22920-33-8Relevant articles and documents
One-pot palladium-catalyzed highly chemo-, regio-, and stereoselective synthesis of trans-stilbene derivatives. A concise and convenient synthesis of resveratrol
Jeffery, Tuyet,Ferber, Beno?t
, p. 193 - 197 (2003)
A convenient, efficient and highly chemo-, regio-, and stereoselective one-flask synthetic method is reported for the construction of unsymmetrical (or symmetrical) trans-stilbene derivatives based on two sequential Heck-type reactions using tetraalkylammonium salt-based catalyst systems and vinyltrimethylsilane as double bond equivalents. Resveratrol has thus been concisely synthesized.
Palladium-catalyzed desulfitative mizoroki-heck couplings of sulfonyl chlorides with mono-and disubstituted olefins: Rhodium-catalyzed desulfitative heck-type reactions under phosphine- And base-free conditions
Dubbaka, Srinivas Reddy,Vogel, Pierre
, p. 2633 - 2641 (2007/10/03)
New conditions have been found for the desulfitative Mizoroki-Heck arylation and trifluoromethylation of mono- and disubustituted olefins with arenesulfonyl and trifluoro-methanesulfonyl chlorides. Thus (E)-1,2- disubstituted alkenes with high ster-eoselectivity and 1,1,2-disubstituted alkenes with 12:1 to 21:1 E/Z steroselectivity can be obtained. Herrmann's palladacycle at 0.1 mol% is sufficient to catalyze these reactions, for which electron-rich or electron-poor sulfonyl chlorides and alkenes are suitable. If phosphine- and base-free conditions are required. 1 mol% [RriCl(C 2,H4)2] catalyzes the desulfitative cross-cou pling reactions. Contrary to results reported for [RuCl2(PPh 3)2]-catalyzed coupling reactions with sulfonyl chlorides, the palladium and rhodium desulfitative Mizoroki-Heck coupling reactions are not inhibited by radical scavenging agents. Possible sulfones arising from the sulfonylation of alkenes at 60°C are not desulfitated at higher temperatures in the presence of the Pd or Rh catalysts.