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Synlett 2012; 23(20): 2992-2996
DOI: 10.1055/s-0032-1317702
DOI: 10.1055/s-0032-1317702
letter
Palladium-Catalyzed Direct C-2 Arylation of Indoles with Aryl Halides in Aqueous Medium
Further Information
Publication History
Received: 13 October 2012
Accepted after revision: 05 November 2012
Publication Date:
28 November 2012 (online)
Abstract
A newly developed, efficient catalytic system for direct C2-arylation of indoles with aryl halides in aqueous medium under mild conditions (80 °C) is reported. These procedures are free of toxic solvents, and exhibit improved yields and high chemo- and regioselectivity.
Supporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synlett.
- Supporting Information
-
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- 15 General Procedure for Direct C-2 Arylation of Indoles in Aqueous Medium: Pd(Amphos)2Cl2 (0.005 mmol), NaOH (0.375 mmol), tetrachlorophthalic anhydride (TCPA; 0.375 mmol) and indole 1 (0.250 mmol) were weighed into a microwave vial at r.t. Aryl halide (0.375 mmol), EtOH (0.10 mL) and H2O (0.50 mL) were then added by syringe. The resulting solution was allowed to stir at 80 °C for 24 h. Upon completion, the reaction mixture was diluted with EtOAc (4.0 mL), filtered through a bed of silica gel layered over Celite, The volatiles were removed in vacuo to afford the crude product. The extent of conversion was determined by GC–MS. Further column chromatography on silica gel afforded the pure desired product 2.