84192-53-0Relevant academic research and scientific papers
Ni/Photoredox-Catalyzed Enantioselective Cross-Electrophile Coupling of Styrene Oxides with Aryl Iodides
Lau, Sii Hong,Borden, Meredith A.,Steiman, Talia J.,Wang, Lucy S.,Parasram, Marvin,Doyle, Abigail G.
supporting information, p. 15873 - 15881 (2021/10/12)
A Ni/photoredox-catalyzed enantioselective reductive coupling of styrene oxides and aryl iodides is reported. This reaction affords access to enantioenriched 2,2-diarylalcohols from racemic epoxides via a stereoconvergent mechanism. Multivariate linear regression (MVLR) analysis with 29 bioxazoline (BiOx) and biimidazoline (BiIm) ligands revealed that enantioselectivity correlates with electronic properties of the ligands, with more electron-donating ligands affording higher ee's. Experimental and computational mechanistic studies were conducted, lending support to the hypothesis that reductive elimination is enantiodetermining and the electronic character of the ligands influences the enantioselectivity by altering the position of the transition state structure along the reaction coordinate. This study demonstrates the benefits of utilizing statistical modeling as a platform for mechanistic understanding and provides new insight into an emerging class of chiral ligands for stereoconvergent Ni and Ni/photoredox cross-coupling.
Tetraphenylphosphonium Tetrafluoroborate/1,1,1,3,3,3-Hexafluoroisopropanol (Ph4PBF4/HFIP) Effecting Epoxide-Initiated Cation-Olefin Polycyclizations
Tian, Yan,Xu, Xin,Zhang, Lin,Qu, Jin
, p. 268 - 271 (2016/02/03)
The use of an excess amount of tetraphenylphosphonium tetrafluoroborate in 1,1,1,3,3,3-hexafluoroisopropanol, which can stabilize the intermediate cation in the reaction, efficiently promoted epoxide-initiated cation-olefin polycyclization reactions with broad functional group tolerance and water and oxygen tolerance.
Weinreb amide based building blocks for convenient access to 1,1-diarylethenes and isocombretastatin analogues
Balasubramaniam, Sivaraman,Kommidi, Harikrishna,Aidhen, Indrapal Singh
supporting information; experimental part, p. 2683 - 2686 (2011/06/19)
A successful strategy based on the synthetic equivalent containing Weinreb amide functionality for the convenient access to 1,1-diarylethenes in general and for the isocombretastatin analogues in particular has been developed from the commercially available glyoxalic acid. The convenience with which the structural variations can be made in assembling the aryl residues shows generality associated with the developed strategy. The intermediates also provide access to 1,2,2-triarylethanones, represented by the synthesis of advanced intermediate of tamoxifen.
Friedel-Crafts alkylation of arenes with epoxides promoted by fluorinated alcohols or water
Li, Guo-Xing,Qu, Jin
supporting information; experimental part, p. 2653 - 2655 (2010/07/08)
The stereoselective intra- and intermolecular Friedel-Crafts alkylation of electron-rich arenes with epoxides can take place in refluxing 1,1,1,3,3,3-hexafluoroisopropanol owing to its weak acidity and high ionizing power.
1-(N,N-diisopropylcarbamoyloxy)-1-tosyl-1-alkenes - a2d 1 synthons via tandem umpolung
Chen, Yue-Lei,Hoppe, Dieter
supporting information; experimental part, p. 4188 - 4194 (2009/09/25)
(Equation Presented) 1-(N,N-Diisopropylcarbamoyloxy)-1-tosyl-alkenes have been developed as an a2d1 synthon via tandem umpolung. Upon addition of Grignard reagents and further quench by carbonyl compounds, this synthon produces α,α′-
Molybdenum-catalyzed aromatic substitution with olefins and alcohols
Shimizu, Isao,Khien, Kuok Meng,Nagatomo, Miki,Nakajima, Takayuki,Yamamoto, Akio
, p. 851 - 852 (2007/10/03)
A new type of electrophilic aromatic substitution without using organic halides has been realized by using Mo(CO)6 catalyst.
The effect of meta- and para-methoxy substitution on the reactivity of the radical cations of arylalkenes and alkanes. Radical ions in photochemistry. Part 26
Arnold, Donald R.,Du, Xinyao,Henseleit, Kerstin M.
, p. 839 - 852 (2007/10/02)
The effect of meta- and para-methoxy substitution on the reactivity of some radical cations has been determined.The compounds chosen for study were 1-(3-methoxyphenyl)-1-phenylethylene (7), 1-(4-methoxyphenyl)-1-phenylethylene (8), 3-(3-methoxyphenyl)inde
A Comparison of Some Friedel-Crafts and Grignard Reactions of Optically Active Phenyloxirane
Taylor, Stephen K.,Haberkamp, William C.,Brooks, Dee W.,Whittern, David N.
, p. 1745 - 1747 (2007/10/02)
The Friedel-Crafts reactions of optically active phenyloxirane with toluene and anisole were examined for stereospecifity.The enantiomeric ratios of the diarylethanol products were determined and compared to those of the same products obtained from the reaction of p-tolyl and p-methoxyphenyl Grignard reagents with optically active phenyloxirane.The p-tolyl Grignard and Friedel-Crafts products gave similar enantiomeric ratios (approximately 64:36 and 60:40, respectively).However, in the p-methoxyphenyl products from the Grignard and Friedel-Crafts reactions, different enantiomers predominated (ratios 33:67 and 62:38, respectively).
