Regioselective control by a catalyst switch in palladium-catalyzed benzylallylation of arylethylidene malononitriles
Release Time:2019-03-09 Hits:
Indexed by: Journal Article
Date of Publication: 2013-11-15
Journal: JOURNAL OF ORGANOMETALLIC CHEMISTRY
Included Journals: Scopus、EI、SCIE
Volume: 745
Page Number: 177-185
ISSN: 0022-328X
Key Words: Regioselective control; Catalyst switch; 2-(Bromomethylnaphthalene; Arylethylidene malononitrile; Allyltributylstannane
Abstract: Regioselective control by a catalyst switch in palladium-catalyzed benzylallylation of arylethylidene malononitriles (alpha-benzyl-beta-allylation versus alpha-allyl-beta-benzylation) is described. The three-component reaction of 2-(bromomethyl)naphthalenes, arylethylidene malononitriles, and allyltributylstannane proceeds smoothly with palladium nanoparticles as a catalyst to provide a-benzyl-b-allylation products in good yields. The regioselectivity of the benzylallylation reaction is completely overturned with Pd(PPh3)(4) as the catalyst instead of palladium nanoparticles to obtain alpha-allyl-beta-benzylation products in moderate to good yields. (C) 2013 Elsevier B.V. All rights reserved.
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