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Chugaev‐type bis(acyclic diaminocarbenes) as a new ligand class for the palladium‐catalyzed Mizoroki–Heck reaction
Author(s) -
Owusu Millicent O.,
Handa Sachin,
Slaughter LeGrande M.
Publication year - 2012
Publication title -
applied organometallic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.53
H-Index - 71
eISSN - 1099-0739
pISSN - 0268-2605
DOI - 10.1002/aoc.2915
Subject(s) - chemistry , aryl , catalysis , heck reaction , palladium , ligand (biochemistry) , carbene , combinatorial chemistry , organic chemistry , styrene , coupling reaction , polymer chemistry , copolymer , alkyl , biochemistry , receptor , polymer
A series of differently substituted Chugaev‐type palladium bis(acyclic diaminocarbene) complexes was screened to identify the most active catalyst for Mizoroki–Heck coupling reactions of aryl bromides with styrene. The best catalyst, which contains three methyl groups on the bis(carbene) ligand, gives excellent coupling yields at 120 °C for both activated and deactivated aryl bromides. However, activity with aryl chlorides is limited to electron‐deficient examples. The optimized catalyst demonstrates limited air and moisture stability, giving reduced yields in couplings of activated aryl bromides in open‐flask conditions. The modular synthesis of this class of catalysts should allow further fine‐tuning of activity in Mizoroki–Heck and related coupling reactions . Copyright © 2012 John Wiley & Sons, Ltd.