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

…, RF Langler, RT Baker, A Decken, SA Westcott

Index: Harrison, Daniel J.; Tam, Nga Chiu; Vogels, Christopher M.; Langler, Richard F.; Baker, R. Thomas; Decken, Andreas; Westcott, Stephen A. Tetrahedron Letters, 2004 , vol. 45, # 46 p. 8493 - 8496

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Citation Number: 41

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 ...