Regioselectivity for the Rh(I)-catalyzed annulation of 1,2,3-thiadiazoles with alkynes: Experimental and Computational Analysis Reveal the Surprising Role of the Alkyne Substituent

Tasiana Reza, Marina A. Tokareva, Natalie K. Dobson, Alexandra L. Shanahan, Kyle Sheather, Christopher Richardson, Sinead T. Keaveney*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

2 Citations (Scopus)
2 Downloads (Pure)

Abstract

The Rh(I)-catalyzed denitrogenative annulation reactions of 1,2,3-thiadiazoles are a new direct approach to synthesizing densely functionalized heterocycles. The synthesis of multisubstituted thiophenes is possible using this methodology, however the difficulty to predict which regioisomer will form is a current limitation. In this current work, systematic computational and experimental studies were performed addressing how the terminal alkyne substituent effects regioselectivity. The data revealed that the electronic and steric properties of the alkyne substituent effects regioselectivity, including whether the group is aryl or alkyl. The insight gained from this study has allowed the development of a framework for predicting regioselectivity for the Rh(I)-catalyzed denitrogenative transannulation of 1,2,3-thiadiazoles with terminal alkynes.

Original languageEnglish
Article numbere202301117
Pages (from-to)1-8
Number of pages8
JournalChemCatChem
Volume15
Issue number24
Early online date20 Nov 2023
DOIs
Publication statusPublished - 19 Dec 2023

Bibliographical note

Copyright the Author(s) 2023. Version archived for private and non-commercial use with the permission of the author/s and according to publisher conditions. For further rights please contact the publisher.

Keywords

  • 1,2,3-thiadiazole
  • denitrogenation
  • mechanism
  • regioselectivity
  • thiophene

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