Carbonylative Cyclization of o-Halobenzoic Acids for Synthesis of N-Substituted Phthalimides Using Polymer-Supported Palladium–N-Heterocyclic 
Carbene as an Efficient, Heterogeneous, and Reusable Catalyst

Mayur V. Khedkar; Shoeb R. Khan; Kishor P. Dhake; Bhalchandra M. Bhanage

doi:10.1055/s-0032-1316565

Synthesis, Table of Contents

Synthesis 2012; 44(16): 2623-2629
DOI: 10.1055/s-0032-1316565

paper

Carbonylative Cyclization of o-Halobenzoic Acids for Synthesis of N-Substituted Phthalimides Using Polymer-Supported Palladium–N-Heterocyclic Carbene as an Efficient, Heterogeneous, and Reusable Catalyst

Mayur V. Khedkar

Department of Chemistry, Institute of Chemical Technology, N. Parekh Marg, Matunga, Mumbai 400 019, India, Fax: +91(22)33611020 Email: bm.bhanage@gmail.com Email: bm.bhanage@ictmumbai.edu.in

,

Shoeb R. Khan

Department of Chemistry, Institute of Chemical Technology, N. Parekh Marg, Matunga, Mumbai 400 019, India, Fax: +91(22)33611020 Email: bm.bhanage@gmail.com Email: bm.bhanage@ictmumbai.edu.in

,

Kishor P. Dhake

Department of Chemistry, Institute of Chemical Technology, N. Parekh Marg, Matunga, Mumbai 400 019, India, Fax: +91(22)33611020 Email: bm.bhanage@gmail.com Email: bm.bhanage@ictmumbai.edu.in

,

Bhalchandra M. Bhanage*

Department of Chemistry, Institute of Chemical Technology, N. Parekh Marg, Matunga, Mumbai 400 019, India, Fax: +91(22)33611020 Email: bm.bhanage@gmail.com Email: bm.bhanage@ictmumbai.edu.in

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Abstract

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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 1H-isoindole-1,3(2H)-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 1H-isoindole-1,3(2H)-diones, but with lower yields. Cyclization of o-iodobenzyl alcohol with carbon monoxide under these conditions gave isobenzofuran-1(3H)-one (phthalide).

Key words

carbonylative cyclization - heterogeneous catalysis - N-heterocyclic carbene - phosphine-free - phthalimides - isoindoles

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References

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