95435-84-0Relevant articles and documents
Synthesis and biological evaluation of 3-(Prop-2-enyl)- and 3-(Prop-2-ynyl)pyrrolidine-2,5-dione derivatives as potential aromatase inhibitors
Barrell,Woo,Ahmadi,Smith,Nicholls
, p. 154 - 159 (1996)
3-(4'-Aminophenyl)pyrrolidine-2,5-dione (WSP3), a known reversible inhibitor of P450 aromatase, was modified using molecular graphics and our model of reversible inhibitor and substrate binding to resemble 10β-prop-2-ynylestr-4-ene-3,17-dione (PED), a mec
Palladium-catalyzed cross-coupling reaction of sulfoxonium ylides and benzyl bromides by carbene migratory insertion
Yan, Kaichuan,He, Maoyao,Li, Jianglian,He, Hua,Lai, Ruizhi,Luo, Yi,Guo, Li,Wu, Yong
supporting information, p. 14287 - 14290 (2020/11/24)
A palladium-catalyzed cross-coupling reaction of sulfoxonium ylides and benzyl bromides has been developed, which has potential safety advantages over previous carbene coupling reactions using either diazo compounds or their in situ precursors. This reaction affords polysubstituted olefins, and features good substrate tolerance and is suitable for late-stage modification of biologically active molecules. Pd-carbene migratory insertion is supposed to be involved in this coupling reaction.
Rapid Bis-Coupling Reactivity with Triarylbismuth Reagents: Synthesis of Structurally Diverse Scaffolds and Step-economic Convergent Synthesis of Quebecol
Rao, Maddali L. N.,Murty, Venneti N.,Nand, Sachchida
, p. 1629 - 1636 (2020/03/05)
The cross-coupling study of gem-dibromoesters with triarylbismuths as threefold arylating reagents was investigated under palladium-catalyzed conditions. This study using triarylbismuth reagents explored the cross-coupling reactivity with various functionalized gem-dibromoesters. It furnished a variety of multi-functional trisubstituted acrylates embedded with aryl, alkene and alkyne scaffolds in high yields. The present study in turn, provided easy access to various triarylated acrylates and functionalized 1,3-dienyl and 1,3-enyne esters. Further, the established method applied in the step-economic and convergent synthesis of quebecol natural product in good yield.
Preparation of 2,3,3-Triarylacrylic Acid Esters Using Suzuki-Miyaura Coupling Reactions
Cardinal, Sébastien,Voyer, Normand
, p. 1202 - 1216 (2016/05/11)
We report here a new strategy to produce 2,3,3-triarylacrylic acid esters, a class of 1,2,2-triarylethene compounds with an α,β-unsaturated ester functionality. Our approach requires the preparation of a gem-dibromoalkene precursor from an α-keto ester, followed by the installation of two aryl groups by Suzuki-Miyaura coupling reactions on the two C-Br bonds. Many 2,3,3-triarylacrylic acid esters with one, two, or three different aryl groups were obtained with complete regio- and stereocontrol in most cases.
Rearrangement Reactions of Tritylcarbenes: Surprising Ring Expansion and Computational Investigation
Banert, Klaus,Hagedorn, Manfred,Pester, Tom,Siebert, Nicole,Staude, Cornelius,Tchernook, Ivan,Rathmann, Katharina,Holl?czki, Oldamur,Friedrich, Joachim
, p. 14911 - 14923 (2015/10/19)
As a rule, acetylides and sulfonyl azides do not undergo electrophilic azide transfer because 1,2,3-triazoles are usually formed. We show now that treatment of tritylethyne with butyllithium followed by exposure to 2,4,6-triisopropylbenzenesulfonyl azide leads to products that are easily explained through the generation of short-lived tritylethynyl azide and its secondary product cyanotritylcarbene. Furthermore, it is demonstrated that tritylcarbenes generally do not produce triphenylethenes exclusively, as was stated in the literature. Instead, these carbenes always yielded also (diphenylmethylidene)cycloheptatrienes (heptafulvenes) as side products. This result is supported by static DFT, coupled cluster, and ab initio molecular dynamics calculations. From these investigations, the fused bicyclobutane intermediate was found to be essential for heptafulvene formation. Although the bicyclobutane is also capable of rearranging to the triphenylethene product, only the heptafulvene pathway is reasonable from the energetics. The ethene is formed straight from cyanotritylcarbene.
Toward waste-free production of heck products with a catalytic palladium system under oxygen
Dams, Mieke,De Vos, Dirk E.,Celen, Sofie,Jacobs, Pierre A.
, p. 3512 - 3515 (2007/10/03)
A 100% carbon-efficient, halide- and solvent-free alternative for the synthesis of Heck-type products is the direct oxidative coupling of arenes with olefins, catalyzed by Pd(OAc)2 under oxygen (see scheme). The reactions can be performed under mild conditions, and water is the only by-product. (TON = turnover number, TOF = turnover frequency.).
