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Synlett 2010(9): 1341-1344  
DOI: 10.1055/s-0029-1219921
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Indium(I)-Mediated Radical Carbon-Carbon Bond-Forming Reaction in Aqueous Media

Masafumi Uedaa, Hideto Miyabeb, Masafumi Toriia, Takahiro Kimuraa, Okiko Miyata*a, Takeaki Naito*a
a Kobe Pharmaceutical University, Motoyamakita, Higashinada, Kobe 658-8558, Japan
Fax: +81(78)4417554; Fax: +81(78)4417642; e-Mail: miyata@kobepharma-u.ac.jp; e-Mail: taknaito@kobepharma-u.ac.jp;
b School of Pharmacy, Hyogo University of Health Sciences, Minatojima, Chuo-ku, Kobe 650-8530, Japan
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Publication History

Received 12 March 2010
Publication Date:
06 May 2010 (online)

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Abstract

The carbon-carbon bond-forming radical reactions using indium(I) chloride and copper(I) chloride proceeded effectively through a single-electron transfer process in aqueous media.

Key words

indium(I) chloride - copper(I) chloride - radical addition - oxime ether - domino reaction - aqueous media

13

General Procedure for the Reaction of Oxime Ether 1
To a microtube containing oxime ether 1 (50 mg, 0.26 mmol), i-PrI (1.3 mL, 1.3 mmol), indium salt (2.6 mmol), copper salt (0.26 mmol), and MeOH (0.2 mL) H2O was added dropwise (0.4 mL) at r.t. After the reaction mixture was vigorously stirred at the same temperature for 1 h, i-PrI (1.3 mL, 1.3 mmol) was added to the reaction mixture. After being vigorously stirred at the same temperature for 1 h, the reaction mixture was diluted with aq 36% potassium sodium (+)-tartrate and then extracted with EtOAc. The organic phase was dried over MgSO4 and concentrated under reduced pressure. Purification of the residue by preparative TLC (hexane-EtOAc, 4:1) afforded the adduct 2 4b in the yields shown in Table  [¹] .