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Palladium‐Catalyzed 1,2‐Addition of Organic Halides and Terminal Alkynes to 7‐Oxabenzonorbornadiene: An Efficient Route to Polyaromatic Hydrocarbons
Author(s) -
Kuo ChunJung,
Cheng ShuJin,
Chang ShuTing,
Liu CharngHsing
Publication year - 2008
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.200700772
Subject(s) - chemistry , halide , palladium , catalysis , organic chemistry , coupling reaction , polymer chemistry , combinatorial chemistry
Abstract A three‐component coupling reaction of organic halides with oxabicyclic alkenes and terminal alkynes was catalyzed by a palladium complex and a phase‐transfer agent in the presence of aqueous NaOH. The reaction gave a series of 5,6‐disubstituated 7‐oxabenzonorbornene derivatives in good yields. The disubstituted products from oxabenzonorbornadiene can be readily converted into polyaromatic hydrocarbons by a Lewis acid mediated deoxyaromatization reaction. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)