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Synlett 2021; 32(09): 935-939
DOI: 10.1055/a-1373-7017
DOI: 10.1055/a-1373-7017
letter
Silyl Cyanopalladate-Catalyzed Friedel–Crafts-Type Cyclization Affording 3-Aryloxindole Derivatives
This work was supported by Grants-in-Aid from the Japan Society for the Promotion of Sciences (JSPS) (Nos. 19H02706 and 19K15548). T.Y. also acknowledges support from the Feasibility Study Program of the Frontier Chemistry Center, Faculty of Engineering, Hokkaido University.
Abstract
3-Aryloxindole derivatives were synthesized through a Friedel–Crafts-type cyclization. The reaction was catalyzed by a trimethylsilyl tricyanopalladate complex generated in situ from trimethylsilyl cyanide and Pd(OAc)2. Wide varieties of diethyl phosphates derived from N-arylmandelamides were converted almost quantitatively into oxindoles. When N,N-dibenzylamide was used instead of an anilide substrate, a benzo-fused δ-lactam was obtained. An oxindole product was subjected to substitution reactions to afford 3,3-diaryloxindoles with two different aryl groups.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-1373-7017.
- Supporting Information
Publication History
Received: 24 December 2020
Accepted after revision: 26 January 2021
Accepted Manuscript online:
26 January 2021
Article published online:
10 February 2021
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Under the photoirradiation conditions, the SRN1-reaction of o-chloroanilides affords the 3-aryloxindole derivatives, see: