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Sequential Catalytic Functionalization of Aryltriazenyl Aldehydes for the Synthesis of Complex Benzenes.

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.

SUBMITTER: Seo S

PROVIDER: S-EPMC8291607 | biostudies-literature | 2021 May

REPOSITORIES: biostudies-literature

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Sequential Catalytic Functionalization of Aryltriazenyl Aldehydes for the Synthesis of Complex Benzenes.

Seo Sangwon S Gao Ming M Paffenholz Eva E Willis Michael C MC

ACS catalysis 20210505 10

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 m ...[more]

PMID: 34306807

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