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Issue 35, 2018
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An umpolung of Lewis acidity/basicity at nitrogen by deprotonation of a cyclic (amino)(aryl)nitrenium cation

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Abstract

A cyclic (amino)(aryl)nitrenium cation 2 has been achieved by treatment of spiro[fluorene-9,3′-indazole] (1) with Ph2CHCl and AgBF4. This cation 2 is Lewis acidic at nitrenium N1, reacting with PMe3 affording a Lewis acid/base adduct 3. In contrast, deprotonation of 2 with other bases provides a neutral compound 4 which is Lewis basic at N1, reacting with electrophiles including GaCl3, MeOTf and PhNCO.

Graphical abstract: An umpolung of Lewis acidity/basicity at nitrogen by deprotonation of a cyclic (amino)(aryl)nitrenium cation

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Article information


Submitted
15 Feb 2018
Accepted
05 Mar 2018
First published
05 Mar 2018

Chem. Commun., 2018,54, 4390-4393
Article type
Communication

An umpolung of Lewis acidity/basicity at nitrogen by deprotonation of a cyclic (amino)(aryl)nitrenium cation

J. Zhou, L. L. Liu, L. L. Cao and D. W. Stephan, Chem. Commun., 2018, 54, 4390
DOI: 10.1039/C8CC01331D

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