Altering Copper‐Catalyzed A3 Couplings by Mechanochemistry: One‐Pot Synthesis of 1,4‐Diamino‐2‐butynes from Aldehydes, Amines, and Calcium Carbide

The ability of mechanochemistry to alter established chemical selectivity is demonstrated. A copper(I)‐catalyzed mechanochemical aldehyde/alkyne/amine coupling using calcium carbide as the acetylene source provides selective access to 1,4‐diamino‐2‐butynes, which contrasts classical approaches that...

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Published inAngewandte Chemie Vol. 130; no. 33; pp. 10878 - 10882
Main Authors Turberg, Mathias, Ardila‐Fierro, Karen J., Bolm, Carsten, Hernández, José G.
Format Journal Article
LanguageEnglish
Japanese
Published Weinheim Wiley Subscription Services, Inc 13.08.2018
Subjects
1,4-Diamino-2-butine
Acetylene
Aldehydes
Alkine
Alkynes
Amine
Amines
Calcium
Calciumcarbid
Carbides
Chemical synthesis
Chemistry
Copper
Couplings
Mechanochemie
Organic chemistry
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Summary:The ability of mechanochemistry to alter established chemical selectivity is demonstrated. A copper(I)‐catalyzed mechanochemical aldehyde/alkyne/amine coupling using calcium carbide as the acetylene source provides selective access to 1,4‐diamino‐2‐butynes, which contrasts classical approaches that provide propargylamine‐type products. Solventless milling conditions were found to be essential to unmask A3 coupling products with new compositions. Anders ist besser: Die mechanochemische Aktivierung von Aldehyden, Aminen und Calciumcarbid in Gegenwart von Kupfer(I)iodid ermöglicht die Synthese von 1,4‐Diamino‐2‐butinen unter solvensfreien Bedingungen.
Bibliography:These authors contributed equally to this work.
ISSN:0044-8249
1521-3757
DOI:10.1002/ange.201805505