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Issue 31, 2016
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Why does Togni's reagent I exist in the high-energy hypervalent iodine form? Re-evaluation of benziodoxole based hypervalent iodine reagents

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Abstract

Togni's reagents have become very popular trifluoromethylating reagents in organic synthesis. The existing form of Togni's reagent I is a hypervalent iodine compound which lies much higher in energy than its ether isomer. The high-energy hypervalent iodine form makes Togni's reagent I very effective and versatile. The energy differences between the two forms correlate with the trans influence of the substituents. The five-membered ring in the benziodoxole-based scaffold is an important reason for its existence in the higher-energy form. The relation to Buchwald's 2014 research is discussed.

Graphical abstract: Why does Togni's reagent I exist in the high-energy hypervalent iodine form? Re-evaluation of benziodoxole based hypervalent iodine reagents

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Supplementary files

Article information


Submitted
15 Jan 2016
Accepted
25 Feb 2016
First published
26 Feb 2016

Chem. Commun., 2016,52, 5371-5374
Article type
Communication

Why does Togni's reagent I exist in the high-energy hypervalent iodine form? Re-evaluation of benziodoxole based hypervalent iodine reagents

T. Sun, X. Wang, H. Geng, Y. Xie, Y. Wu, X. Zhang and H. F. Schaefer III, Chem. Commun., 2016, 52, 5371
DOI: 10.1039/C6CC00384B

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