Palladium-catalyzed conjugate allylation reactions of alpha,beta-unsaturated N-acylpyrroles.
Conjugate allylation reactions of alpha,beta-unsaturated N-acylpyrroles using allylboronic ester are catalyzed by a palladium complex that is ligated by a bidentate N-heterocyclic carbene. A variety of functional groups are tolerated, and substrates functionalized with electron-withdrawing groups react to afford the highest yields of products. Regioselectivity for 1,4-allylation over 1,2-allylation is demonstrated, and mechanistic experiments are consistent with formation of nucleophilic allylpalladium intermediates.
Shaghafi
Michael B
MB
Natural Sciences I 4114, Department of Chemistry, University of California, Irvine, California 92697, USA.
Kohn
Benjamin L
BL
Jarvo
Elizabeth R
ER
D000215:Acylation; D000498:Allyl Compounds / Q000737:chemistry*; D002384:Catalysis; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry*; D011758:Pyrroles / Q000737:chemistry*
D000498:Allyl Compounds; D011758:Pyrroles; D010165:Palladium