The Aromatic Carbon-Carbon ipso-Substitution Reaction
The aim of this review is to illustrate what we have dubbed an aromatic carbon–carbon ipso‐substitution reaction in which a new ArC bond is formed at the expense of another ArC bond. The potentiality of several C‐based leaving groups including alkyl, carbinol, CN, COOH, and carbonyl groups in aryl...
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| Published in | Chemistry : a European journal Vol. 16; no. 46; pp. 13572 - 13589 |
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| Main Authors | , |
| Format | Journal Article |
| Language | English |
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Weinheim
WILEY-VCH Verlag
10.12.2010
WILEY‐VCH Verlag Wiley Subscription Services, Inc |
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| Abstract | The aim of this review is to illustrate what we have dubbed an aromatic carbon–carbon ipso‐substitution reaction in which a new ArC bond is formed at the expense of another ArC bond. The potentiality of several C‐based leaving groups including alkyl, carbinol, CN, COOH, and carbonyl groups in arylation reactions will be illustrated accordingly for the preparation of biphenyl‐, vinyl‐, alkynyl‐, and alkyl‐substituted aromatics.
Getting the bond back together: The strategies are unveiled for an aromatic CC ipso‐substitution reaction. This process allows for the one‐pot cleavage of ArC bonds (e.g., in alkyl and acyl (hetero)aromatics, in benzonitriles, in α,α‐disubstituted arylmethanols, and in carboxylic acids) for the formation of a new ArC bond (see picture). |
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| AbstractList | The aim of this review is to illustrate what we have dubbed an aromatic carbon-carbon ipso-substitution reaction in which a new ArC bond is formed at the expense of another ArC bond. The potentiality of several C-based leaving groups including alkyl, carbinol, CN, COOH, and carbonyl groups in arylation reactions will be illustrated accordingly for the preparation of biphenyl-, vinyl-, alkynyl-, and alkyl-substituted aromatics. Abstract The aim of this review is to illustrate what we have dubbed an aromatic carbon–carbon ipso ‐substitution reaction in which a new ArC bond is formed at the expense of another ArC bond. The potentiality of several C‐based leaving groups including alkyl, carbinol, CN, COOH, and carbonyl groups in arylation reactions will be illustrated accordingly for the preparation of biphenyl‐, vinyl‐, alkynyl‐, and alkyl‐substituted aromatics. The aim of this review is to illustrate what we have dubbed an aromatic carbon–carbon ipso‐substitution reaction in which a new ArC bond is formed at the expense of another ArC bond. The potentiality of several C‐based leaving groups including alkyl, carbinol, CN, COOH, and carbonyl groups in arylation reactions will be illustrated accordingly for the preparation of biphenyl‐, vinyl‐, alkynyl‐, and alkyl‐substituted aromatics. Getting the bond back together: The strategies are unveiled for an aromatic CC ipso‐substitution reaction. This process allows for the one‐pot cleavage of ArC bonds (e.g., in alkyl and acyl (hetero)aromatics, in benzonitriles, in α,α‐disubstituted arylmethanols, and in carboxylic acids) for the formation of a new ArC bond (see picture). The aim of this review is to illustrate what we have dubbed an aromatic carbon-carbon ipso-substitution reaction in which a new Ar-C bond is formed at the expense of another Ar-C bond. The potentiality of several C-based leaving groups including alkyl, carbinol, CN, COOH, and carbonyl groups in arylation reactions will be illustrated accordingly for the preparation of biphenyl-, vinyl-, alkynyl-, and alkyl-substituted aromatics. |
| Author | Bonesi, Sergio M. Fagnoni, Maurizio |
| Author_xml | – sequence: 1 givenname: Sergio M. surname: Bonesi fullname: Bonesi, Sergio M. organization: CIHIDECAR-CONICET, Departamento de Química Orgánica, 3er Piso, Pabellón 2, Facultad de Ciencias Exactas y Naturales, Ciudad Universitaria, CP1428, Universidad de Buenos Aires (Argentina) – sequence: 2 givenname: Maurizio surname: Fagnoni fullname: Fagnoni, Maurizio email: fagnoni@unipv.it organization: Department of Organic Chemistry, University of Pavia, Via Taramelli 10 (Italy), Fax: (+39) 0382-987316 |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/20967901$$D View this record in MEDLINE/PubMed |
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| Snippet | The aim of this review is to illustrate what we have dubbed an aromatic carbon–carbon ipso‐substitution reaction in which a new ArC bond is formed at the... The aim of this review is to illustrate what we have dubbed an aromatic carbon-carbon ipso-substitution reaction in which a new Ar-C bond is formed at the... Abstract The aim of this review is to illustrate what we have dubbed an aromatic carbon–carbon ipso ‐substitution reaction in which a new ArC bond is formed... The aim of this review is to illustrate what we have dubbed an aromatic carbon-carbon ipso-substitution reaction in which a new ArC bond is formed at the... |
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| SubjectTerms | Ar-C bonds aromatic substitution arylation Bonding C-based leaving groups Carbon Carbon-carbon composites Carbonyl groups Chemistry cleavage reactions Expenses |
| Title | The Aromatic Carbon-Carbon ipso-Substitution Reaction |
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