Arene activation via π-bond localization: concepts and opportunities
Paul Meiners, Julian J Melder, Tobias Morack
TL;DR
This review explores strategies to activate aromatic compounds by disrupting their π-bonds, offering new ways to synthesize complex molecules.
Contribution
The paper introduces π-bond localization as a general strategy for arene activation and dearomatization.
Findings
Four approaches to π-bond localization are analyzed for their structural and reactivity effects.
Examples of both stoichiometric and catalytic applications are provided to demonstrate synthetic utility.
The concepts offer a roadmap for developing new methods in aromatic compound synthesis.
Abstract
Dearomatization reactions of aromatic feedstocks constitute a highly efficient and conceptually powerful class of transformations for the synthesis of complex, three-dimensional molecular architectures with tailored physicochemical properties. Despite notable advances in dearomative methodologies over the past decades, the selective and controlled disruption of the aromatic core continues to represent a fundamental challenge in synthetic chemistry. In this review, we delineate the potential of π-bond localization within the aromatic framework as a general strategy for arene activation and dearomatization. Four distinct approaches are discussed, encompassing localization of the arene π-bonds through small-ring annelation as well as transition metal coordination to aromatic fragments in an η2-, η3-, and η4-fashion. The structural and reactivity consequences of these perturbations are…
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Taxonomy
TopicsCatalytic C–H Functionalization Methods · Catalytic Cross-Coupling Reactions · Organoboron and organosilicon chemistry