Rhodium-Catalyzed Annulative Coupling of Isothiazoles with Alkynes through N-S Bond Cleavage.

Gen MiharaTeppei NoguchiYuji Nishii Yoshihiro HayashiSusumu KawauchiMasahiro Miura

Published in: Organic letters (2019)

A Rh(III)-catalyzed annulative coupling of 3,5-diarylisothiazoles and alkynes is reported. The N-S bond in the isothiazole ring acts as an internal oxidant to regenerate the Rh(III) species in combination with an external Cu(II) oxidant, and the corresponding 1:2 coupling products are obtained. The remarkable difference in the reaction outcome between isothiazoles and the relevant isoxazoles has been investigated by DFT calculations, revealing that the relative stability of the enolate intermediates dictates the product selectivity.

Keyphrases

room temperature
electron transfer
density functional theory
ionic liquid
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molecular dynamics simulations
molecular dynamics
molecular docking
high resolution
transition metal
dna binding
mass spectrometry
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