Journal
ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 16, Issue 23, Pages 4357-4364Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c8ob00616d
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Funding
- DST-SERB [EMR/2016/005461]
- Seed Grant, VIT University, Vellore
- CSIR-SRF [01(2815)/14/EMR-II]
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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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