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- Title
Palladium(II)-Catalyzed Synthesis of Sulfinates from Boronic Acids and DABSO: A Redox-Neutral, Phosphine-Free Transformation.
- Authors
Deeming, Alex S.; Russell, Claire J.; Willis, Michael C.
- Abstract
A redox-neutral palladium(II)-catalyzed conversion of aryl, heteroaryl, and alkenyl boronic acids into sulfinate intermediates, and onwards to sulfones and sulfonamides, has been realized. A simple Pd(OAc)2 catalyst, in combination with the sulfur dioxide surrogate 1,4-diazabicyclo[2.2.2]octane bis(sulfur dioxide) (DABSO), is sufficient to achieve rapid and high-yielding conversion of the boronic acids into the corresponding sulfinates. Addition of C- or N-based electrophiles then allows conversion into sulfones and sulfonamides, respectively, in a one-pot, two-step process.
- Subjects
PALLADIUM oxides; AROMATIC compounds; ELECTROPHILES; SULFINATES; BORONIC acids
- Publication
Angewandte Chemie, 2016, Vol 128, Issue 2, p757
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.201508370