Synthesis of polysubstituted iodobenzene derivatives from alkynylsilanes and 1,3-dienes via diels-alder/oxidation/iodination reaction sequence

Organic Letters
Robert Möckel, Gerhard Hilt

Abstract

The cobalt-catalyzed Diels-Alder reaction of trimethylsilyl-substituted alkynes with 1,3-dienes led to dihydroaromatic intermediates which were transformed into iodobenzene derivatives. For this transformation, the dihydroaromatic intermediates had to be oxidized and the trimethylsilyl-substituted arene had to undergo a silicon-iodine exchange reaction. For this purpose, a number of oxidizing agents and iodonium sources were tested in order to realize the desired two transformations in a single step. Eventually, the combination of tert-butyl hydroperoxide (TBHP), zinc iodide, and potassium carbonate led to the desired oxidation/iodination in good to excellent yields in a short reaction time at ambient temperatures.

References

Nov 25, 2003·Organic Letters·Raúl Montoro, Thomas Wirth
Mar 11, 2004·Chemical Reviews·Steven T Diver, Anthony J Giessert
Aug 24, 2006·Angewandte Chemie·Gerhard HiltWilfried Hess
Jun 19, 2008·Journal of the American Chemical Society·Philipp MörschelGernot Frenking
Jul 9, 2009·Organic Letters·Gerhard HiltJonas Treutwein
Apr 14, 2011·Organic Letters·Ling ZhouYing-Yeung Yeung
May 3, 2014·The Journal of Organic Chemistry·Andivelu Ilangovan, Gandhesiri Satish
May 16, 2014·Chemistry : a European Journal·Christiane E I KnappkeAxel Jacobi von Wangelin
Jun 4, 2014·Chemical Record : an Official Publication of the Chemical Society of Japan ... [et Al.]·Gerhard Hilt
Jun 7, 2014·Chemistry : a European Journal·Toni MoragasRuben Martin

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Citations

Dec 28, 2016·Journal of the American Chemical Society·Anton A ToutovRobert H Grubbs
Dec 8, 2017·Angewandte Chemie·Robert MöckelGerhard Hilt
Feb 6, 2019·Chemistry : a European Journal·Maren Wissing, Armido Studer

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