Issue 23, 2018

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

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

Supplementary files

Article information

Article type
Paper
Submitted
12 Mar 2018
Accepted
22 May 2018
First published
23 May 2018

Org. Biomol. Chem., 2018,16, 4357-4364

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

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements