scholl Coupling Reaction: A Key Transformation of Relevance to the Synthesis of Graphenes and Related Systems

Mark S. Little; Stephen G. Yeates; Aula A. Alwattar; Kane W. J. Heard; James Raftery; Alyn C. Edwards; Adam. V. S. Parry; Peter Quayle

doi:10.1002/ejoc.201601580

Insights into the Scholl Coupling Reaction: A Key Transformation of Relevance to the Synthesis of Graphenes and Related Systems

Mark S. Little, Stephen G. Yeates, Aula A. Alwattar, Kane W. J. Heard, James Raftery, Alyn C. Edwards, Adam. V. S. Parry, Peter Quayle

Division of Population Health, Health Services Research & Primary Care (L5)

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Abstract

The use of Scholl-type reactions on 4,10-di-substituted chrysene derivatives proceeds via variegated, and unexpected oxidation/coupling pathways. These observations serve as a cautionary note when attempting to employ the Scholl reaction in target-oriented, materials, synthesis.

Original language	English
Pages (from-to)	1694-1703
Journal	European Journal of Organic Chemistry
Issue number	13
Early online date	30 Jan 2017
DOIs	https://doi.org/10.1002/ejoc.201601580
Publication status	Published - 3 Apr 2017

Keywords

Scholl reactions
Oxidation
Cross-coupling
Dimerization
Fused-ring systems

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10.1002/ejoc.201601580

Quayle Scholl paper EJOCAccepted author manuscript, 2.23 MB

CCDC 1413513: Experimental Crystal Structure Determination
Quayle, P. (Contributor), Little, M. (Contributor), Yeates, S. (Contributor), Rafter, J. (Contributor), Parry, A. (Contributor) & Edwards, A. C. (Contributor), Cambridge Crystallographic Data Centre, 1 Jan 2015
DOI: 10.5517/cc1jfw61, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/cc1jfw61&sid=DataCite
Dataset
CCDC 1413515: Experimental Crystal Structure Determination
Little, M. (Contributor), Yeates, S. (Contributor), Alwattar, A. (Contributor), Heard, K. (Contributor), Raftery, J. (Contributor), Edwards, A. (Contributor), Parry, A. (Contributor) & Quayle, P. (Contributor), Cambridge Crystallographic Data Centre, 1 Jan 2017
DOI: 10.5517/ccdc.csd.cc1jfw83, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cc1jfw83&sid=DataCite
Dataset
CCDC 1062056: Experimental Crystal Structure Determination
Little, M. (Contributor), Yeates, S. (Contributor), Alwattar, A. (Contributor), Heard, K. (Contributor), Raftery, J. (Contributor), Edwards, A. (Contributor), Parry, A. (Contributor) & Quayle, P. (Contributor), Cambridge Crystallographic Data Centre, 1 Jan 2015
DOI: 10.5517/ccdc.csd.cc14n4wt, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cc14n4wt&sid=DataCite
Dataset

Cite this

@article{59e6e5ade2fd4fa195bb098c4e62a4fa,

title = "Insights into the Scholl Coupling Reaction: A Key Transformation of Relevance to the Synthesis of Graphenes and Related Systems",

abstract = "The use of Scholl-type reactions on 4,10-di-substituted chrysene derivatives proceeds via variegated, and unexpected oxidation/coupling pathways. These observations serve as a cautionary note when attempting to employ the Scholl reaction in target-oriented, materials, synthesis.",

keywords = "Scholl reactions, Oxidation, Cross-coupling, Dimerization, Fused-ring systems",

author = "Little, {Mark S.} and Yeates, {Stephen G.} and Alwattar, {Aula A.} and Heard, {Kane W. J.} and James Raftery and Edwards, {Alyn C.} and Parry, {Adam. V. S.} and Peter Quayle",

year = "2017",

month = apr,

day = "3",

doi = "10.1002/ejoc.201601580",

language = "English",

pages = "1694--1703",

journal = "European Journal of Organic Chemistry",

issn = "1434-193X",

publisher = "John Wiley & Sons Ltd",

number = "13",

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TY - JOUR

T1 - Insights into the Scholl Coupling Reaction: A Key Transformation of Relevance to the Synthesis of Graphenes and Related Systems

AU - Little, Mark S.

AU - Yeates, Stephen G.

AU - Alwattar, Aula A.

AU - Heard, Kane W. J.

AU - Raftery, James

AU - Edwards, Alyn C.

AU - Parry, Adam. V. S.

AU - Quayle, Peter

PY - 2017/4/3

Y1 - 2017/4/3

N2 - The use of Scholl-type reactions on 4,10-di-substituted chrysene derivatives proceeds via variegated, and unexpected oxidation/coupling pathways. These observations serve as a cautionary note when attempting to employ the Scholl reaction in target-oriented, materials, synthesis.

AB - The use of Scholl-type reactions on 4,10-di-substituted chrysene derivatives proceeds via variegated, and unexpected oxidation/coupling pathways. These observations serve as a cautionary note when attempting to employ the Scholl reaction in target-oriented, materials, synthesis.

KW - Scholl reactions

KW - Oxidation

KW - Cross-coupling

KW - Dimerization

KW - Fused-ring systems

U2 - 10.1002/ejoc.201601580

DO - 10.1002/ejoc.201601580

M3 - Article

SP - 1694

EP - 1703

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

SN - 1434-193X

IS - 13

ER -

Insights into the Scholl Coupling Reaction: A Key Transformation of Relevance to the Synthesis of Graphenes and Related Systems

Abstract

Keywords

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Datasets

CCDC 1413513: Experimental Crystal Structure Determination

CCDC 1413515: Experimental Crystal Structure Determination

CCDC 1062056: Experimental Crystal Structure Determination

Cite this