Hypervalent Iodine-Based Activation of Triphenylphosphine for the Functionalization of Alcohols

Abstract The use of hypervalent iodine reagents as a general tool for the activation of PPh 3 and its application to the functionalization of alcohols is reported. Combination of PPh 3 with PhICl 2 or TolIF 2 gives dihalophosphoranes that are characterized by 31 P NMR, however, with PhIOAc 2 , PhI(O...

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Bibliographic Details
Published in:Synlett 2017-12, Vol.28 (20), p.2871-2875
Main Authors: Eljo, Jasmin, Carle, Myriam S., Murphy, Graham K.
Format: Article
Language:English
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Summary:Abstract The use of hypervalent iodine reagents as a general tool for the activation of PPh 3 and its application to the functionalization of alcohols is reported. Combination of PPh 3 with PhICl 2 or TolIF 2 gives dihalophosphoranes that are characterized by 31 P NMR, however, with PhIOAc 2 , PhI(OTFA) 2 , or the cyclic chloro(benzoyloxy)iodane, no phosphoranes were observed. Reaction of these iodanes with PPh 3 in the presence of primary, secondary, or tertiary alcohols results in either halogenation or acyl-transfer products in moderate to high yield.
ISSN:0936-5214
1437-2096
DOI:10.1055/s-0036-1589069