Palladium-Catalyzed Direct C-2 Arylation of Indoles with Aryl Halides in Aqueous Medium

Guo-ping Lu; Chun Cai

doi:10.1055/s-0032-1317702

Synlett, Table of Contents

Synlett 2012; 23(20): 2992-2996
DOI: 10.1055/s-0032-1317702

letter

Palladium-Catalyzed Direct C-2 Arylation of Indoles with Aryl Halides in Aqueous Medium

Guo-ping Lu

Chemical Engineering College, Nanjing University of Science & Technology, Nanjing, Jiangsu 210094, P. R. of China Fax: +86(25)84315030 Email: c.cai@mail.njust.edu.cn

,

Chun Cai*

Chemical Engineering College, Nanjing University of Science & Technology, Nanjing, Jiangsu 210094, P. R. of China Fax: +86(25)84315030 Email: c.cai@mail.njust.edu.cn

› Author Affiliations

Abstract

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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.

Key words

arylation - indole - aqueous medium - green chemistry - synthetic method

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References and Notes

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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.

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