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Direct Synthesis of Protected Arylacetaldehydes by Tetrakis(phosphane)palladium‐Catalyzed Arylation of Ethyleneglycol Vinyl Ether
Author(s) -
Kondolff Isabelle,
Doucet Henri,
Santelli Maurice
Publication year - 2006
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200500540
Subject(s) - chemistry , aryl , vinyl ether , catalysis , cyclopentane , palladium , ether , ethylene glycol , steric effects , medicinal chemistry , organic chemistry , polymer chemistry , alkyl , copolymer , polymer
Abstract A range of aryl bromides undergo Heck reaction with ethylene glycol vinyl ether, in the presence of [PdCl(C 3 H 5 )] 2 / cis , cis , cis ‐1,2,3,4‐tetrakis[(diphenylphosphanyl)methyl]cyclopentane as catalyst, to give regioselectively protected arylacetaldehydes in good yields. The β‐arylation products were obtained in with 93–100 % selectivity with electron‐poor aryl bromides or heteroaryl bromides. Furthermore, this catalyst can be used at low loading, even for reactions with sterically hindered aryl bromides. The aryl vinyl ether intermediates undergo subsequent ketalisation to give the corresponding 2‐benzyl‐1,3‐dioxolane derivatives.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)