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Copper-Promoted Regioselective Synthesis of Polysubstituted Pyrroles from Aldehydes, Amines, and Nitroalkenes via 1,2-Phenyl/Alkyl Migration

Dimitrios Andreou, Michael G. Kallitsakis, Edward Loukopoulos, Catherine Gabriel, George E. Kostakis* and Ioannis N. Lykakis*

*School of Life Sciences, University of Sussex, Brighton BN19QJ, United Kingdom; Aristotle University of Thessaloniki, Thessaloniki 54124, Greece, Email: g.kostakissussex.ac.uk, lykakis@chem.auth.gr

D. Andreou, M. G. Kallitsakis, E. Loukopoulos, C. Gabries, G. E. Kostakis, J. N. Lykakis, J. Org. Chem., 2018, 83, 2104-2113.

DOI: 10.1021/acs.joc.7b03051 (free Supporting Information)


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Abstract

Copper catalysis enables the synthesis of polysubstituted pyrroles from aldehydes, amines, and β-nitroalkenes. Remarkably, the use of α-methyl-substituted aldehydes provides efficient access to a series of tetra- and pentasubstituted pyrroles via an overwhelming 1,2-phenyl/alkyl migration. Non α-substituted aldehydes provide the corresponding trisubstituted pyrroles.

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CuII-based coordinaation polymer with 1-{2-[1H-benzo[d][1,2,3]triazol-1-yl)methyl]-benzyl}1H-benzo[d][1,2,3]triazole as ligand

proposed mechanism



Key Words

pyrroles, multicomponent reactions


ID: J42-Y2018