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

Masafumi Ueda; Hideto Miyabe; Masafumi Torii; Takahiro Kimura; Okiko Miyata; Takeaki Naito

doi:10.1055/s-0029-1219921

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Synlett 2010(9): 1341-1344
DOI: 10.1055/s-0029-1219921

LETTER

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

Masafumi Ueda^a, Hideto Miyabe^b, Masafumi Torii^a, Takahiro Kimura^a, 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

Further Information

Publication History

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

Abstract
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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

References and Notes

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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] .