Generation of bis-acyl ketals from esters and benzyl amines under oxidative conditions

The Journal of Organic Chemistry
Ganesh MajjiBhisma K Patel

Abstract

Treatment of benzylamines with esters at an elevated temperature are expected to give amides. However, in the presence of TBAI/TBHP, esters possessing a methylene carbon α-to oxygen with benzylamines provide bis-esters rather than the expected amides. Benzylamines under oxidative conditions generate less nucleophilic carboxylates, which couples at the sp(3) C-H bonds of esters and cyclic ethers to give bis-acyl ketals and α-acyloxy ethers, respectively.

References

May 18, 2000·The Journal of Organic Chemistry·D J Kopecky, S D Rychnovsky
Feb 1, 1996·Chemical Reviews·Paul A. Wender
May 21, 2004·Organic Letters·Yongda Zhang, Tomislav Rovis
May 21, 2005·The Journal of Organic Chemistry·Mark A HuffmanJames M McNamara
Jun 7, 2006·Proceedings of the National Academy of Sciences of the United States of America·Zhiping LiChao-Jun Li
Mar 19, 2009·Angewandte Chemie·Noah Z BurnsReinhard W Hoffmann
Jun 15, 2010·The Journal of Organic Chemistry·Tanja Gaich, Phil S Baran
Mar 10, 2011·Chemistry : a European Journal·Long ChenXiaobing Wan
Jan 1, 2010·Topics in Current Chemistry·Woo-Jin Yoo, Chao-Jun Li
Jun 15, 2011·Chemical Society Reviews·Joanna Wencel-DelordFrank Glorius
Oct 25, 2011·Accounts of Chemical Research·Tobias BrücklPhil S Baran
May 5, 2012·Accounts of Chemical Research·Sharon R Neufeldt, Melanie S Sanford
Mar 7, 2013·Chemical Communications : Chem Comm·Ganesh MajjiBhisma K Patel
Aug 31, 2013·Organic Letters·Sheng-rong GuoJian-nan Xiang
Mar 13, 2014·Chemical Communications : Chem Comm·Lingfeng GaoZhiyong Wang
Jul 18, 2014·Organic & Biomolecular Chemistry·Quan WangRongxin Yuan

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Citations

Aug 5, 2016·Organic & Biomolecular Chemistry·Ganesh MajjiBhisma K Patel
Mar 8, 2018·Chemical Record : an Official Publication of the Chemical Society of Japan ... [et Al.]·Rongxiang ChenXiaobing Wan
Jun 3, 2015·The Journal of Organic Chemistry·Ana Leticia García-CabezaFrancisco M Guerra

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