期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 143, 期 38, 页码 15576-15581出版社
AMER CHEMICAL SOC
DOI: 10.1021/jacs.1c08052
关键词
-
资金
- EPSRC [EP/K024205/1]
This study presents a new redox-neutral Ni(II)-catalyzed reaction system for the addition of (hetero)aryl boroxines to N-sulfinyltritylamine to produce sulfinamide products. The initially formed sulfinamides can be further transformed into various compounds through chlorination and hydrolysis. These transformations can all be conducted through one-pot procedures.
We report a redox-neutral Ni(II)-catalyzed addition of (hetero)aryl boroxines to N-sulfinyltritylamine (TrNSO). The reactions use a catalyst generated from the combination of commercial, air-stable NiCl2 center dot(glyme) and a commercially available bipyridine ligand, and deliver sulfinamide products. The scope of the reaction is established using a sulfonimidamide synthesis, in which the initially formed sulfinamides undergo oxidative chlorination with the inexpensive and safe chlorinating agent, trichloroisocyanuric acid (TCCA), to produce sulfonimidoyl chlorides as key intermediates. These are combined in situ with a range of amines to deliver sulfonimidamides. The sulfonimidoyl chlorides can also be elaborated into primary sulfonamides via hydrolysis, and sulfonimidoyl fluorides via treatment with fluoride. These transformations are all achieved using one-pot procedures. Unprotected, primary sulfinamides are also available. For larger-scale reactions, the catalyst loading can be reduced to 1 mol %.
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