Issue 10, 2020

MOFs come up to scratch: an environmentally benign route to oxidative [4 + 2] cycloaddition on maleimides solely via MOFs in water

Abstract

The first Diels–Alder reaction of vinyl arenes with ene systems catalyzed by MOFs is reported. Maleimides and maleic anhydride were annulated/dehydrogenated on styrenes in the presence of a mixed-metal (FeNi)MIL-88A catalyst. Neither an additional oxidant nor a source of halogen is needed to drive this oxidative [4 + 2] cyclization reaction. Kinetic evidence such as activation entropy corroborates the proposed concerted mechanism. The reaction proceeds merely through a cost-effective catalyst in water as the greenest solvent. The product of annulation of styrene with maleic anhydride was used for the first L-selective annulative π-extension on naphthalene.

Graphical abstract: MOFs come up to scratch: an environmentally benign route to oxidative [4 + 2] cycloaddition on maleimides solely via MOFs in water

Supplementary files

Article information

Article type
Paper
Submitted
20 Feb 2020
Accepted
23 Apr 2020
First published
23 Apr 2020

Green Chem., 2020,22, 3216-3228

MOFs come up to scratch: an environmentally benign route to oxidative [4 + 2] cycloaddition on maleimides solely via MOFs in water

M. Abbasnia, M. Sheykhan, M. Bahmani and P. Taghizadeh, Green Chem., 2020, 22, 3216 DOI: 10.1039/D0GC00619J

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