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Issue 10, 2020
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MOFs come up to scratch: an environmentally benign route to oxidative [4 + 2] cycloaddition on maleimides solely via MOFs in water

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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

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Article information


Submitted
20 Feb 2020
Accepted
23 Apr 2020
First published
23 Apr 2020

Green Chem., 2020,22, 3216-3228
Article type
Paper

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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