Isolable Anionic, Neutral and Cationic Radicals from Reactions of  N,N'-dimesityldiamidocarbene and Lewis Acids

Chemistry : a European Journal
Ryan Andrews, Douglas Wade Stephan

Abstract

B(C 6 F 5 ) 3 undergoes nucleophilic attack by N,N'-dimesityldiamidocarbene (DAC) with fluoride transfer to the boron center, resulting in a zwitterion (1). This B-F can be replaced or abstracted to give the corresponding hydride (2) or triflate (3) derivatives or the corresponding cation (4).  These species are reduced with KC 8 or Cp 2 Co to give isolable anionic and neutral radicals (5-8). Similarly, the [Ph 3 C] cation undergoes nucleophilic attack by DAC resulting in the spontaneous formation of the radical cation (9).

References

Nov 18, 2006·Science·Gregory C WelchDouglas W Stephan
Apr 3, 2007·Angewandte Chemie·Ching-Wen Chiu, François P Gabbaï
Aug 1, 2007·Dalton Transactions : an International Journal of Inorganic Chemistry·Gregory C WelchDouglas W Stephan
Aug 19, 2007·Angewandte Chemie·Preston A ChaseDouglas W Stephan
Feb 21, 2008·Inorganic Chemistry·Gregory C WelchDouglas W Stephan
Jul 18, 2009·Journal of the American Chemical Society·Shau-Hua UengDennis P Curran
Jan 22, 2010·Angewandte Chemie·Stefan GrimmeGerhard Erker
Jan 29, 2010·Journal of the American Chemical Society·John C WaltonDennis P Curran
May 19, 2010·Chemical Communications : Chem Comm·Todd W HudnallChristopher W Bielawski
Jul 5, 2011·Angewandte Chemie·Allan Jay P CardenasGerhard Erker
Feb 16, 2012·Angewandte Chemie·Holger BraunschweigJohannes Wahler
May 3, 2012·Journal of the American Chemical Society·Muhammad SajidGerhard Erker
Dec 4, 2012·Dalton Transactions : an International Journal of Inorganic Chemistry·Elliot J LawrenceAndrew E Ashley
Dec 5, 2012·Journal of the American Chemical Society·Yoshitaka AramakiKyoko Nozaki
Apr 19, 2013·Journal of the American Chemical Society·Gabriel MénardDouglas W Stephan
Nov 13, 2013·Dalton Transactions : an International Journal of Inorganic Chemistry·Eileen TheuergartenMatthias Tamm
Jun 12, 2014·Angewandte Chemie·Philipp BissingerShun Sugawara
May 15, 2015·Angewandte Chemie·Douglas W Stephan, Gerhard Erker
Jul 28, 2015·Journal of the American Chemical Society·Douglas W Stephan
Feb 5, 2016·Dalton Transactions : an International Journal of Inorganic Chemistry·Anthony D Ledet, Todd W Hudnall
Dec 13, 2016·Science·Douglas W Stephan
Dec 21, 2016·Angewandte Chemie·Miguel F Silva ValverdeMatthias Tamm
Jun 28, 2017·Journal of the American Chemical Society·Liu Leo LiuDouglas W Stephan
Oct 28, 2017·The Journal of Physical Chemistry. a·Adrian Y Houghton, Tom Autrey
Feb 8, 2018·Chemistry : a European Journal·Levy L CaoDouglas W Stephan
May 22, 2018·Chemical Communications : Chem Comm·Liu Leo LiuDouglas W Stephan
Jul 27, 2018·Chemical Communications : Chem Comm·Dipak Kumar RoyHolger Braunschweig
Oct 24, 2018·Chemical Reviews·Miao HongEugene Y-X Chen
Oct 26, 2018·Journal of the American Chemical Society·Zhaowen DongThomas Müller
Feb 7, 2019·Chemical Society Reviews·Liu Leo Liu, Douglas W Stephan
Apr 11, 2019·Angewandte Chemie·Elliot L BennettJ Chris Slootweg

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Citations

Sep 16, 2020·Angewandte Chemie·Ayan DasguptaRebecca L Melen
Mar 3, 2021·Journal of the American Chemical Society·Avijit MaitiAnukul Jana

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