Issue 4, 2024
From the journal:

Chemical Science

A four-component reaction to access 3,3-disubstituted indolines via the palladium–norbornene-catalyzed ortho amination/ipso conjunctive coupling†

Alexander J. Rago, ORCID logo ‡a   Rong Ye,‡a   Xin Liu*a  and  Guangbin Dong ORCID logo *a  

* Corresponding authors

a Department of Chemistry, University of Chicago, Chicago, Illinois 60637, USA
E-mail: liuxin@uchicago.edu, gbdong@uchicago.edu

Abstract

As an important class of multicomponent reactions, the palladium/norbornene (Pd/NBE) cooperative catalysis has been mainly restricted to the coupling of an aryl halide, an electrophile and a nucleophile. Here, we report the development of a Pd/NBE-catalyzed four-component reaction, which involves ortho C–H amination/ipso conjunctive coupling using an alkene and an external nucleophile. The use of alkene-tethered nitrogen electrophiles provides a rapid and modular synthesis of 3,3-disubstituted indolines from readily available aryl iodides. The reaction exhibits broad functional group tolerance, and its utility is exemplified in a streamlined formal synthesis of a rhodamine dye. Preliminary results of the asymmetric version of this reaction have also been obtained.

Graphical abstract: A four-component reaction to access 3,3-disubstituted indolines via the palladium–norbornene-catalyzed ortho amination/ipso conjunctive coupling

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Article information

DOI
https://doi.org/10.1039/D3SC06409C
Article type
Edge Article
Submitted
29 Nov 2023
Accepted
14 Dec 2023
First published
14 Dec 2023
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., 2024,15, 1318-1323

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A four-component reaction to access 3,3-disubstituted indolines via the palladium–norbornene-catalyzed ortho amination/ipso conjunctive coupling

A. J. Rago, R. Ye, X. Liu and G. Dong, Chem. Sci., 2024, 15, 1318 DOI: 10.1039/D3SC06409C

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