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Superbase‐Promoted Addition of Acetylene Gas to the C=N Bond
Author(s) -
Schmidt Elena Yu.,
Bidusenko Ivan A.,
Protsuk Nadezhda I.,
Demyanov Yan V.,
Ushakov Igor A.,
Trofimov Boris A.
Publication year - 2019
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201900932
Subject(s) - superbase , chemistry , acetylene , triple bond , yield (engineering) , nitrogen , medicinal chemistry , organic chemistry , double bond , catalysis , thermodynamics , physics
A new Csp 3 –Csp bond forming reaction is reported: the C=N bond of widespread imines reacts with acetylene gas in the presence of superbase KO t Bu/DMSO at room temperature to afford terminal α‐aminoacetylenes in up to 94 % yield. The reaction allows nitrogen heterocycles, e.g. 3H‐indoles, to be directly cross‐coupled with acetylene gas.