Regiospecific decarboxylative allylation of nitriles.

Organic Letters
Antonio Recio, Jon A Tunge

Abstract

Palladium-catalyzed decarboxylative alpha-allylation of nitriles readily occurs with use of Pd(2)(dba)(3) and rac-BINAP. This catalyst mixture also allows the highly regiospecific alpha-allylation of nitriles in the presence of much more acidic alpha-protons. Thus, the reported method provides access to compounds that are not readily available via base-mediated allylation chemistries. Lastly, mechanistic investigations indicate that there is a competition between C- and N-allylation of an intermediate nitrile-stabilized anion and that N-allylation is followed by a rapid [3,3]-sigmatropic rearrangement.

References

Mar 12, 2005·The Journal of Organic Chemistry·Fraser F FlemingPaul Knochel
Sep 30, 2005·Journal of the American Chemical Society·Dinesh Kumar Rayabarapu, Jon A Tunge
Aug 3, 2006·Journal of the American Chemical Society·Erin C Burger, Jon A Tunge
Aug 31, 2006·Journal of the American Chemical Society·Justin T MohrBrian M Stoltz
Mar 21, 2007·Journal of the American Chemical Society·Shelli R Waetzig, Jon A Tunge
Jun 22, 2007·Organic Letters·Andrew A Yeagley, Jason J Chruma
Aug 11, 2007·Angewandte Chemie·Fraser F FlemingOmar W Steward
Sep 11, 2007·Journal of the American Chemical Society·John A KeithWilliam A Goddard
Jan 23, 2008·Chemical Communications : Chem Comm·Jean-Marc Gaudin, Pascal Millet
Mar 14, 2008·The Journal of Organic Chemistry·Fraser F FlemingOmar W Steward
Jun 7, 2008·Journal of the American Chemical Society·Chao Wang, Jon A Tunge
Sep 13, 2008·Organic Letters·Jimmie D Weaver, Jon A Tunge

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Citations

Jan 18, 2011·Chemical Reviews·Jimmie D WeaverJon A Tunge
Aug 19, 2010·Journal of the American Chemical Society·Jimmie D WeaverJon A Tunge
Aug 13, 2011·Journal of the American Chemical Society·Alexander J Grenning, Jon A Tunge
Jul 26, 2014·Journal of the American Chemical Society·Alexander J GrenningJohn A Porco
Jan 16, 2015·Organic Letters·Peter J Lindsay-ScottJeffery Richardson
Sep 23, 2014·Organic Letters·Tapan Maji, Jon A Tunge
Nov 8, 2011·Angewandte Chemie·Dinesh Nath, Fraser F Fleming
Sep 24, 2014·Organic & Biomolecular Chemistry·Yamuna Ariyarathna, Jon A Tunge
Nov 8, 2011·Chemical Communications : Chem Comm·Antonio RecioJon A Tunge
Nov 1, 2016·Chemistry : a European Journal·Theresa M Locascio, Jon A Tunge
Nov 20, 2016·Angewandte Chemie·Ouidad LahtiguiAlexander J Grenning
Nov 18, 2016·Organic & Biomolecular Chemistry·Primali V Navaratne, Alexander J Grenning
Oct 2, 2014·Chemical Communications : Chem Comm·Yamuna Ariyarathna, Jon A Tunge
May 21, 2010·Organic Letters·Bhaskar Reddy Pitta, Fraser F Fleming

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