Oligosubstituted Pyrroles Directly from Substituted Methyl Isocyanides and Acetylenes
- 18 December 2008
- journal article
- research article
- Published by Wiley in Chemistry – A European Journal
- Vol. 15 (1), 227-236
- https://doi.org/10.1002/chem.200801395
Abstract
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 CuI‐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).This publication has 131 references indexed in Scilit:
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