Oligosubstituted pyrroles directly from substituted methyl isocyanides and acetylenes

AV Lygin, OV Larionov, VS Korotkov…

Index: Lygin, Alexander V.; Larionov, Oleg V.; Korotkov, Vadim S.; De Meijere, Armin Chemistry - A European Journal, 2009 , vol. 15, # 1 p. 227 - 236

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Citation Number: 69

Abstract

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 Cu I-mediated synthesis of 2, 3- ...