64277-35-6Relevant academic research and scientific papers
Palladium-Catalyzed Conjugate Addition of Arylboronic Acids to β,β-Disubstituted Enones in Aqueous Media: Formation of Bis-benzylic and ortho-Substituted Benzylic Quaternary Centers
Van Zeeland, Ryan,Stanley, Levi M.
, p. 5203 - 5206 (2015/09/15)
Palladium-catalyzed conjugate addition of arylboronic acids to β,β-disubstituted enones in aqueous media is reported. Additions of a wide range of arylboronic acids to β,β-disubstituted enones occur to form ketone products bearing benzylic all-carbon quaternary centers. These reactions are promoted by a simple catalyst prepared from palladium trifluoracetate and 2,2′-bipyridine. The use of aqueous sodium trifluoracetate as the reaction medium significantly enhances reactivity and enables the formation of challenging bis-benzylic and ortho-substituted benzylic all-carbon quaternary centers.
Synthesis of diverse β-quaternary ketones via palladium-catalyzed asymmetric conjugate addition of arylboronic acids to cyclic enones
Holder, Jeffrey C.,Goodman, Emmett D.,Kikushima, Kotaro,Gatti, Michele,Marziale, Alexander N.,Stoltz, Brian M.
, p. 5781 - 5792 (2015/08/03)
Abstract The development and optimization of a palladium-catalyzed asymmetric conjugate addition of arylboronic acids to cyclic enone conjugate acceptors is described. These reactions employ air-stable and readily-available reagents in an operationally si
Efficient formation of benzylic quaternary centers via palladium catalysis
Gottumukkala, Aditya L.,Suljagic, Jasmin,Matcha, Kiran,De Vries, Johannes G.,Minnaard, Adriaan J.
, p. 1636 - 1639 (2013/10/21)
Four's a crowd: An efficient protocol for the formation of benzylic quaternary centers via arylation of enones using a catalyst made from Pd(O 2CCF3)2 and 2,2′-bipyridine is developed. For cyclic substrates, catalyst loadi
Palladium-catalyzed asymmetric quaternary stereocenter formation
Gottumukkala, Aditya L.,Matcha, Kiran,Lutz, Martin,De Vries, Johannes G.,Minnaard, Adriaan J.
supporting information; experimental part, p. 6907 - 6914 (2012/07/01)
An efficient palladium catalyst is presented for the formation of benzylic quaternary stereocenters by conjugate addition of arylboronic acids to a variety of β,β-disubstituted carbocyclic, heterocyclic, and acyclic enones. The catalyst is readily prepared from PdCl2, PhBOX, and AgSbF 6, and provides products in up to 99 % enantiomeric excess, with good yields. Based on this strategy, (-)-α-cuparenone has been prepared in only two steps. Copyright
Palladium-catalyzed asymmetric conjugate addition of arylboronic acids to five-, six-, and seven-membered β-substituted cyclic enones: enantioselective construction of all-carbon quaternary stereocenters
Kikushima, Kotaro,Holder, Jeffrey C.,Gatti, Michele,Stoltz, Brian M.
supporting information; experimental part, p. 6902 - 6905 (2011/06/19)
The first enantioselective Pd-catalyzed construction of all-carbon quaternary stereocenters via 1,4-addition of arylboronic acids to β-substituted cyclic enones is reported. Reaction of a wide range of arylboronic acids and cyclic enones using a catalyst
