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DOI: 10.1055/s-0029-1219921
Indium(I)-Mediated Radical Carbon-Carbon Bond-Forming Reaction in Aqueous Media
Publikationsverlauf
Publikationsdatum:
06. Mai 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
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References and Notes
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]
.