Issue 5, 2020

A denitrogenative palladium-catalyzed cascade for regioselective synthesis of fluorenes

Abstract

We herein report a denitrogenative palladium-catalyzed cascade for the modular and regioselective synthesis of polysubstituted fluorenes. Hydrazone facilitates the Pd(II) to Pd(IV) oxidative addition in a Catellani pathway and is also the methylene synthon in the proposed reaction. Aryl iodides and 2-bromoarylaldehyde hydrazones undergo a norbornene-controlled tandem reaction sequence to give a broad scope of fluorenes in the presence of a palladium catalyst. The method described is scalable and adaptable to a three-component reaction with in situ generation of the hydrazone group. Preliminary mechanistic investigations have been conducted.

Graphical abstract: A denitrogenative palladium-catalyzed cascade for regioselective synthesis of fluorenes

Supplementary files

Article information

Article type
Edge Article
Submitted
14 Aug 2019
Accepted
17 Dec 2019
First published
17 Dec 2019
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY-NC license

Chem. Sci., 2020,11, 1411-1417

A denitrogenative palladium-catalyzed cascade for regioselective synthesis of fluorenes

W. C. Fu and F. Y. Kwong, Chem. Sci., 2020, 11, 1411 DOI: 10.1039/C9SC04062E

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