Mayur V. Khedkar, S. Khan, K. P. Dhake
Aug 1, 2012
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0
Influential Citations
14
Citations
Journal
Synthesis
Abstract
The carbonylative cyclization of o -iodobenzoic acid with a variety of primary amines and carbon monoxide (1 bar) using a polymer-supported palladium–N-heterocyclic carbene complex (PS-Pd-NHC) as the catalyst gives N-substituted 1 H -isoindole-1,3(2 H )-diones (phthalimides) in good to excellent yields with a short reaction time. The catalyst is efficient, heterogeneous, and phosphine-free, it exhibited remarkable activity and it is also recyclable (4 consecutive cycles). The use of methyl o -iodobenzoate as the substrate under these conditions also gave N-substituted 1 H -isoindole-1,3(2 H )-diones, but with lower yields. Cyclization of o -iodobenzyl alcohol with carbon monoxide under these conditions gave isobenzofuran-1(3 H )-one (phthalide).