Premium
Palladium(II) Acetate Catalyzed Reductive Heck Reaction of Enones; A Practical Approach
Author(s) -
Mannathan Subramaniyan,
Raoufmoghaddam Saeed,
Reek Joost N. H.,
de Vries Johannes G.,
Minnaard Adriaan J.
Publication year - 2015
Publication title -
chemcatchem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.497
H-Index - 106
eISSN - 1867-3899
pISSN - 1867-3880
DOI - 10.1002/cctc.201500760
Subject(s) - heck reaction , chemistry , aryl , reductive elimination , palladium , catalysis , medicinal chemistry , organic chemistry , alkyl
A surprisingly practical Pd(OAc) 2 or Pd(TFA) 2 ‐catalyzed reductive Heck reaction between aryl iodides and α,β‐unsaturated ketones is described using N,N ‐diisopropylethylamine (DIPEA, Hünigs base) as the reductant. In general, 1 mol % of Pd(OAc) 2 is sufficient to afford good yields using electron‐rich or halogen‐substituted aryl iodides. Electron‐deficient aryl iodides preferentially give homocoupling. Enones containing aryl or bulky substituents on the β‐carbon react smoothly, producing mainly reductive Heck product, whereas enones with alkyl substituents on the β‐carbon afford a mixture of reductive Heck and Heck product. Deuterium labeling experiments show that the reaction is a bona fide reductive Heck reaction and exclude a Heck reaction‐conjugate reduction cascade.