期刊
CHEMISTRY-A EUROPEAN JOURNAL
卷 15, 期 39, 页码 10225-10232出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.200900942
关键词
homolytic substitution; radical reactions; sulfinamides; sulfinates; sulfur heterocycles
资金
- UPMC
- CNRS IUF
- ANR [BLAN0309]
- Region Ile-de-France Technical assistance
A general and efficient method for the synthesis of cyclic sulfinates and sulfinamides based on intramolecular homolytic substitution (S(H)1) at the sulfur atom by aryl or alkyl radicals is described. Both alkyl and benzofused compounds call be accessed directly from easily prepared acyclic precursors. Enantiomerically enriched sulfur-based heterocycles were formed through an S(H)i process with inversion of configuration at the sulfur atom cyclization of prochiral radicals proceeded with varying stereochemical outcomes, depending on the sire of the incoming radical 2-Pyridyl and 2-quinolyl radicals led to biaryl compounds, which result from attack onto the ortho position of the arylsulfinate rather than a thiophilic substitution.
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