The Aromatic Carbon-Carbon ipso-Substitution Reaction

• Published in: Chemistry : a European journal Vol. 16; no. 46; pp. 13572 - 13589
• Main Authors: Bonesi, Sergio M., Fagnoni, Maurizio
• Format: Journal Article
• Language: English
• Published: Weinheim WILEY-VCH Verlag 10.12.2010; WILEY‐VCH Verlag; Wiley Subscription Services, Inc
• Subjects: Ar-C bonds; aromatic substitution; arylation; Bonding; C-based leaving groups; Carbon; Carbon-carbon composites; Carbonyl groups; Chemistry; cleavage reactions; Expenses
• ISSN: 0947-6539; 1521-3765
• DOI: 10.1002/chem.201001478

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. Getting the bond back together: The strategies are unveiled for an aromatic CC ipso‐substitution reaction. This process allows for the one‐pot cleavage of ArC 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 ArC bond (see picture).