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Rhodaelectro-Catalyzed peri-Selective Direct Alkenylations with Weak O-Coordination Enabled by the Hydrogen Evolution Reaction (HER).

ABSTRACT: Direct C-H functionalizations by electrocatalysis is dominated by strongly coordinating N(sp² )-directing groups. In sharp contrast, direct electrocatalytic transformations of weakly-coordinating phenols remain underdeveloped. Herein, electrooxidative peri C-H alkenylations of challenging 1-naphthols were achieved by versatile rhodium(III) catalysis via user-friendly constant current electrolysis. The rhodaelectrocatalysis employed readily-available alkenes and a protic reaction medium and features ample scope, good functional group tolerance and high site- and stereoselectivity. The strategy was successfully applied to high-value, nitrogen-containing heterocycles, thereby providing direct access to uncommon heterocyclic motifs based on the dihydropyranoquinoline skeleton.

SUBMITTER: Sadowski B

PROVIDER: S-EPMC9311442 | biostudies-literature | 2022 May

REPOSITORIES: biostudies-literature

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Rhodaelectro-Catalyzed peri-Selective Direct Alkenylations with Weak O-Coordination Enabled by the Hydrogen Evolution Reaction (HER).

Sadowski Bartłomiej B Yuan Binbin B Lin Zhipeng Z Ackermann Lutz L

Angewandte Chemie (International ed. in English) 20220314 20

Direct C-H functionalizations by electrocatalysis is dominated by strongly coordinating N(sp<sup>2</sup> )-directing groups. In sharp contrast, direct electrocatalytic transformations of weakly-coordinating phenols remain underdeveloped. Herein, electrooxidative peri C-H alkenylations of challenging 1-naphthols were achieved by versatile rhodium(III) catalysis via user-friendly constant current electrolysis. The rhodaelectrocatalysis employed readily-available alkenes and a protic reaction mediu ...[more]

PMID: 35179817

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