Taming reactive phenol tautomers and o-quinone methides with transition metals: a structure-reactivity relationship.
Quinone methides act as important intermediates in organic syntheses, as well as in chemical and biological processes; however, examples of such isolated species are scarce as a result of their high reactivity. Phenol tautomers (keto form of phenol) are also important intermediates in several organic and organometallic reactions; nevertheless, isolated complexes are rare. This Account reviews the recent progress on the synthesis and reactivity of iridium and rhodium o-quinone methide complexes as well as on iridium-mediated ortho functionalization of phenols. This reaction was at the origin of the discovery of a general synthetic procedure to prepare the first metal-stabilized o-quinone methide.
Laboratoire de Chimie Inorganique et Matériaux, Moléculaires UMR 7071-CNRS, Université Pierre et Marie Curie, 4, place Jussieu, case 42, 75252 Paris Cedex 05, France. amouri@ccr.jussieu.fr
Hani
H
Amouri
Jean
J
Le Bras
D045563:Indolequinones; D007211:Indoles / Q000737:chemistry*; D008670:Metals / Q000737:chemistry; D008745:Methylation; D008958:Models, Molecular; D008968:Molecular Conformation; D019800:Phenol / Q000737:chemistry*; D011809:Quinones / Q000737:chemistry*; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
D045563:Indolequinones; D007211:Indoles; D008670:Metals; D011809:Quinones; C068040:quinone methide; D019800:Phenol