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Highly Regioselective Synthesis of Substituted Isoindolinones via Ruthenium‐Catalyzed Alkyne Cyclotrimerizations
Author(s) -
Foster Robert W.,
Tame Christopher J.,
Hailes Helen C.,
Sheppard Tom D.
Publication year - 2013
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.201300055
Subject(s) - regioselectivity , chemistry , alkyne , ruthenium , amide , catalysis , trimethylsilyl , ring (chemistry) , medicinal chemistry , combinatorial chemistry , organic chemistry
(Cyclooctadiene)(pentamethylcyclopentadiene)ruthenium chloride [Cp*RuCl(cod)] has been used to catalyze the regioselective cyclization of amide‐tethered diynes with monosubstituted alkynes to give polysubstituted isoindolinones. Notably, the presence of a trimethylsilyl group on the diyne generally led to complete control over the regioselectivity of the alkyne cyclotrimerization. The cyclization reaction worked well in a sustainable non‐chlorinated solvent and was tolerant of moisture. The optimized conditions were effective with a diverse range of alkynes and diynes. The 7‐silylisoindolinone products could be halogenated, protodesilylated or ring opened to access a range of usefully functionalized products.