Synthesis of Borylcyclopropanes by Chromium-Promoted Cyclopropanation of Unactivated Alkenes

Organic Letters
Masahito MuraiKazuhiko Takai

Abstract

The combination of diiodomethylboronate ester, CrCl2 with TMEDA promoted borylcyclopropanation of unactivated alkenes under mild conditions. Compared with the typical Simmons-Smith cyclopropanation, the current protocol offers the following advantages: (1) the reaction proceeds stereoselectively with disubstituted alkenes even without hydroxy or alkoxy groups; (2) both electron-rich and electron-deficient alkenes can be applicable; and (3) the reaction does not require potentially flammable alkylzinc. These unique reactivity features result from the steric and electronic nature of the gem-dichromiomethane intermediates.

References

Jul 4, 2001·Angewandte Chemie·Rüdiger Faust
Dec 26, 2001·Chemical Reviews·A de Meijere, S I Kozhushkov
Dec 19, 1996·Chemical Reviews·Ilane Marek, Jean-F. Normant
Apr 10, 2003·Chemical Reviews·Hélène LebelAndré B Charette
Apr 10, 2003·Chemical Reviews·Frieder Gnad, Oliver Reiser
Apr 10, 2003·Chemical Reviews·Ludger A WessjohannThies Thiemann
Jun 12, 2003·Journal of the American Chemical Society·Marina RubinaVladimir Gevorgyan
Jul 12, 2007·Chemical Reviews·Michael RubinVladimir Gevorgyan
Jul 25, 2007·Angewandte Chemie·Takuya KurahashiArmin de Meijere
Jan 30, 2008·Organic Letters·Yasutaka Fujioka, Hideki Amii
Dec 24, 2009·Chemical Reviews·Ibraheem A I MkhalidJohn F Hartwig
May 18, 2012·Chemical Society Reviews·David Y-K ChenJean-Alexandre Richard
Feb 21, 2013·Journal of the American Chemical Society·Carl W Liskey, John F Hartwig
Sep 24, 2013·Journal of the American Chemical Society·Andreas K SteibPaul Knochel
Apr 29, 2014·Angewandte Chemie·Tobias F SchneiderDaniel B Werz
Oct 24, 2014·Journal of the American Chemical Society·Alejandro ParraMariola Tortosa
Jan 19, 2017·Journal of the American Chemical Society·Guillaume Benoit, André B Charette
May 4, 2017·Chemical Reviews·Christian Ebner, Erick M Carreira
Nov 2, 1998·Angewandte Chemie·Shao-Man ZhouMing-Hua Tang

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Citations

Oct 3, 2018·Angewandte Chemie·Morgane SayesAndré B Charette
Jan 3, 2019·Angewandte Chemie·Laura AmenósMariola Tortosa
Feb 16, 2019·Chemical Communications : Chem Comm·Masahito MuraiKazuhiko Takai
Dec 4, 2019·Organic & Biomolecular Chemistry·Qiang LiuXiaoxia Wang

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