39491-73-1Relevant academic research and scientific papers
Unprecedented elimination of conjugated phenylthioether groups by low-valent titanocene
Ribeiro, Nigel,Fetzer, Ludivine,Streiff, Stéphane,Désaubry, Laurent
, p. 2928 - 2930 (2010)
The first thioether elimination reaction utilizing a low-valent titanocene has been discovered. This reaction occurs under mild conditions and affords stereospecifically a variety of dienes and styrenes. Our data suggest that this new reaction involves an
Contra-Thermodynamic Positional Isomerization of Olefins
Zhao, Kuo,Knowles, Robert R.
supporting information, p. 137 - 144 (2022/01/19)
A light-driven method for the contra-thermodynamic positional isomerization of olefins is described. In this work, stepwise PCET activation of a more substituted and more thermodynamically stable olefin substrate is mediated by an excited-state oxidant an
Divergent Reactivity of α,α-Disubstituted Alkenyl Hydrazones: Bench Stable Cyclopropylcarbinyl Equivalents
Ritchie, Nina F. C.,Zahara, Adam J.,Wilkerson-Hill, Sidney M.
supporting information, p. 2101 - 2106 (2022/02/14)
Herein we report the divergent reactivity of 2,2-dialkyl-3-(E)-alkenyl N-tosylhydrazones using Pd-catalyzed cross-coupling conditions, which enable the Z-selective synthesis of 3-aryl-1,4-dienes and gem-dialkyl vinylcyclopropanes. We found that the dialky
Gold-catalyzed [4+2] Annulations of Dienes with Nitrosoarenes as 4 π Donors: Nitroso-Povarov Reactions
Chen, Ching-Nung,Liu, Rai-Shung
, p. 9831 - 9835 (2019/07/04)
This work reports the first success of the nitroso-Povarov reaction, involving gold-catalyzed [4+2] annulations of nitrsoarenes with substituted cyclopentadienes. In this catalytic sequence, nitrosoarenes presumably attack gold-π-dienes by a 1,4-addition pathway, generating allylgold nitrosonium intermediates to complete an intramolecular cyclization. Acyclic dienes are also applicable substrates, and affording oxidative nitroso-Povarov products.
Nickel-Catalyzed system for the cross-coupling of alkenyl methyl ethers with grignard reagents under mild conditions
Hostier, Thomas,Neouchy, Zeina,Ferey, Vincent,Gomez Pardo, Domingo,Cossy, Janine
supporting information, p. 1815 - 1818 (2018/04/14)
A nickel-catalyzed cross-coupling of alkenyl methyl ethers with Grignard reagents, under mild conditions, is described. These conditions allowed access to various stilbenes and heterocyclic stilbenic derivatives as well as to a potential anticancer agent DMU-212.
Transition-metal-free synthesis of vicinal triborated compounds and selective functionalisation of the internal C-B bond
Davenport, Elliot,Fernandez, Elena
supporting information, p. 10104 - 10107 (2018/09/18)
1,2,3-Triborated compounds can be prepared by simple nucleophilic borylation of 1,3-dienes, without the assistance of metal catalysts. Selective functionalisation of the internal C-B bond of the 1,2,3-triborated compounds, through cross-coupling with aryl
Solvate Ionic Liquids as Reaction Media for Electrocyclic Transformations
Eyckens, Daniel J.,Champion, Megan E.,Fox, Bronwyn L.,Yoganantharajah, Prusothman,Gibert, Yann,Welton, Tom,Henderson, Luke C.
supporting information, p. 913 - 917 (2016/03/01)
Solvate ionic liquids (SILs) consisting of lithium bis(trifluoromethylsulfonyl)imide dissolved in tri-or tetraglyme have recently emerged as a novel class of ionic liquids. Herein, the first use of solvate ionic liquids as a replacement for molecular solvents in electrocyclization reactions is reported. The SILs promoted both Diels-Alder and [2+2] cycloaddition reactions, compared to an appropriate molecular solvent, and 5 M lithium perchlorate in diethyl ether. The Gutmann acceptor number (AN) of these solvate ionic liquids has also been determined by 31P NMR spectroscopy to be 26.5, thus being modest Lewis acids.
Copper(I)-catalyzed alkylation of aryl- and alkenylsilanes activated by intramolecular coordination of an alkoxide
Tsubouchi, Akira,Muramatsu, Daisuke,Takeda, Takeshi
, p. 12719 - 12722 (2013/12/04)
Let's coordinate: Copper(I)-catalyzed cross-coupling of alkenyl- and arylsilanes with primary alkyl iodides as well as allylic and benzylic halides as C(sp3)-X electrophilic coupling partners has been realized by intramolecular activation through alkoxide coordination. This alkylation tolerates a range of functional groups including a free hydroxy group. IPr=1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene. Copyright
Stereoselective synthesis of 1,3-dienes from propargylic alcohols by LiAlH4/AlCl3
Cui, Dong-Mei,Zhu, Kai,Chen, Li,Qi, Lang-Jun,Zhang, Cheng-Zhu,Zheng, Chen
supporting information, p. 2380 - 2384 (2013/07/26)
Herein we report that LiAlH4/AlCl3 is a very efficient reagent for the reductive dehydration of aryl propargylic alcohols in tetrahydrofuran solvent at reflux to give 1,3-dienes with good yields and high E selection. The reaction con
Palladium-catalyzed allylic fluorination of cinnamyl phosphorothioate esters
Lauer, Andrew M.,Wu, Jimmy
supporting information, p. 5138 - 5141,4 (2012/12/12)
A highly regioselective, Pd-catalyzed allylic fluorination of phosphorothioate esters is reported. This chemistry addresses several limitations of previously reported methods in which elimination and lack of reactivity were problematic. Preliminary mechanistic investigations reveal that these reactions are stereospecific and provide fluorinated products with net retention of stereochemical configuration. In analogy to other Pd-catalyzed allylic substitution reactions, this process likely proceeds through a palladium π-allyl intermediate.
