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Oligosubstituted Pyrroles Directly from Substituted Methyl Isocyanides and Acetylenes
Author(s) -
Lygin Alexander V.,
Larionov Oleg V.,
Korotkov Vadim S.,
de Meijere Armin
Publication year - 2008
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200801395
Subject(s) - cycloaddition , chemistry , yield (engineering) , triple bond , rationalization (economics) , combinatorial chemistry , medicinal chemistry , organic chemistry , double bond , catalysis , materials science , philosophy , epistemology , metallurgy
The formal cycloaddition of α‐metallated methyl isocyanides 1 onto the triple bond of electron‐deficient acetylenes 2 represents a direct and convenient approach to oligosubstituted pyrroles 3 . The scope and limitations of this reaction (24 examples, 25–97 % yield) are reported along with an optimization of the reaction conditions and a rationalization of the mechanism. In addition, a related newly developed Cu I ‐mediated synthesis of 2,3‐disubstituted pyrroles by the reaction of copper acetylides derived from unactivated terminal alkynes with substituted methyl isocyanides is described (11 examples, 5–88 %yield).