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A gentle and efficient route for the deoxygenation of sulfoxides using catecholborane (HBcat; cat = 1,2-O2C6H4) |
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| Authors: | Daniel J Harrison Christopher M Vogels R Thomas Baker Andreas Decken |
| Institution: | a Department of Chemistry, Mount Allison University, Sackville, NB, Canada E4L 1G8 b Los Alamos Catalysis Initiative, Chemistry Division, MS J582, Los Alamos National Laboratory, Los Alamos, NM 87545, USA c Department of Chemistry, University of New Brunswick, Fredericton, NB, Canada E3B 5A3 |
| Abstract: | The addition of catecholborane (HBcat; cat = 1,2-O2C6H4) to a wide range of sulfoxides affords the corresponding sulfides, dihydrogen, and catBOBcat. The diboron compound catBOBcat acts like a Lewis acid and will coordinate one molecule of the starting sulfoxide. Although deoxygenations with bulky or electron withdrawing sulfoxides are slow, these reactions can be greatly accelerated with the use of excess HBcat or by employing a rhodium catalyst. |
| Keywords: | Catalysis Catecholborane Deoxygenation Lewis acid Sulfoxides |
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