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

Literature Information

Publication Date 2018-05-23
DOI 10.1039/C8OB00616D
Impact Factor 3.876
Authors

Pradeep Kumar Reddy Panyam, Ramdas Sreedharan, Thirumanavelan Gandhi


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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.

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Organic & Biomolecular Chemistry

Organic & Biomolecular Chemistry
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