Continuous-Flow Synthesis of Trimethylsilylphenyl Perfluorosulfonate Benzyne Precursors

Coumarin to Isocoumarin: One-Pot Synthesis of 3-Substituted Isocoumarins from 4-Hydroxycoumarins and Benzyne Precursors.

A novel transition-metal-free direct synthesis of 3-substituted isocoumarin from 4-hydroxycoumarin and a benzyne precursor is developed. This synthetic strategy proceeds via C-O and C-C bond cleavage as well as C-O and C-C bond formations in a single reaction vessel by simple treatment with CsF in the absence of catalyst. This methodology affords moderate to good yields of 3-substituted isocoum...

Synthesis of benzonorbornadienes: regioselective benzyne formation.

This report details the synthesis of several benzonorbornadienes by Diels--Alder cycloaddition of cyclopentadiene derivatives with substituted benzyne intermediates, which were generated by low-temperature metal--halogen exchange of halobenzenes. General conditions were developed, allowing synthesis of most benzonorbornadienes described herein at the multigram scale with isolated yields approac...

Continuous flow synthesis of conjugated polymers.

A selection of conjugated polymers, widely studied in organic electronics, was synthesised using continuous flow methodology. As a result of superior heat transfer and reagent control, excellent polymer molecular mass distributions were achieved in significantly reduced reaction times compared to conventional batch reactions.

Multistep Continuous-Flow Synthesis of (–)-Oseltamivir

A continuous-flow synthesis of (–)-oseltamivir composed of five flow units was accomplished. In each unit, the following reactions proceed efficiently: (1) a diphenylprolinol silyl ether mediated Michael reaction, (2) a domino reaction of Michael and intermolecular Horner– Wadsworth–Emmons reactions, (3) protonation, (4) epimerization, and (5) reduction of a nitro group to an amine. (–)-Oseltam...

Cu-catalysed pyrazole synthesis in continuous flow†