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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 28, Number 7
BKCSDE 28(7)
July 20, 2007 

Parallel Synthesis of Unsymmetrical trans-Stilbenes
Chul-Hee Cho, Kwangyong Park*
Unsymmetrical trans-stilbenes, Stilbenesulfonates, Nickel-catalyst, Cross-coupling
New unsymmetrical trans-stilbenes have been prepared by the sequential coupling reactions of bromobenzenesulfonate with formylarylboronic acids, benzylphosphonates and arylmagnesium bromides and characterized. The nickel-catalyzed reactions of stilbenesulfonates with aryl Grignard reagents produced the corresponding stilbenes via the nucleophilic aromatic substitution of the neopentyloxysulfonyl group by aryl nucleophiles. The great chemoselectivity of the alkyloxysulfonyl group allows the stepwise construction of unsymmetrical trans-stilbenes possessing terphenyl moieties. This procedure appears to be a promising and conceptually straightforward route for the parallel synthesis of various unsymmetrical stilbenes as well as other highly conjugated hydrocarbons.
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