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Diprotonative stabilization of ring-opened carbocationic intermediates: conversion of tetrahydroisoquinoline to triarylmethanes

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Abstract

Superacid-promoted conversion of tetrahydroisoquinolines to triarylmethanes via tandem reactions of C–N bond scission, Friedel–Crafts alkylation, C–O bond scission, and electrophilic aromatic amidation was developed. Dication formation was important for stabilizing the ring-opened carbocationic intermediate, which is a new role for diprotonation in reaction mechanisms.

Graphical abstract: Diprotonative stabilization of ring-opened carbocationic intermediates: conversion of tetrahydroisoquinoline to triarylmethanes

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Article information


Submitted
16 Mar 2020
Accepted
17 Jun 2020
First published
18 Jun 2020

Chem. Commun., 2020, Advance Article
Article type
Communication

Diprotonative stabilization of ring-opened carbocationic intermediates: conversion of tetrahydroisoquinoline to triarylmethanes

H. Kurouchi, Chem. Commun., 2020, Advance Article , DOI: 10.1039/D0CC01969K

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