389-42-4Relevant academic research and scientific papers
Photoinduced Hydroarylation and Cyclization of Alkenes with Luminescent Platinum(II) Complexes
Cheng, Hanchao,Lam, Tsz-Lung,Liu, Yungen,Tang, Zhou,Che, Chi-Ming
supporting information, p. 1383 - 1389 (2020/11/30)
Photoinduced hydroarylation of alkenes is an appealing synthetic strategy for arene functionalization. Herein, we demonstrated that aryl radicals generated from electron-deficient aryl chlorides/bromides could be trapped by an array of terminal/internal aryl alkenes in the presence of [Pt(O^N^C^N)] under visible-light (410 nm) irradiation, affording anti-Markovnikov hydroarylated compounds in up to 95 % yield. Besides, a protocol for [Pt(O^N^C^N)]-catalyzed intramolecular photocyclization of acrylanilides to give structurally diverse 3,4-dihydroquinolinones has been developed.
Fluorinations of unsymmetrical diaryliodonium salts containing: Ortho -sidearms; Influence of sidearm on selectivity
Abudken, Ahmed M. H.,Hope, Eric G.,Singh, Kuldip,Stuart, Alison M.
, p. 6140 - 6146 (2020/10/30)
Activated aromatics were reacted with two different fluoroidoane reagents 1 and 2 in the presence of triflic acid to prepare only the para-substituted diaryliodonium salts. With fluoroiodane 1 the unsymmetrical diaryliodonium salts contained an ortho-propan-2-ol sidearm, whereas the alcohol sidearm was eliminated to form an ortho-styrene sidearm in the reaction with fluoroiodane 2. Only the diaryliodonium salts containing a styrene sidearm were fluorinated successfully to deliver para-fluorinated aromatics in good yields.
Br?nsted Acid Catalyzed Peterson Olefinations
Britten, Thomas K.,McLaughlin, Mark G.
, p. 301 - 305 (2019/12/25)
A mild and facile Peterson olefination has been developed employing low catalyst loading of the Br?nsted acid HNTf2. The reactions are typically performed at room temperature, with the reaction tolerant to a range of useful functionalities. Furthermore, we have extended this methodology to the synthesis of enynes.
Cu/Ni-Catalyzed Cyanomethylation of Alkenes with Acetonitrile for the Synthesis of β,γ-Unsaturated Nitriles
Jian, Hong,Shen, Zengming,Zhang, Saisai
, p. 6143 - 6150 (2020/05/22)
We have developed a protocol for the Cu/Ni-catalyzed cyanomethylation of alkenes with acetonitrile for the synthesis of β,γ-unsaturated nitriles. This is the first example of a direct coupling of the alkene sp2 C - H bond and the acetonitrile sp3 C - H bond for the preparation of β,γ-unsaturated nitriles. Acetonitrile, an inexpensive and stable solvent, is demonstrated to be a useful cyanomethyl source. The combination of copper and nickel catalysts resulted in a high reaction efficiency.
Halogenation of 1,1-diarylethylenes by N-halosuccinimides
Zhang, Ge,Bai, Rui-Xue,Li, Chu-Han,Feng, Chen-Guo,Lin, Guo-Qiang
supporting information, p. 1658 - 1662 (2018/12/11)
An efficient method for the preparation of 2,2-diarylvinyl halides from the corresponding 1,1-diarylethylenes has been developed. N-Halosuccinimides (N-bromosuccinimide or N-chlorosuccinimide) were used as the halogenation reagents. The practicability of this method is highlighted by its simple operation, broad substrate scope and capability for large-scale reaction.
Nickel-Catalyzed Direct Synthesis of Aryl Olefins from Ketones and Organoboron Reagents under Neutral Conditions
Lei, Chuanhu,Yip, Yong Jie,Zhou, Jianrong Steve
supporting information, p. 6086 - 6089 (2017/05/08)
Nickel-catalyzed addition of arylboron reagents to ketones results in aryl olefins directly. The neutral condition allows acidic protons of alcohols, phenols, and malonates to be present, and fragile structures are also tolerated.
Electronic polarizability-based stereochemical model for Sharpless AD reactions
Han, Peng,Wang, Ruji,Wang, David Zhigang
supporting information; experimental part, p. 8873 - 8878 (2011/12/02)
Softness really is the hard force! Reported here was the critical yet long-overlooked role of electronic polarizability (i.e., softness) effect in controlling absolute stereochemical courses of general asymmetric induction events. Thus, a sensitive dependence of the sense of chiral induction on an alkene substrate's substituent electronic polarizability character was uncovered from a range of structurally highly comparable Sharpless asymmetric dihydroxylation (AD) systems, from which a new polarizability-based stereochemical model of predictive power was suggested.
Decarbonylative Heck olefination of enol esters: Salt-free and environmentally friendly access to vinyl arenes
Goossen, Lukas J.,Paetzold, Jens
, p. 1095 - 1098 (2007/10/03)
Thank you, no salt on the side. In this variant of the Heck olefination, enol esters serve as environmentally friendly synthetic equivalents of aryl halides. These reactants, in turn, are available from a waste-free synthesis from carboxylic acids and propyne. Thus, a salt-free overall process has been devised for preparing vinyl arenes from a variety of aromatic carboxylic acids.
Pd-catalyzed decarbonylative olefination of aryl esters: Towards a waste-free Heck reaction
Goossen, Lukas J.,Paetzold
, p. 1237 - 1241 (2007/10/03)
Easy and clean: A palladium (0)-catalyzed decarbonylative Heck olefination of activated esters of aryl, heteroaryl, and vinyl carboxylic acids opens up an opportunity for a novel waste-free Heck olefination process (see scheme).
Pd-catalyzed decarbonylative heck olefination of aromatic carboxylic acids activated in situ with di-tert-butyl dicarbonate
Goo?en, Lukas J.,Paetzold, Jens,Winkel, Lars
, p. 1721 - 1723 (2007/10/03)
The first protocol for a direct Heck olefination of aromatic carboxylic acids has been developed. By treatment with commercially available di-tert-butyl dicarbonate, the carboxylic acids are converted in situ into the mixed anhydrides, which in the presen
