A four-component reaction to access 3,3-disubstituted indolines via the palladium–norbornene-catalyzed ortho amination/ipso conjunctive coupling
Literature Information
Publication Date
2023-12-14
DOI
10.1039/D3SC06409C
Impact Factor
9.825
Authors
Alexander J. Rago, Rong Ye, Xin Liu, Guangbin Dong
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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.
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Source Journal
Chemical Science
CiteScore:
14.4
Self-citation Rate:
3.9%
Articles per Year:
1413
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