Visible-Light Photocatalytic Synthesis of Amines from Imines via Transfer Hydrogenation Using Quantum Dots as Catalysts

The Journal of Organic Chemistry
Zi-Wei XiXiao-Gang Peng

Abstract

CdSe/CdS core/shell quantum dots (QDs) can be used as stable and highly active photoredox catalysts for efficient transfer hydrogenation of imines to amines with thiophenol as a hydrogen atom donor. This reaction proceeds via a proton-coupled electron transfer (PCET) from the QDs conduction band to the protonated imine followed by hydrogen atom transfer from the thiophenol to the α-aminoalkyl radical. This precious metal free transformation is easy to scale up and can be carried out by a one-pot protocol directly from aldehyde, amine, and thiophenol.  Additional advantageous features of this protocol include a wide substrate scope, high yield of the amine products, extremely low catalyst loading (0.001 mol %), high turnover number (105), and the mild reaction conditions of using visible light or sun light at room temperature in neutral media.

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Citations

May 17, 2019·Chemical Society Reviews·Jin-Dong YangJin-Pei Cheng
Jul 1, 2020·Beilstein Journal of Organic Chemistry·Shrikant D TambeEun Jin Cho
Jul 27, 2021·The Journal of Physical Chemistry Letters·Yucheng YuanOu Chen

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