Facile chemoselective dithioacetalization of carbonyl compounds promoted by Fe₃O₄@MCM-41-GPTMS-Gu-Cu^IINPs as an efficient magnetic nanostructured catalyst

Abstract

Dithioacetalization, as a well-known class of organic transformation, was carried out for protection of a wide variety of aromatic (with electron releasing and electron withdrawing substituents), heteroaromatic and aliphatic aldehydes as well as ketones by 1,2-ethanedithiol/or 1,3-propanedithiol in the presence of Fe₃O₄@MCM-41-GPTMS-Gu-Cu^IINPs. The corresponding 1,3-dithiolanes and 1,3-dithianes were obtained chemoselectively in the presence of Fe₃O₄@MCM-41-GPTMS-Gu-Cu^IINPs with hexagonal core-shell structure, superparamagnetic behavior, and average particle size of 8–25 nm under mild reaction conditions. The nanostructured catalyst could be separated easily from the reaction mixture using a magnetic bar and reused in several reaction runs without any remarkable reduction in its catalytic activity. Nearly neutral conditions, good to high yields of the products, operational simplicity, easy work-up procedure, compatibility with various functional groups make the present method valuable in addition to the known methodologies.

GRAPHICAL ABSTRACT

Keywords:

• Fe₃O₄@MCM-41-GPTMS-Gu-Cu^IINPs
• carbonyl compounds
• dithiolanes
• dithianes
• dithioacetalization
• nanostructured catalyst

Acknowledgments

The authors gratefully acknowledge the partial support of this study by Ferdowsi University of Mashhad Research Council (Grant No. p/3/56445).

Disclosure statement

No potential conflict of interest was reported by the authors.