Scalable, Chemoselective Nickel Electrocatalytic Sulfinylation of Aryl Halides with SO2

Simple access to aryl sulfinates from aryl iodides and bromides is reported using an inexpensive Ni‐electrocatalytic protocol. The reaction exhibits a broad scope, uses stock solution of simple SO2 as sulfur source, and can be scaled up in batch and recycle flow settings. The limitations of this rea...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2022-09, Vol.61 (37), p.e202208080-n/a
Main Authors: Lou, Terry Shing‐Bong, Kawamata, Yu, Ewing, Tamara, Correa‐Otero, Guillermo A., Collins, Michael R., Baran, Phil S.
Format: Article
Language:English
Subjects:
Aromatic compounds
Bromides
Chemoselectivity
Electrochemistry
Fluoride
Halides
Iodides
Nickel
Sulfur
Sulfur dioxide
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Summary:Simple access to aryl sulfinates from aryl iodides and bromides is reported using an inexpensive Ni‐electrocatalytic protocol. The reaction exhibits a broad scope, uses stock solution of simple SO2 as sulfur source, and can be scaled up in batch and recycle flow settings. The limitations of this reaction are clearly shown and put into context by benchmarking with state‐of‐the‐art Pd‐based methods. Enabled by electrochemistry, the conversion of aryl halides to sulfinates using an inexpensive Ni catalyst at room temperature is reported. The use of SO2 stock solution at controlled concentration represents a convenient sulfur source. The sulfinate intermediates can be derivatized into sulfonyl fluorides, sulfonamide, and sulfone in a one‐pot fashion. This reaction exhibits a broad substrate scope and can be easily scaled up in batch and flow.
ISSN:1433-7851
1521-3773
1521-3773
DOI:10.1002/anie.202208080