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Continuous‐Flow Hydrogenation and Reductive Deuteration of Nitriles: a Simple Access to α,α‐Dideutero Amines
Author(s) -
Mészáros Rebeka,
Peng BaiJing,
Ötvös Sándor B.,
Yang ShyhChyun,
Fülöp Ferenc
Publication year - 2019
Publication title -
chempluschem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.801
H-Index - 61
ISSN - 2192-6506
DOI - 10.1002/cplu.201900526
Subject(s) - chemistry , yield (engineering) , deuterium , raney nickel , reductive amination , continuous flow , catalysis , combinatorial chemistry , reductive elimination , flow chemistry , nitrile , organic chemistry , physics , materials science , quantum mechanics , mechanics , metallurgy
A simple and efficient continuous flow methodology has been developed for hydrogenation and reductive deuteration of nitriles to yield primary amines and also valuable α,α‐dideutero analogues. Raney nickel proved to be a useful catalyst for the transformation of a wide range of nitriles under reasonably mild conditions with excellent deuterium incorporation (>90 %) and quantitative conversion. Among known model compounds, three new deuterated primary amines were prepared. The large‐scale synthesis of deuterated tryptamine was also carried out to deliver 1.1 g product under flow conditions.