A four-component reaction to access 3,3-disubstituted indolines via the palladium-norbornene-catalyzed ortho amination/ipso conjunctive coupling.
Chem Sci
; 15(4): 1318-1323, 2024 Jan 24.
Article
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| MEDLINE
| ID: mdl-38274074
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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MEDLINE
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En
Ano de publicação:
2024
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Article