Abstract
We demonstrate that aryltriazenes can promote three distinctive types of C–H functionalization reactions, allowing the preparation of complex benzene molecules with diverse substitution patterns. 2-Triazenylbenzaldehydes are shown to be efficient substrates for Rh(I)-catalyzed intermolecular alkyne hydroacylation reactions. The resulting triazene-substituted ketone products can then undergo either a Rh(III)-catalyzed C–H activation, or an electrophilic aromatic substitution reaction, achieving multifunctionalization of the benzene core. Subsequent triazene derivatization provides traceless products.
Highlights
We demonstrate that aryltriazenes can promote three distinctive types of C−H functionalization reactions, allowing the preparation of complex benzene molecules with diverse substitution patterns. 2-Triazenylbenzaldehydes are shown to be efficient substrates for Rh(I)-catalyzed intermolecular alkyne hydroacylation reactions
Aldehydes featuring P,10 O,11 N,12 and S-based chelating groups,[13] as well as chelating alkenes,[14] have all been used, and reactions that proceed under mild reaction conditions and encompass broad substrate scopes have been achieved
Approaches have been developed where the chelating group is either incorporated into a target structure,18f,19 or transformed to an alternate functionality.18g,20 For example, our laboratory has shown that a chelating methyl sulfide employed in hydroacylation reactions can be directly utilized in subsequent Rh-catalyzed carbothiolation, arylation, or reduction reactions.[21]
Summary
We demonstrate that aryltriazenes can promote three distinctive types of C−H functionalization reactions, allowing the preparation of complex benzene molecules with diverse substitution patterns. 2-Triazenylbenzaldehydes are shown to be efficient substrates for Rh(I)-catalyzed intermolecular alkyne hydroacylation reactions.
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