One-pot H/D exchange and low-coordinated iron electrocatalyzed deuteration of nitriles in D2O to α,β-deuterio aryl ethylamines

Rui Li, Yongmeng Wu, Changhong Wang, Meng He, Cuibo Liu () and Bin Zhang ()
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Rui Li: Tianjin University
Yongmeng Wu: Tianjin University
Changhong Wang: Tianjin University
Meng He: Tianjin University
Cuibo Liu: Tianjin University
Bin Zhang: Tianjin University

Nature Communications, 2022, vol. 13, issue 1, 1-12

Abstract: Abstract Developing a step-economical approach for efficient synthesis of α,β-deuterio aryl ethylamines (α,β-DAEAs) with high deuterium ratios using an easy-to-handle deuterated source under ambient conditions is highly desirable. Here we report a room-temperature one-pot two-step transformation of aryl acetonitriles to α,β-DAEAs with up to 92% isolated yield and 99% α,β-deuterium ratios using D2O as a deuterium source. The process involves a fast α-C − H/C − D exchange and tandem electroreductive deuteration of C ≡ N over an in situ formed low-coordinated Fe nanoparticle cathode. The moderate adsorptions of nitriles/imine intermediates and the promoted formation of active hydrogen (H*) on unsaturated Fe sites facilitate the electroreduction process. In situ Raman confirms co-adsorption of aryl rings and the C ≡ N group on the Fe surface. A proposed H*-addition pathway is confirmed by the detected hydrogen and carbon radicals. Wide substrate scope, parallel synthesis of multiple α,β-DAEAs, and successful preparation of α,β-deuterated Melatonin and Komavine highlight the potential.

Date: 2022
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DOI: 10.1038/s41467-022-33779-8

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