Synthesis of 1,1'-Diarylethanes and Related Systems by Displacement of Trichloroacetimidates with Trimethylaluminum

The Journal of Organic Chemistry
Nivedita S Mahajani, John D Chisholm

Abstract

Benzylic trichloroacetimidates are readily displaced by trimethylaluminum under Lewis acid promoted conditions to provide the corresponding methyl substitution product. This method is a convenient way to access 1,1'-diarylethanes and related systems, which play a significant role in medicinal chemistry, with a number of systems owing their biological activity to this functionality. Most benzylic substrates undergo ready displacement, with electron deficient systems being the exception. The use of an enantiopure imidate showed significant racemization, implicating the formation of a cationic intermediate.

References

Apr 18, 1995·Carbohydrate Research·J S Andrews, B M Pinto
Dec 4, 2003·Bioorganic & Medicinal Chemistry Letters·F P BymasterD T Wong
Oct 9, 2007·Bioorganic & Medicinal Chemistry Letters·Hirotaka Tanaka, Yuji Shishido
Aug 12, 2009·Journal of Medicinal Chemistry·Wilna J MoreeGraham Beaton
Oct 12, 2010·Chemistry, an Asian Journal·Hidetoshi TokuyamaTohru Fukuyama
Dec 16, 2010·Journal of the American Chemical Society·Buck L H TaylorElizabeth R Jarvo
Jan 27, 2011·Chemistry : a European Journal·Pau Ruiz-SanchisMercedes Álvarez
Aug 2, 2011·The Journal of Organic Chemistry·Ravindra T DereRichard R Schmidt
Nov 19, 2011·The Journal of Organic Chemistry·Evangelina RepettoOscar Varela
Mar 8, 2012·The Journal of Organic Chemistry·Joshua A HartselPaul R Carlier
Apr 13, 2012·The Journal of Organic Chemistry·Yuta SuzukiMasakatsu Shibasaki
Aug 21, 2013·Journal of the American Chemical Society·Tetsuya IdeguchiToshiaki Sunazuka
May 27, 2014·The Journal of Organic Chemistry·Masami KuriyamaOsamu Onomura
Aug 8, 2014·Chemical Communications : Chem Comm·Yan-Yan SunYao Fu
Oct 14, 2014·Journal of the American Chemical Society·Emily J TollefsonElizabeth R Jarvo
Dec 9, 2014·Journal of the American Chemical Society·Zhaobin WangJianwei Sun
Jan 9, 2015·The Journal of Organic Chemistry·Daniel R WallachJohn D Chisholm
Jul 7, 2015·Chemistry : a European Journal·Takeshi YamadaToshiaki Sunazuka
Jul 22, 2015·Accounts of Chemical Research·Emily J TollefsonElizabeth R Jarvo
Sep 30, 2015·Angewandte Chemie·Indranil ChatterjeeMartin Oestreich
Dec 23, 2015·Organic & Biomolecular Chemistry·Kyle T HowardJohn D Chisholm
Aug 4, 2016·The Journal of Organic Chemistry·Daniel R Wallach, John D Chisholm
Oct 7, 2016·Chemical Communications : Chem Comm·Soumitra AgastiDebabrata Maiti
Jan 24, 2017·Journal of the American Chemical Society·Yu-Xin LuanMengchun Ye
Mar 23, 2017·The Journal of Organic Chemistry·Arijit A AdhikariJohn D Chisholm
Jun 1, 2017·Journal of the American Chemical Society·Wen ZhangGuosheng Liu
Jul 25, 2017·Journal of the American Chemical Society·Joseph DerosaKeary M Engle
Aug 5, 2017·Chemical Communications : Chem Comm·Masahito MuraiKazuhiko Takai

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Citations

Nov 14, 2019·Organic & Biomolecular Chemistry·Rima ThakurAmit Kumar
May 24, 2019·The Journal of Organic Chemistry·Nivedita S MahajaniJohn D Chisholm

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