Journal
ACS CATALYSIS
Volume 9, Issue 12, Pages 10668-10673Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acscatal.9b04363
Keywords
nickel; catalysis; sulfinates; boronic acids; sulfones; sulfonamides; sulfonyl fluorides; sulfur dioxide
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Funding
- EPSRC [EP/K024205/1]
- EPSRC [EP/K024205/1] Funding Source: UKRI
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We report a redox-neutral Ni(II)-catalyzed sulfination of readily available aryl and heteroaryl boronic acids. Using the combination of commercially available, airstable NiBr2 center dot(glyme), a commercially available phenanthroline ligand, and DABSO, boronic acids are efficiently converted to the corresponding sulfinate salts, which can be further elaborated to valuable sulfonyl-containing groups, including sulfones, sulfonamides, sulfonyl fluorides, and sulfonate esters. The catalyst loading can be reduced to 2.5 mol % on a gram scale. This practically simple protocol tolerates an unprecedented range of pharmaceutically relevant and electron-poor (hetero)aryl boronic acids, allowing the direct synthesis of active pharmaceutical ingredients.
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