Light-driven catalyst-free access to phthalazines: Merging two metal-free domino reactions in one-pot

17 January 2022, Version 1
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

We report the development of an unprecedented metal-free four-step one-pot synthetic strategy to access high-value functionalized phthalazines using o-methyl benzophenones as starting compounds. Combination of a light-mediated enolization of o-methyl benzophenones/Diels-Alder reaction domino process with a subsequent deprotection/aromatization domino reaction in one-pot leads to sustainable and efficient organic synthesis. The tangible advantages, i.e. absence of catalysts or additives, utilization of commercially available and/or easily accessible substrates, mild reaction conditions, simplicity, and single work-up procedure, make this combined process highly appealing for the direct construction of various 1-aryl-phthalazines.

Keywords

light-driven domino reaction
photoenolization
Diels-Alder reaction
one-pot reaction
phthalazines

Supplementary materials

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Description
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Supporting Information
Description
Supplementary Experimental Procedures; Analytical and Spectroscopic Data; Substrate Synthesis; General Procedure for the One-Pot Synthesis of Substituted Phthalazines; Supplementary 1H-, 13C-, and 19F-NMR Spectra
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