Metal-Free Desulfonylation Reaction Through Visible-Light Photoredox Catalysis

The desulfonylation of β‐arylketosulfones has been achieved in good to excellent yields by using 3‐W blue LEDs light, 1 mol‐% organic dye eosin Y bis(tetrabutylammonium salt) as photocatalyst, and diisopropylethylamine as reducing agent. Mechanistic studies demonstrate that oxidative quenching of th...

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Bibliographic Details
Published in:European journal of organic chemistry 2013-11, Vol.2013 (33), p.7528-7532
Main Authors: Yang, Deng-Tao, Meng, Qing-Yuan, Zhong, Jian-Ji, Xiang, Ming, Liu, Qiang, Wu, Li-Zhu
Format: Article
Language:English
Subjects:
Beta
Dyes/pigments
Photocatalysis
Photochemistry
Sulfur
Synthetic methods
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Summary:The desulfonylation of β‐arylketosulfones has been achieved in good to excellent yields by using 3‐W blue LEDs light, 1 mol‐% organic dye eosin Y bis(tetrabutylammonium salt) as photocatalyst, and diisopropylethylamine as reducing agent. Mechanistic studies demonstrate that oxidative quenching of the excited eosin Y by β‐arylketosulfones plays a crucial role in the present photoredox catalytic cycle. Reductive desulfonylation is essential to enable to use of a sulfone as an auxiliary group. For reductive removal of sulfones, highly aggressive metal‐containing reducing agents and harsh reaction conditions are often employed. In this paper, metal‐free desulfonylation of β‐arylketosulfones can be achieved efficiently at room temperature under visible‐light irradiation.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.201301105