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Electrochemical Proton Reduction over Nickel Foam for Z ‐Stereoselective Semihydrogenation/deuteration of Functionalized Alkynes
Author(s) -
Valiente Alejandro,
MartínezPardo Pablo,
Kaur Gurpreet,
Johansson Magnus J.,
MartínMatute Belén
Publication year - 2022
Publication title -
chemsuschem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 2.412
H-Index - 157
eISSN - 1864-564X
pISSN - 1864-5631
DOI - 10.1002/cssc.202102221
Subject(s) - catalysis , nickel , electrocatalyst , electrochemistry , chemistry , aryl , stereoselectivity , combinatorial chemistry , organic chemistry , electrode , alkyl
Selective reduction strategies based on abundant‐metal catalysts are very important in the production of chemicals. In this paper, a method for the electrochemical semihydrogenation and semideuteration of alkynes to form Z ‐alkenes was developed, using a simple nickel foam as catalyst and H 3 O + or D 3 O + as sources of hydrogen or deuterium. Good yields and excellent stereoselectivities ( Z / E up to 20 : 1) were obtained under very mild reaction conditions. The reaction proceeded with terminal and nonterminal alkynes, and also with alkynes containing easily reducible functional groups, such as carbonyl groups, as well as aryl chlorides, bromides, and even iodides. The nickel‐foam electrocatalyst could be recycled up to 14 times without any change in its catalytic properties.