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Highly Efficient Palladium‐Catalyzed Allylic Alkylation of Cyanoacetamides with Controllable and Chemoselective Mono‐ and Double Substitutions
Author(s) -
Gao PeiSen,
Li Ning,
Zhang JinLei,
Zhu ZhuangLi,
Gao ZiWei,
Sun HuaMing,
Zhang WeiQiang,
Xu LiWen
Publication year - 2016
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.201601021
Subject(s) - regioselectivity , chemistry , ligand (biochemistry) , catalysis , palladium , ethylene glycol , triazine , combinatorial chemistry , peg ratio , phosphine , yield (engineering) , alkylation , organic chemistry , polymer chemistry , materials science , biochemistry , receptor , finance , economics , metallurgy
It was found that catalytic allylation of various cyanoacetamides proceeded smoothly and efficiently in environmentally benign PEG‐400 (PEG=poly(ethylene glycol)) in the presence of Pd(OAc) 2 and novel triazine‐derived multifunctional ligand L1 , with which this reaction could afford the structurally diverse mono‐ and double allylated adducts in good to excellent yields as well as good chemo‐ and regioselectivity. In addition, this Pd/ L1 /PEG‐400 catalyst system could be recycled for five runs with good yield and high efficiency, which supported the notion that the triazine‐containing Schiff base based phosphine ligand could be a multifunctional and reusable ligand encapsulated in PEG‐400.