Ligand-Mediated and Copper-Catalyzed C(sp(3))-H Bond Functionalization of Aryl Ketones with Sodium Sulfinates under Mild Conditions.

Abstract:

:A novel and convenient copper (II) bromide and 1,8-diazabicyclo[5.4.1]undec-7-ene (DBU) or 1,10-phenanthroline catalysis protocol for the construction of α-alkyl-β-keto sulfones via C(sp(3))-H bond functionalization followed by C(sp(3))-S bond formation between aryl ketones and sodium sulfinates at room temperature has been developed. This method is applicable to a wide range of aryl ketones and sodium sulfinates. The electronic effects of aryl ketones and ligands effects of the copper salts are crucial for this transformation. Typically, substituted aryl ketones with electron-withdrawing group do not need any ligand to give a good to excellent yield, while substituted aryl ketones with electron-donating group and electron-rich heteroaromatic ketones offer a good to excellent yield only under the nitrogen-based ligands. The practical value of this transformation highlights the efficient and robust one-pot synthesis of α-alkyl-β-keto sulfones.

journal_name

Sci Rep

journal_title

Scientific reports

authors

Lan XW,Wang NX,Bai CB,Zhang W,Xing Y,Wen JL,Wang YJ,Li YH

doi

10.1038/srep18391

subject

Has Abstract

pub_date

2015-12-18 00:00:00

pages

18391

issn

2045-2322

pii

srep18391

journal_volume

5

pub_type

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