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Copper-catalyzed aerobic oxidation and cleavage/formation of C-S bond: a novel synthesis of aryl methyl sulfones from aryl halides and DMSO.

Chemical communications (Cambridge, England) (2012-06-26)
Gaoqing Yuan, Junhua Zheng, Xiaofang Gao, Xianwei Li, Liangbin Huang, Huoji Chen, Huanfeng Jiang
ABSTRACT

With atmospheric oxygen as the oxidant, a novel copper(I)-catalyzed synthesis of aryl methyl sulfones from aryl halides and widely available DMSO is described. The procedure tolerates aryl halides with various functional groups (such as methoxy, acetyl, chloro, fluoro and nitro groups), which could afford aryl methyl sulfones in moderate to high yields. The copper-catalyzed aerobic oxidation and the cleavage/formation of C-S bond are the key steps for this transformation.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Dimethyl sulfone, 98%
Supelco
Dimethyl sulfone, Standard for quantitative NMR, TraceCERT®