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Issue 23, 2018
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Synthesis of topologically constrained naphthalimide appended palladium(II)–N-heterocyclic carbene complexes – insights into additive controlled product selectivity

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Abstract

Topologically constrained naphthalimide appended Pd–NHCs were synthesized and characterized. These structurally related complexes were catalytically compared with previously synthesized Pd–NHCs in the regioselective heteroannulation of o-haloanilines and arylethynyl-trimethylsilane. The unique effect of an additive on product selectivity has been clearly demonstrated. The scope of the reaction with respect to different TMS protected alkynes and o-haloanilines is presented. Importantly, the step-economical regioselective synthesis of N-alkyl-3-aryl-indoles from o-haloanilines and arylethynyl-trimethylsilane assisted by Pd(II)–NHCs has been clearly demonstrated via one-pot heteroannulation, TMS deprotection and N-alkylation. In addition, synthetic utility was demonstrated with several derivatizations.

Graphical abstract: Synthesis of topologically constrained naphthalimide appended palladium(ii)–N-heterocyclic carbene complexes – insights into additive controlled product selectivity

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Publication details

The article was received on 12 Mar 2018, accepted on 22 May 2018 and first published on 23 May 2018


Article type: Paper
DOI: 10.1039/C8OB00616D
Citation: Org. Biomol. Chem., 2018,16, 4357-4364
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    Synthesis of topologically constrained naphthalimide appended palladium(II)–N-heterocyclic carbene complexes – insights into additive controlled product selectivity

    P. K. R. Panyam, R. Sreedharan and T. Gandhi, Org. Biomol. Chem., 2018, 16, 4357
    DOI: 10.1039/C8OB00616D

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