Synthesis of difluoromethyl and deuterium-labeled difluoromethyl thioethers from aliphatic electrophiles

Chemical Communications : Chem Comm
Tianqi DingWenbin Yi

Abstract

A one-pot difluoromethylthiolation of alkyl electrophiles with thiourea and diethyl bromodifluoromethylphosphonate is described. The transition-metal-free approach, readily available reagents, and mild conditions provide a practical way for the synthesis of difluoromethyl thioethers. By changing the "H" source to the most commonly used "D" sources CD3OD and D2O, this strategy enables efficient synthesis of SCF2D-substituted molecules in good yields with high levels of D incorporation.

References

Dec 13, 2002·Journal of Medicinal Chemistry·J HelfenbeinJ C Madelmont
Jun 19, 2004·Science·Masaaki MiyashitaKeiji Tanino
Mar 10, 2005·Chemical Reviews·Frédéric LerouxManfred Schlosser
Sep 29, 2007·Science·Klaus MüllerFrançois Diederich
Jan 17, 2008·Chemical Society Reviews·Sophie PurserVéronique Gouverneur
Jun 24, 2008·Journal of Medicinal Chemistry·William K Hagmann
Mar 19, 2011·Journal of Medicinal Chemistry·Nicholas A Meanwell
Jan 13, 2012·Journal of the American Chemical Society·Kyle W QuasdorfNeil K Garg
Jan 12, 2013·Angewandte Chemie·Patrick S Fier, John F Hartwig
Jun 8, 2013·Nature Medicine·Alla Katsnelson
Jul 13, 2013·Chemistry, an Asian Journal·Hui Liu, Xuefeng Jiang
Sep 26, 2013·Organic Letters·Vaibhav P Mehta, Michael F Greaney
Mar 14, 2013·ACS Medicinal Chemistry Letters·Yaoqiu ZhuBo Jiao
Jul 30, 2014·Expert Opinion on Therapeutic Patents·Graham S Timmins
Dec 17, 2014·Bioorganic & Medicinal Chemistry Letters·Charles S Elmore, Ryan A Bragg
Apr 29, 2015·Chemical Communications : Chem Comm·Xiao-Yun DengJi-Chang Xiao
Jul 17, 2015·Journal of the American Chemical Society·Dianhu ZhuQilong Shen
Sep 4, 2015·Chemistry : a European Journal·Kévin JouvinLukas J Goossen
Sep 16, 2015·Current Topics in Medicinal Chemistry·Minghao FengXuefeng Jiang
Jan 13, 2016·Organic Letters·Ya-Mei LinGuo-Ping Lu
Jan 15, 2016·Nature·Renyuan Pony YuPaul J Chirik
Apr 2, 2016·Nature Reviews. Drug Discovery·Asher Mullard
Apr 3, 2016·Angewandte Chemie·Ermal IsmalajThierry Billard
Jun 17, 2016·Chemical Communications : Chem Comm·Joseph L HowardDuncan L Browne
Oct 7, 2016·Journal of the American Chemical Society·Lillian V A Hale, Nathaniel K Szymczak
Jun 8, 2017·Nature Biotechnology·Charles Schmidt
Aug 18, 2017·Angewandte Chemie·Jens AtzrodtMarc Reid
Nov 17, 2017·Angewandte Chemie·Jiao YuJi-Chang Xiao
Jan 30, 2018·Journal of the American Chemical Society·J Luke KoniarczykAndrew McNally
Apr 11, 2018·Topics in Current Chemistry·Ming Wang, Xuefeng Jiang
Aug 5, 2018·Journal of the American Chemical Society·Xin WangWen-Bo Liu
Oct 24, 2018·Angewandte Chemie·Muliang ZhangJin Xie
Nov 21, 2018·Angewandte Chemie·Jan SklyarukMagnus Rueping
Jan 10, 2019·Journal of the American Chemical Society·Thomas R PuleoJeffrey S Bandar

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Citations

Sep 4, 2021·The Journal of Organic Chemistry·Min ZhangJi-Chang Xiao

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