Iridium-catalyzed alpha-alkylation of acetates with primary alcohols and diols

Journal of the American Chemical Society
Yosuke IuchiYasutaka Ishii

Abstract

Acetates were successfully alkylated with primary alcohols and alpha,omega-diols in the presence of tert-BuOK under the influence of [IrCl(cod)](2). For instance, the reaction of tert-butyl acetate with n-butanol in the presence of tert-BuOK as a base and [IrCl(cod)](2) as a catalyst in tert-BuOH at 100 degrees C produced tert-butyl hexanoate in good yield. When the alpha,omega-diol 1,9-nonanediol was employed, di-tert-butyl tridecanoate was obtained. These reactions are the first report of the alkylation of acetates using alcohols as alkylating agents. This method provides a very convenient direct route to carboxylates, which are very important raw materials in organic and industrial chemistry.

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Citations

Sep 28, 2012·The Journal of Organic Chemistry·Yasushi OboraNobuyuki Yamamoto
Jul 8, 2011·Organic Letters·Bruno AnxionnatJanine Cossy
Aug 31, 2012·Organic Letters·Takashi KuwaharaIlhyong Ryu
Dec 4, 2013·Organic Letters·Yang LiJianliang Xiao
Aug 31, 2016·Topics in Current Chemistry·Yasushi Obora
Aug 5, 2016·Journal of the American Chemical Society·Nicklas Deibl, Rhett Kempe
Mar 4, 2017·The Journal of Organic Chemistry·Tong-Yu FengJian-Ping Lang
Oct 11, 2016·Organic & Biomolecular Chemistry·Moreshwar Bhagwan ChaudhariBoopathy Gnanaprakasam
Mar 23, 2019·Organic & Biomolecular Chemistry·Meng-Juan ZhangJian-Ping Lang
Jun 27, 2019·ChemSusChem·Priyanka ChakrabortyBasker Sundararaju
Aug 4, 2011·Angewandte Chemie·Yasushi OboraYasutaka Ishii
Jan 25, 2014·Chemical Communications : Chem Comm·Shinji Ogawa, Yasushi Obora
Jan 16, 2015·Chemistry : a European Journal·Xu QuanPher G Andersson
May 30, 2012·Chemical Communications : Chem Comm·Yasushi OboraShintaro Hatanaka
Feb 18, 2021·Organic & Biomolecular Chemistry·Masaki KobayashiYasushi Obora
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Aug 14, 2020·The Journal of Organic Chemistry·Masaki KobayashiYasushi Obora
Apr 23, 2019·ACS Catalysis·Subrata ChakrabortyDavid Milstein

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