Visible Light-Enhanced C−H Amination of Cyclic Ethers with Iminoiodinanes

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Abstract

A two-step protocol allowing the C−H amination of cyclic ethers with iminoiodinanes, followed by the reduction of the resulting intermediate has been developed for the preparation of amino alcohols. The initial C−H functionalization is accelerated by visible light, improving the reactivity compared to the thermal process performed in the dark. The effect of different substituents on the ...

Abstract

A two-step protocol allowing the C−H amination of cyclic ethers with iminoiodinanes, followed by the reduction of the resulting intermediate has been developed for the preparation of amino alcohols. The initial C−H functionalization is accelerated by visible light, improving the reactivity compared to the thermal process performed in the dark. The effect of different substituents on the photochemical reactivity of iminoiodinanes has been studied both experimentally and computationally. Photophysical measurements and DFT calculations were performed to better understand the observed reactivities and corroborate the proposed mechanistic proposal.