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Photoelectrocatalytic Arene C-H Amination.

ABSTRACT: Photoelectrochemical cells are widely studied for solar energy conversion. However, they have rarely been used for the synthesis of high added-value organic molecules. Here we describe a strategy to use hematite, an abundant and robust photoanode, for non-directed arene C-H amination. Under illumination the photo generated holes in hematite oxidizes electron-rich arenes to radical cations which further react with azoles to give nitrogen heterocycles of medicinal interest. Unusual ortho-selectivity has been achieved probably due to a hydrogen bonding interaction between the substrates and the hexafluoroisopropanol co-solvent. The method exhibits broad scope and is successfully applied for the late-stage functionalization of several pharmaceutical molecules.

SUBMITTER: Zhang L

PROVIDER: S-EPMC6459354 | biostudies-literature | 2019 Apr

REPOSITORIES: biostudies-literature

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Photoelectrocatalytic Arene C-H Amination.

Zhang Lei L Liardet Laurent L Luo Jingshan J Ren Dan D Grätzel Michael M Hu Xile X

Nature catalysis 20190218 4

Photoelectrochemical cells are widely studied for solar energy conversion. However, they have rarely been used for the synthesis of high added-value organic molecules. Here we describe a strategy to use hematite, an abundant and robust photoanode, for non-directed arene C-H amination. Under illumination the photo generated holes in hematite oxidizes electron-rich arenes to radical cations which further react with azoles to give nitrogen heterocycles of medicinal interest. Unusual ortho-se ...[more]

PMID: 30984910

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