A gentle and efficient route for the deoxygenation of sulfoxides using catecholborane (HBcat; cat = 1,2-O 2C 6H 4)

The addition of catecholborane (HBcat; cat = 1,2-O 2C 6H 4) to a wide range of sulfoxides affords the corresponding sulfides, dihydrogen, and catBOBcat. The addition of catecholborane (HBcat; cat = 1,2-O 2C 6H 4) to a wide range of sulfoxides affords the corresponding sulfides, dihydrogen, and catBO...

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Bibliographic Details
Published in:Tetrahedron letters 2004-11, Vol.45 (46), p.8493-8496
Main Authors: Harrison, Daniel J., Tam, Nga Chiu, Vogels, Christopher M., Langler, Richard F., Baker, R. Thomas, Decken, Andreas, Westcott, Stephen A.
Format: Article
Language:English
Subjects:
Catalysis
Catecholborane
Deoxygenation
Lewis acid
Sulfoxides
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Summary:The addition of catecholborane (HBcat; cat = 1,2-O 2C 6H 4) to a wide range of sulfoxides affords the corresponding sulfides, dihydrogen, and catBOBcat. The addition of catecholborane (HBcat; cat = 1,2-O 2C 6H 4) 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.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2004.09.068