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Solid‐Supported [2+2+2] Cyclotrimerizations
Author(s) -
Young Douglas D.,
Senaiar Ramesh S.,
Deiters Alexander
Publication year - 2006
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.200501360
Subject(s) - alkyne , cycloaddition , combinatorial chemistry , isoindoline , scope (computer science) , chemistry , molecule , reaction conditions , catalysis , solid phase synthesis , transition metal , computer science , organic chemistry , programming language , peptide , biochemistry
The transition‐metal‐catalyzed [2+2+2] cyclotrimerization of a diyne and an alkyne provides a convergent route to highly‐substituted aromatic rings. This reaction possesses distinct drawbacks, especially low chemo‐ and regioselectivities, which hamper its application in combinatorial synthesis. These problems have been solved by the development of solid‐supported [2+2+2]‐cycloaddition reactions. If conducted on a solid‐support, this reaction enables rapid combinatorial access to diverse sets of carbo‐ and heterocyclic small‐molecule arrays. The scope of this methodology has been investigated by examining different immobilization strategies, different diyne precursors, and a variety of functionalized alkyne reaction partners. Overall, isoindoline, phthalan, and indan libraries were assembled in good to excellent yields and with high purities.