Nickel-catalyzed, carbonyl-ene-type reactions: selective for alpha olefins and more efficient with electron-rich aldehydes.

Journal of the American Chemical Society
Chun-Yu HoTimothy F Jamison

Abstract

Described are several classes of unusual or unprecedented carbonyl-ene-type reactions, including those between alpha olefins and aromatic aldehydes. Catalyzed by nickel, these processes complement existing Lewis acid-catalyzed methods in several respects. Not only are monosubstituted alkenes, aromatic aldehydes, and tert-alkyl aldehydes effective substrates, but monosubstituted olefins also react faster than those that are more substituted, and large or electron-rich aldehydes are more effective than small or electron-poor ones. Conceptually, in the presence of a nickel-phosphine catalyst, the combination of off-the-shelf alkenes, silyl triflates, and triethylamine functions as a replacement for an allylmetal reagent.

References

May 10, 2002·Organic Letters·Yike NiJohn Montgomery

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Citations

Aug 31, 2006·Journal of the American Chemical Society·Sze-Sze NgTimothy F Jamison
Nov 1, 2007·Chemical Communications : Chem Comm·Ryan M MoslinTimothy F Jamison
May 4, 2010·Journal of the American Chemical Society·Ryosuke Matsubara, Timothy F Jamison
Nov 10, 2011·Journal of the American Chemical Society·Ryosuke MatsubaraTimothy F Jamison
Nov 4, 2006·Chemical Communications : Chem Comm·Masahiro Murakami, Shinji Ashida
Feb 1, 2008·Angewandte Chemie·Chun-Yu HoTimothy F Jamison
Mar 10, 2011·Chemistry, an Asian Journal·Ryosuke Matsubara, Timothy F Jamison
Mar 26, 2011·Chemical Science·Holly A Reichard, Glenn C Micalizio
Aug 7, 2012·Chemistry : a European Journal·Subramaniyan Mannathan, Chien-Hong Cheng
Jun 5, 2013·Chemistry : a European Journal·Lingyun CuiJin-Pei Cheng
Apr 24, 2015·Accounts of Chemical Research·Eric A StandleyTimothy F Jamison
Sep 4, 2018·Organometallics·Jessica M WeberTimothy F Jamison

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