Synlett 2015; 26(18): 2593-2597
DOI: 10.1055/s-0035-1560575
letter
© Georg Thieme Verlag Stuttgart · New York

tert-Butoxide-Mediated Arylation of 1-Acetylindolin-3-ones with Diaryliodonium Salts

Yanxia Zhang
a   School of Chemical and Environmental Engineering, Shanghai Institute of Technology, 100 Haiquan Road, Shanghai 201418, P. R. of China   Email: zjliu@sit.edu.cn
b   Shanghai-Hong Kong Joint Laboratory in Chemical Synthesis, Shanghai Institute of Organic Chemistry, The Chinese Academy of Sciences, 345 Ling Ling Road, Shanghai 200032, P. R. of China   Email: jianweihan@sioc.ac.cn
,
Jianwei Han*
b   Shanghai-Hong Kong Joint Laboratory in Chemical Synthesis, Shanghai Institute of Organic Chemistry, The Chinese Academy of Sciences, 345 Ling Ling Road, Shanghai 200032, P. R. of China   Email: jianweihan@sioc.ac.cn
,
Zhen-Jiang Liu*
a   School of Chemical and Environmental Engineering, Shanghai Institute of Technology, 100 Haiquan Road, Shanghai 201418, P. R. of China   Email: zjliu@sit.edu.cn
› Author Affiliations
Further Information

Publication History

Received: 06 July 2015

Accepted after revision: 27 August 2015

Publication Date:
22 September 2015 (online)


Abstract

A procedure for the 2-arylations of indolinone derivatives with diaryliodonium salts mediated by potassium tert-butoxide is developed. Various monoarylated indolinone derivatives are readily obtained in 24–70% yield via this method. The alkylation of monoarylated indolinone derivatives with allyl bromide or benzyl bromide affords the corresponding 2,3-disubstituted products in 60% and 70% yield, respectively.

Supporting Information

 
  • References and Notes

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  • 12 Compounds 3ba−ja; General Procedure Indolinone 1 (0.2 mmol, 1 equiv) and t-BuOK (22.4 mg, 0.2 mmol, 1.0 equiv) were added to a Schlenk tube. THF (2 mL) was added using a syringe and the mixture was stirred for 15 min. Next, iodonium salt 2 (0.0860 g, 0.2 mmol, 1.0 equiv) was added and the mixture was stirred at 30 °C for 10 h. After cooling to r.t., the solvent was removed in vacuo and the residue was purified over silica gel (EtOAc–hexane) to afford the desired product. Analytical data for representative sample 3aa is provided below. 1-Acetyl-2-phenylindolin-3-one (3aa) Yield: 29.2 mg (58%); white solid; mp 125–128 °C. 1H NMR (300 MHz, CDCl3): δ = 8.67 (d, J = 7.8 Hz, 1 H), 7.80–7.65 (m, 2 H), 7.44–7.32 (m, 3 H), 7.30–7.22 (m, 3 H), 5.19 (s, 1 H), 2.05 (s, 3 H). 13C NMR (75 MHz, CDCl3): δ = 195.2, 169.5, 154.1, 137.8, 134.8, 129.7, 129.0, 126.0, 125.0, 123.0, 118.7, 107.9, 69.9, 24.8. HRMS (ESI): m/z [M + H]+ calcd for C16H13NO2: 252.1025; found: 252.1025.