Stereoselective intermolecular allylic C-H trifluoroacetoxylation of functionalized alkenes

Journal of the American Chemical Society
Rauful AlamKálmán J Szabó

Abstract

Pd-catalyzed allylic C-H trifluoroacetoxylation of substituted alkenes was performed using PhI(OCOCF(3))(2) as the oxidant and acyloxy source. Trifluoroacetoxylation of monosubstituted cyclopentenes and cyclohexenes proceeds with excellent regio- and diastereoselectivity. Studies with one of the possible (η(3)-allyl)Pd(II) intermediates suggest that the reaction proceeds via stereoselective formation of Pd(IV) intermediates and subsequent stereo- and regioselective reductive elimination of the product.

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Citations

Jul 17, 2013·Journal of the American Chemical Society·Iulia I Strambeanu, M Christina White
Nov 21, 2012·Organic Letters·Matthew G LauerJames P Stambuli
May 13, 2017·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Felipe Cesar Sousa E SilvaSarah E Wengryniuk
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May 1, 2015·Organic & Biomolecular Chemistry·Haidong Gu, Congyang Wang
Nov 3, 2020·Frontiers in Chemistry·Samata E Shetgaonkar, Fateh V Singh
Aug 27, 2014·Journal of the American Chemical Society·Nicole M CamassoMelanie S Sanford
Feb 14, 2015·Journal of the American Chemical Society·Jiashun ChengGuosheng Liu
Dec 1, 2017·Organic Letters·Lujia MaoTodd B Marder
Jan 6, 2018·Journal of the American Chemical Society·Chaohuang ChenGuosheng Liu
Jun 12, 2019·Journal of the American Chemical Society·Jonathan N JaworskiShannon S Stahl
Jan 21, 2020·The Journal of Organic Chemistry·Sk Sheriff ShahN D Pradeep Singh

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