58287-15-3Relevant academic research and scientific papers
Organocatalytic asymmetric synthesis of 1,1-diarylethanes by transfer hydrogenation
Wang, Zhaobin,Ai, Fujin,Wang, Zheng,Zhao, Wanxiang,Zhu, Guangyu,Lin, Zhenyang,Sun, Jianwei
supporting information, p. 383 - 389 (2015/01/30)
A new organocatalytic transfer hydrogenation strategy for the asymmetric synthesis of 1,1-diarylethanes is described. Under mild conditions, a range of 1,1-diarylethanes substituted with an o-hydroxyphenyl or indole unit could be obtained with excellent efficiency and enantioselectivity. We also extended the protocol to an unprecedented asymmetric hydroarylation of 1,1-diarylalkenes with indoles for the synthesis of a range of highly enantioenriched 1,1,1-triarylethanes bearing acyclic all-carbon quaternary stereocenters. These diaryl- and triarylethanes exhibit impressive cytotoxicity against a number of human cancer cell lines. Preliminary mechanistic studies combined with DFT calculations provided important insight into the reaction mechanism.
Pd(0)-catalyzed 1,1-diarylation of ethylene and allylic carbonates
Saini, Vaneet,Liao, Longyan,Wang, Qiaofeng,Jana, Ranjan,Sigman, Matthew S.
supporting information, p. 5008 - 5011 (2013/10/22)
An efficient protocol for the one-step synthesis of biologically relevant 1,1-diarylalkanes has been described. This reaction introduces two different aryl groups across the terminal end of simple feedstock alkenes such as ethylene and allylic carbonates.
Niobium(V) pentachloride: an efficient catalyst for C-, N-, O-, and S-nucleophilic substitution reactions of benzylic alcohols
Yadav,Bhunia, Dinesh C.,Vamshi Krishna,Srihari
, p. 8306 - 8310 (2008/03/30)
Benzylic alcohols undergo easy C-, N-, O-, and S- centered nucleophilic substitution reactions with a catalytic amount of NbCl5.
Kinetic and Thermodynamic Barriers to Carbon and Oxygen Alkylation of Phenol and Phenoxide Ion by the 1-(4-Methoxyphenyl)ethyl Carbocation
Tsuji, Yutaka,Toteva, Maria M.,Garth, Heather A.,Richard, John P.
, p. 15455 - 15465 (2007/10/03)
Rate constant ratios for addition of the three nucleophilic sites of phenol to the 1-(4-methoxyphenyl)ethyl carbocation (1+) in 50/50 (v/v) trifluoroethanol/water were determined from the relative yields of the three phenol adducts, and absolute rate constants were determined from product rate constant ratios for addition of phenol and azide ion to 1+ using kaz = 5 × 109 M-1 s-1 for the diffusion-limited reaction of azide ion. A selectivity of 230:20:1 was determined for alkylation of phenol at oxygen, C-4 and C-2 to form 1-OPh and biphenyls 1-(4-C6H4OH) and 1-(2-C6H 4OH), respectively, and of 2:2:1 for alkylation of the corresponding nucleophilic sites of phenoxide ion in diffusion-limited reactions. The Mayr nucleophilicity parameter for C-4 of phenol is N = 2.0. Encounter-limited addition of phenoxide ion to 1+ to form 1-OPh is faster than encounter-limited addition of oxygen anions that are either more or less basic than phenoxide ion. Only the products of solvolysis are observed from acid-catalyzed cleavage of 1-OPh in 50/50 (v/v) trifluoroethanol/water, but a 50% yield of biphenyls 1-(4-C6H4OH) and 1-(2-C 6H4OH) are observed from spontaneous cleavage of 1-OPh, where the leaving group is phenoxide ion, because of the very low kinetic barriers to collapse of the ion pair intermediate 1+.PhO -. The 230-fold larger rate constant for O-compared to C-2-alkylation of phenol is due primarily to the larger thermodynamic driving force for oxygen addition. There are similar Marcus intrinsic barriers for these two reactions.
Trialkylsilyloxy-1,1-diphenyl ethylenes and polymers produced therewith
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, (2008/06/13)
Trialkylsilyloxy-1,1-diphenyl ethylenes corresponding to general formula I, new polymers produced therewith terminated by aryl trialkylsilyl ether groups or by phenolic hydroxyl groups and a process for the production of these polymers by anionic polymeri
