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C-H Oxygenation Reactions Enabled by Dual Catalysis with Electrogenerated Hypervalent Iodine Species and Ruthenium Complexes.

ABSTRACT: The catalytic generation of hypervalent iodine(III) reagents by anodic electrooxidation was orchestrated towards an unprecedented electrocatalytic C-H oxygenation of weakly coordinating aromatic amides and ketones. Thus, catalytic quantities of iodoarenes in concert with catalytic amounts of ruthenium(II) complexes set the stage for versatile C-H activations with ample scope and high functional group tolerance. Detailed mechanistic studies by experiment and computation substantiate the role of the iodoarene as the electrochemically relevant species towards C-H oxygenations with electricity as a sustainable oxidant and molecular hydrogen as the sole by-product. para-Selective C-H oxygenations likewise proved viable in the absence of directing groups.

SUBMITTER: Massignan L

PROVIDER: S-EPMC7027769 | biostudies-literature | 2020 Feb

REPOSITORIES: biostudies-literature

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C-H Oxygenation Reactions Enabled by Dual Catalysis with Electrogenerated Hypervalent Iodine Species and Ruthenium Complexes.

Massignan Leonardo L Tan Xuefeng X Meyer Tjark H TH Kuniyil Rositha R Messinis Antonis M AM Ackermann Lutz L

Angewandte Chemie (International ed. in English) 20200109 8

The catalytic generation of hypervalent iodine(III) reagents by anodic electrooxidation was orchestrated towards an unprecedented electrocatalytic C-H oxygenation of weakly coordinating aromatic amides and ketones. Thus, catalytic quantities of iodoarenes in concert with catalytic amounts of ruthenium(II) complexes set the stage for versatile C-H activations with ample scope and high functional group tolerance. Detailed mechanistic studies by experiment and computation substantiate the role of t ...[more]

PMID: 31777143

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