Allylic oxidations of terminal olefins using a palladium thioether catalyst

Organic Letters
William H HendersonJames P Stambuli

Abstract

A palladium catalyst that converts terminal olefins to linear allylic acetates at lower catalyst loadings and faster reaction times than current systems is reported. This reaction can be conducted using benzoquinone as the oxidizing agent or catalytic amounts of copper and hydroquinone under one atmosphere of oxygen. Preliminary reactivity studies of pi-allylpalladium complexes under our reaction conditions do not provide results similar to those obtained in the catalytic reaction, which may suggest an alternative reaction pathway. The palladium catalyst is ligated by an aryloxyalkyl aryl sulfide, which is identified as a new ligand for homogeneous catalysis.

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Citations

Oct 18, 2011·Chemical Communications : Chem Comm·Huoji ChenHuanfeng Jiang
Dec 18, 2015·Organic Letters·Heng ZhangShang-Dong Yang
Feb 16, 2017·Chemical Communications : Chem Comm·Ana SirventMiguel Yus
Jun 18, 2017·Journal of the American Chemical Society·Bradley J GorslineBrad P Carrow
Aug 5, 2016·Organic & Biomolecular Chemistry·Ganesh MajjiBhisma K Patel
Aug 18, 2010·Dalton Transactions : an International Journal of Inorganic Chemistry·Christophe FliedelPierre Braunstein
Mar 7, 2019·Organic & Biomolecular Chemistry·Yunlong Guo, Zengming Shen
Jul 11, 2013·Chemistry : a European Journal·Chi Chip LeJames P Stambuli
Apr 16, 2014·Organic & Biomolecular Chemistry·Huoji ChenHuanfeng Jiang
Feb 17, 2015·Chemical Science·Hasnain A MalikAndrew W Patterson
Aug 7, 2019·Organic & Biomolecular Chemistry·Dilna B Sreedhar, Raghavan B Sunoj
Jan 9, 2013·Chemical Communications : Chem Comm·Dan YangKang Zhao
Jan 20, 2021·The Journal of Organic Chemistry·Timothy J ParisRachel Willand-Charnley
Apr 19, 2017·Bioorganic & Medicinal Chemistry·Bumki KimJiyong Hong
Dec 29, 2020·Angewandte Chemie·Jie LiuJan-E Bäckvall
May 14, 2021·The Journal of Organic Chemistry·Andrea ZanettiJanine Cossy
Jul 29, 2010·Journal of the American Chemical Society·Nicolaas A VermeulenM Christina White
Jan 1, 2014·Journal of the American Chemical Society·Urs GellrichBernhard Breit
Oct 21, 2011·Journal of the American Chemical Society·Christopher T CheckJames P Stambuli
Feb 5, 2011·Journal of the American Chemical Society·Alexandre LumbrosoBernhard Breit
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Nov 13, 2014·Journal of the American Chemical Society·Ba L TranJohn F Hartwig
Jun 12, 2019·Journal of the American Chemical Society·Jonathan N JaworskiShannon S Stahl

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