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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| Published in: | Chemical science (Cambridge) Vol. 11; no. 16; pp. 4204 - 4208 |
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| Main Authors: | , , , |
| Format: | Journal Article |
| Language: | English |
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Royal Soc Chemistry
31.03.2020
Royal Society of Chemistry The Royal Society of Chemistry |
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| ISSN: | 2041-6520, 2041-6539 |
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| Abstract | 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. |
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| AbstractList | 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. A transient directing group approach using CO2 facilitates the direct meta-olefination of fluorobenzenes with alkynes. 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.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. 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. |
| Author | Larrosa, Igor Font, Marc Spencer, Andrew R. A. Korde, Rishi |
| Author_xml | – sequence: 1 givenname: Andrew R. A. surname: Spencer fullname: Spencer, Andrew R. A. organization: Univ Manchester, Sch Chem, Oxford Rd, Manchester M13 9PL, Lancs, England – sequence: 2 givenname: Rishi surname: Korde fullname: Korde, Rishi organization: Univ Manchester, Sch Chem, Oxford Rd, Manchester M13 9PL, Lancs, England – sequence: 3 givenname: Marc orcidid: 0000-0002-4536-265X surname: Font fullname: Font, Marc organization: Univ Manchester, Sch Chem, Oxford Rd, Manchester M13 9PL, Lancs, England – sequence: 4 givenname: Igor orcidid: 0000-0002-5391-7424 surname: Larrosa fullname: Larrosa, Igor email: igor.larrosa@manchester.ac.uk organization: Univ Manchester, Sch Chem, Oxford Rd, Manchester M13 9PL, Lancs, England |
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| Keywords | CARBOXYLATES ORGANOMETALLIC CHEMISTRY ARYLATION ARENES FLUORINE BOND ACTIVATION C-H FUNCTIONALIZATION DERIVATIVES HYDROARYLATION ALKENYLATION |
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| SubjectTerms | Alkenes Alkynes Aromatic compounds Carbon dioxide Chemistry Chemistry, Multidisciplinary Physical Sciences Regioselectivity Science & Technology Substrates |
| Title | meta-Selective olefination of fluoroarenes with alkynes using CO2 as a traceless directing group |
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