meta-Selective olefination of fluoroarenes with alkynes using CO2 as a traceless directing group

Over the last few decades C-H olefination has received significant interest, due to the importance and usefulness of aryl olefins both as synthetic targets and intermediates. While a wide range of ortho-olefination protocols have been developed, only a small number of meta-olefinations are currently...

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Bibliographic Details
Published in:Chemical science (Cambridge) Vol. 11; no. 16; pp. 4204 - 4208
Main Authors: Spencer, Andrew R. A., Korde, Rishi, Font, Marc, Larrosa, Igor
Format: Journal Article
Language:English
Published: CAMBRIDGE Royal Soc Chemistry 31.03.2020
Royal Society of Chemistry
The Royal Society of Chemistry
Subjects:
Alkenes
Alkynes
Aromatic compounds
Carbon dioxide
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Regioselectivity
Science & Technology
Substrates
CARBOXYLATES
ORGANOMETALLIC CHEMISTRY
ARYLATION
ARENES
FLUORINE
BOND ACTIVATION
C-H FUNCTIONALIZATION
DERIVATIVES
HYDROARYLATION
ALKENYLATION
ISSN:2041-6520, 2041-6539
Online Access:Get full text
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Summary:Over the last few decades C-H olefination has received significant interest, due to the importance and usefulness of aryl olefins both as synthetic targets and intermediates. While a wide range of ortho-olefination protocols have been developed, only a small number of meta-olefinations are currently available. Importantly, the most common approach to meta-olefination, using a large meta-directing template, is not suitable for substrates such as fluorobenzenes, which cannot be derivatised. We report that the meta-selective olefination of fluoroarenes can be achieved via the use of CO2 as a traceless directing group, which can be easily installed and removed in a one-pot process. Furthermore, this approach avoids the use of stoichiometric Ag(i)-salts, commonly used in C-H olefinations, and affords complete meta- over ortho/para-regioselectivity.
Bibliography:UKRI
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ISSN:2041-6520
2041-6539
DOI:10.1039/d0sc01138j