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Issue 89, 2014
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Electrophilic iodine(i) compounds induced semipinacol rearrangement via C–X bond cleavage

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Abstract

Neutral electrophilic iodine(I) species proved to be efficient reagents for C–X bond cleavage of various cyclic and acyclic α-silyloxyhalides, and the induced desilylative semipinacol rearrangement provided the corresponding ketones in good yields. The reaction is operationally simple, and proceeds under mild conditions with good functional group compatibility. Mechanistic investigations, including computational studies, were also performed.

Graphical abstract: Electrophilic iodine(i) compounds induced semipinacol rearrangement via C–X bond cleavage

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Article information


Submitted
01 Aug 2014
Accepted
16 Sep 2014
First published
16 Sep 2014

Chem. Commun., 2014,50, 13691-13694
Article type
Communication
Author version available

Electrophilic iodine(I) compounds induced semipinacol rearrangement via C–X bond cleavage

N. Tsuji, Y. Kobayashi and Y. Takemoto, Chem. Commun., 2014, 50, 13691
DOI: 10.1039/C4CC06014H

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