3962-43-4Relevant articles and documents
Synthesis of gem-Difluoroalkenes via Nickel-Catalyzed Reductive C-F and C-O Bond Cleavage
Lin, Zhiyang,Lan, Yun,Wang, Chuan
, p. 775 - 780 (2019)
By merging C-O and C-F bond cleavage in cross-electrophile coupling, we developed a method for efficient synthesis of gem-difluoroalkenes with an alkoxy-substituent on the homoallylic position using easily accessible acetals as coupling partners with α-tr
Catalyst-controlled regiodivergent 1,2-difunctionalization of alkenes with two carbon-based electrophiles
Belal, Md.,Li, Zheqi,Yin, Guoyin,Zhu, Lei
, (2021/12/24)
Regiodivergent catalysis provides an efficient strategic approach for the construction of architecturally different molecules from the same starting materials. In this field, the intermolecular regiodivergent 1,2-difunctionalization of alkenes with two electrophiles is still a challenging task. A ligand-controlled, nickel-catalyzed regiodivergent dicarbofunctionalization of alkenes using both aryl/vinyl halides and acetals as electrophiles under mild reductive reaction conditions has been accomplished. This study provides a general approach to accessing both β-methoxyl esters and γ-methoxyl esters from readily available acrylates, aryl halides and acetals. Experimental mechanistic evidence supports that the difference in regioselective outcomes is attributed to the ligand tuning the reactivity of the nickel catalyst, which results in different catalytic cycles operating for these two reaction conditions.
Conjugate addition of acetal-derived benzyl radicals generated from low-valent titanium-mediated CO bond cleavage
Suga, Takuya,Nakamura, Masaharu,Takada, Ryusei,Ukaji, Yutaka
, p. 1258 - 1260 (2021/05/17)
A new method for the generation of benzyl radicals from acetals via low-valent titanium-mediated homolytic CO bond cleavage is presented. The low cost and availability of the developed titanium reagent enable efficient access to α-alkoxy carbon radical species via the developed reaction.
Nondirecting Group sp3 C?H Activation for Synthesis of Bibenzyls via Homo-coupling as Catalyzed by Reduced Graphene Oxide Supported PtPd@Pt Porous Nanospheres
Wang, Zheng-Jun,Lv, Jing-Jing,Yi, Rong-Nan,Xiao, Min,Feng, Jiu-Ju,Liang, Zhi-Wu,Wang, Ai-Jun,Xu, Xinhua
supporting information, p. 932 - 941 (2018/01/05)
The use of heterogeneous bimetallic Pd-based nanocatalyst for directing the inactivated sp3 C?H coupling has been scarcely explored. This work reported the formation of symmetrical C?C bonds from the inactivated sp3 C?H bonds catalyzed by employing reduced graphene oxide supported PtPd@Pt porous nanospheres. The reaction of sp3 C?H activation proceeded under mild conditions without any solvent, ligand or directing group. It is a higher atom-, step- and cost-effectiveness strategy for developing heterogeneous catalysts in the synthesis of bibenzyls with various functional groups (e. g. aryl, alkyl, methoxyl, halogen, ester, and pyridyl). (Figure presented.).
A chiral ligand mediated aza-conjugate addition strategy for the enantioselective synthesis of β-amino esters that contain hydrogenolytically sensitive functionality
Archer, Robert M.,Hutchby, Marc,Winn, Caroline L.,Fossey, John S.,Bull, Steven D.
, p. 8838 - 8847 (2015/10/20)
Aza-conjugate addition of the lithium anion of N-trimethylsilyl-p-methoxybenzylamine to tert-butyl enoate acceptors, in the presence of a stoichiometric amount of enantiopure 1,2-dimethoxy-1,2-diphenylethane and excess trimethylsilyl chloride, affords ter
Catalytic asymmetric bromine-lithium exchange: A new tool to build axial chirality
Perron, Quentin,Alexakis, Alexandre
supporting information; experimental part, p. 2611 - 2620 (2011/01/05)
We present here the first catalytic desymmetrization of the 2,2′,6,6′-tetrabromobiphenyl 1 and analogues, by a bromine-lithium exchange catalyzed by either diamines or diether derivatives (0.5 equiv.), yielding axially chiral compounds in high yield (up to 89%) and high enantioselectivity (up to 82%).
Reductive coupling of aromatic dialkyl acetals using the combination of zinc and chlorotrimethylsilane in the presence of potassium carbonate
Hatano, Bunpei,Nagahashi, Keita,Habaue, Shigeki
, p. 1418 - 1419 (2008/03/14)
The treatment of aromatic acetals with zinc and chlorosilane in the presence of potassium carbonate in toluene brought about facile and effective reductive coupling to give the corresponding coupling products. Copyright
Construction of electrocatalytic electrodes bearing the triphenylamine nucleus covalently bound to carbon. A halogen dance in protonated aminotriphenylamines
Mayers, Brian T.,Fry, Albert J.
, p. 411 - 414 (2007/10/03)
The triarylamine nucleus has been attached to a carbon fiber electrode by diazotization of an aminotriphenylamine followed by electrochemical reduction. The resulting electrodes can electrocatalyze the oxidation of organic substrates. In acid, 4-amino-4′,4″-dibromotriphenylamine undergoes dismutation into a mixture of amines containing from 0 to 3 bromine atoms.
Synthesis and chemistry of enantiomerically pure 10,11-dihydrodibenzo[b,f] thiepines
Wyatt, Paul,Hudson, Andrew,Charmant, Jonathan,Orpen, A. Guy,Phetmung, Hirihattaya
, p. 2218 - 2232 (2008/02/04)
Several chiral thiepines were efficiently constructed using sulfur diimidazole in combination with a variety of bislithiated carbon fragments. The sulfur atom in these thiepines is found to be unusually unreactive compared to diphenylsulfide. The Royal Society of Chemistry 2006.