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Efficient Preparation of the Isoindoline Framework via a Six Component, Tandem Double A 3 ‐Coupling and [2+2+2] Cycloaddition Reaction
Author(s) -
Bonfield E. Ryan,
Li ChaoJun
Publication year - 2008
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.200700500
Subject(s) - cycloaddition , isoindoline , chemistry , alkyne , tandem , aldehyde , catalysis , amine gas treating , combinatorial chemistry , cascade reaction , bromide , coupling reaction , organic chemistry , materials science , composite material
The preparation of tetrasubstituted isoindolines from three alkyne units, two aldehyde units and a primary amine via three consecutive reactions, two aldehyde‐amine‐alkyne couplings (A 3 ‐couplings) and a final [2+2+2] cycloaddition, in a single synthetic operation, is described. The A 3 ‐couplings are catalyzed by copper bromide and the cycloaddition is catalyzed by Wilkinson’s catalyst. It was found that many catalysts known to be efficient at the cycloaddition step were not suitable when this step was part of the tandem reaction sequence. Wilkinson’s catalyst was found to be unique in its suitability for the overall domino reaction sequence.