953780-85-3Relevant academic research and scientific papers
Direct palladium/carboxylic acid-catalyzed C-allylation of cyclic 1,3-diones with allylic alcohols in water
Gan, Kim-Hong,Jhong, Ciou-Jyu,Yang, Shyh-Chyun
, p. 1204 - 1212 (2008/09/17)
The direct activation of C-O bonds in allylic alcohols in water as a suspension medium by palladium complexes has been accelerated by carrying out the reactions in the presence of a carboxylic acid. The palladium-catalyzed allylation of cyclic 1,3-diones using allylic alcohols directly gave the corresponding C-allylated products in good yields.
Oxygen donor-mediated equilibration of diastereomeric alkene-palladium(II) intermediates in enantioselective desymmetrizing heck cyclizations
Machotta, Axel B.,Straub, Bernd F.,Oestreich, Martin
, p. 13455 - 13463 (2008/09/17)
This investigation examines the origin of enantioselection in the desymmetrization of an acyclic prochiral Heck cyclization precursor. High asymmetric induction (97-98% ee) is attributed to a temporary interaction of a Lewis basic oxygen donor with weakly Lewis acidic palladium(II). A series of control experiments combined with quantum-chemical model calculations provided sound evidence for a mechanism involving oxygen donor-mediated, rapid equilibration of diastereomeric alkene-palladium(II) complexes prior to the selectivity-determining ring-closing event, a Curtin-Hammett scenario. Our study also highlights the importance of the cationic pathway (triflate counter anions versus halido ligand) and alkene stereochemistry (E versus Z) in asymmetric Heck reactions.
Et3B-promoted, Pd-catalyzed C-allylation of o-hydroxyacetophenone and its derivatives with allyl alcohols
Horino, Yoshikazu,Naito, Makoto,Kimura, Masanari,Tanaka, Shuji,Tamaru, Yoshinao
, p. 3113 - 3116 (2007/10/03)
Triethylborane promotes the Pd-catalyzed selective C-diallylation of o-hydroxyacetophenone and C-monoallylation of o-hydroxypropiophenone with a variety of ally alcohols. The reaction proceeds smoothly at 25-50°C and provides the allylation products in excellent yields.
