Palladium-catalyzed selenoacylation of allenes leading to the regioselective formation of functionalized allyl selenides

Organic Letters
Masashi ToyofukuNobuaki Kambe

Abstract

Palladium-catalyzed regio- and stereoselective selenoacylation of allenes with selenol esters proceeded to produce functionalized allyl selenides with the acyl moiety at the inner carbon and the SePh group at the terminal carbon in high yields. A mechanism accounting for the observed regio- and stereoselectivities is proposed based on the results of DFT calculations.

References

Jul 18, 2001·Journal of the American Chemical Society·R HuaM Tanaka
Sep 26, 2002·Chemical Communications : Chem Comm·Eiji ShirakawaTamejiro Hiyama
Oct 11, 2003·Organic Letters·Takayoshi HiraiNobuaki Kambe
Apr 24, 2004·Organic & Biomolecular Chemistry·T Campbell BourlandAlexandre F T Yokochi
Jul 14, 2005·Chemical Reviews·Shengming Ma
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Mar 11, 2006·The Journal of Organic Chemistry·Uli KazmaierManuela Klein
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Jul 16, 2008·Chemical Communications : Chem Comm·Shelli R Waetzig, Jon A Tunge

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Citations

May 23, 2009·Chemical Communications : Chem Comm·Yasunori MinamiNobuaki Kambe
Feb 21, 2014·Chemical Society Reviews·Elena Soriano, Israel Fernández
Nov 28, 2017·Chemistry : a European Journal·Vera HirschbeckIvana Fleischer
Mar 1, 2013·Organic & Biomolecular Chemistry·Vutukuri Prakash ReddyNobuaki Kambe
Mar 10, 2011·Journal of Computational Chemistry·Meiyan WangZhijian Wu

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