Crystalline Radicals Derived from Classical N-Heterocyclic Carbenes

Angewandte Chemie
Dennis RottschäferRajendra S Ghadwal

Abstract

One-electron reduction of C2-arylated 1,3-imidazoli(ni)um salts (IPrAr )Br (Ar=Ph, 3 a; 4-DMP, 3 b; 4-DMP=4-Me2 NC6 H4 ) and (SIPrAr )I (Ar=Ph, 4 a; 4-Tol, 4 b) derived from classical NHCs (IPr=:C{N(2,6-iPr2 C6 H3 )}2 CHCH, 1; SIPr=:C{N(2,6-iPr2 C6 H3 )}2 CH2 CH2 , 2) gave radicals [(IPrAr )]. (Ar=Ph, 5 a; 4-DMP, 5 b) and [(SIPrAr )]. (Ar=Ph, 6 a; 4-Tol, 6 b). Each of 5 a,b and 6 a,b exhibited a doublet EPR signal, a characteristic of monoradical species. The first solid-state characterization of NHC-derived carbon-centered radicals 6 a,b by single-crystal X-ray diffraction is reported. DFT calculations indicate that the unpaired electron is mainly located at the original carbene carbon atom and stabilized by partial delocalization over the adjacent aryl group.

References

Nov 2, 2002·Angewandte Chemie·Hansjörg Grützmacher, Frank Breher
Sep 18, 2003·Journal of the American Chemical Society·Iain McKenzieJason A C Clyburne
Jul 18, 2009·Journal of the American Chemical Society·Shau-Hua UengDennis P Curran
Jan 1, 2010·Acta Crystallographica. Section E, Structure Reports Online·Nick A GiffinJason D Masuda
Sep 10, 2011·Dalton Transactions : an International Journal of Inorganic Chemistry·Yuzhong Wang, Gregory H Robinson
Nov 28, 2012·Accounts of Chemical Research·Rajendra S GhadwalHerbert W Roesky
Jul 24, 2013·Chemical Science·Caleb D MartinGuy Bertrand
Jul 26, 2013·Chemical Reviews·Manabu Abe
Dec 7, 2013·Journal of the American Chemical Society·Janell K MahoneyGuy Bertrand
Jun 27, 2014·Nature·Matthew N HopkinsonFrank Glorius
Oct 25, 2014·Inorganic Chemistry·Yuzhong Wang, Gregory H Robinson
Dec 18, 2014·Accounts of Chemical Research·Michèle Soleilhavoup, Guy Bertrand
Feb 3, 2015·Chemistry : a European Journal·Rajendra S GhadwalRegine Herbst-Irmer
May 1, 2015·Chemistry : a European Journal·Steffen StyraGuy Bertrand
May 27, 2015·Journal of the American Chemical Society·Janell K MahoneyGuy Bertrand
Nov 21, 2015·Chemical Society Reviews·Kartik Chandra MondalHerbert W Roesky
Dec 18, 2015·Inorganic Chemistry·Kartik Chandra MondalHerbert W Roesky
Oct 19, 2016·Dalton Transactions : an International Journal of Inorganic Chemistry·Rajendra S Ghadwal
Dec 10, 2016·Journal of the American Chemical Society·Léonard Y M EymannKay Severin
Jan 20, 2017·Journal of the American Chemical Society·Holger BraunschweigQing Ye
Apr 5, 2017·Angewandte Chemie·Mohand MelaimiGuy Bertrand
May 10, 2017·Journal of the American Chemical Society·Yuzhong WangGregory H Robinson
May 26, 2017·Angewandte Chemie·Lianghu GuManuel Alcarazo
Jun 3, 2017·Dalton Transactions : an International Journal of Inorganic Chemistry·Rajendra S GhadwalSerhiy Demeshko
Jul 21, 2017·Accounts of Chemical Research·Shenglai YaoMatthias Driess
Jul 27, 2017·Journal of the American Chemical Society·Subrata KunduHerbert W Roesky
Aug 24, 2017·Chemistry : a European Journal·Dennis RottschäferRajendra S Ghadwal
Aug 31, 2017·Dalton Transactions : an International Journal of Inorganic Chemistry·Nga Kim T HoRajendra S Ghadwal
Oct 19, 2017·Journal of the American Chemical Society·Jisu BackEunsung Lee
Oct 20, 2017·Journal of the American Chemical Society·Max M HansmannGuy Bertrand
Nov 4, 2017·Journal of the American Chemical Society·John C WaltonDennis P Curran
Dec 22, 2017·Journal of the American Chemical Society·Subrata KunduHerbert W Roesky
Jan 18, 2018·Journal of the American Chemical Society·Max M HansmannGuy Bertrand
Feb 1, 2018·Journal of the American Chemical Society·Max M HansmannGuy Bertrand

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Citations

Apr 19, 2018·Angewandte Chemie·Dennis RottschäferRajendra S Ghadwal
Jun 23, 2018·Chemical Communications : Chem Comm·Mirko RuampsVincent César
Jul 6, 2018·Angewandte Chemie·Mujahuddin M SiddiquiHerbert W Roesky
Oct 5, 2018·Journal of Computational Chemistry·Evgeniy G Gordeev, Valentine P Ananikov
Sep 7, 2018·Chemistry : a European Journal·Dennis RottschäferRajendra S Ghadwal
Jul 31, 2018·Chemistry : a European Journal·Youngsuk Kim, Eunsung Lee
Dec 19, 2018·Angewandte Chemie·F Mark ChadwickKay Severin
Feb 13, 2019·Angewandte Chemie·Kenichi Kato, Atsuhiro Osuka
Jul 16, 2019·Chemistry : a European Journal·Marco WerrHans-Jörg Himmel
Oct 15, 2019·Chemistry : a European Journal·Gargi KunduSakya S Sen
Jan 23, 2020·Chemical Communications : Chem Comm·Dennis RottschäferRajendra S Ghadwal
Feb 28, 2020·Chemical Communications : Chem Comm·Mahendra K SharmaRajendra S Ghadwal
Apr 12, 2020·Angewandte Chemie·Eder Tomás-MendivilDavid Martin
Jun 26, 2018·Chemical Science·Dennis RottschäferRajendra S Ghadwal
Aug 14, 2019·Chemical Communications : Chem Comm·Mahendra K SharmaRajendra S Ghadwal
Jun 5, 2019·Chemical Science·Subrata KunduHerbert W Roesky
May 31, 2019·Chemical Communications : Chem Comm·Youngsuk KimEunsung Lee
Nov 7, 2020·Angewandte Chemie·Arne MerschelRajendra S Ghadwal
Nov 3, 2020·Chemistry : a European Journal·Diya ZhuDouglas W Stephan
May 12, 2021·Journal of the American Chemical Society·Youngsuk KimEunsung Lee
Jul 4, 2018·Chemical Reviews·Vitaly NesterovShigeyoshi Inoue
Dec 8, 2020·The Journal of Organic Chemistry·Arpan DasSwadhin K Mandal
May 28, 2019·Journal of the American Chemical Society·Patrick W AntoniMax M Hansmann
Oct 24, 2018·Journal of the American Chemical Society·Patrick W Antoni, Max M Hansmann
Sep 2, 2021·Journal of the American Chemical Society·Jing ZhaoYing-Feng Han

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