86328-84-9Relevant articles and documents
Highly Regioselective Aromatic C-H Allylation of N-(Arylmethyl)sulfonimides with Allyl Grignard Reagents Involving Benzylic C-N Cleavage
Tian, Shi-Kai,Xie, Dong,Zhu, Meng-Zeng
supporting information, p. 6877 - 6881 (2021/09/11)
A new pair of reaction partners has been established for the aromatic C-H functionalization of benzyl electrophiles with nucleophiles via palladium-catalyzed benzylic C-N cleavage. A range of N-(1-naphthylmethyl)sulfonimides, N-(2-thienylmethyl)sulfonimides, and N-(2-furanylmethyl)sulfonimides smoothly underwent palladium-catalyzed aromatic C-H allylation with allyl Grignard reagents at room temperature, delivering structurally diverse substituted 1-allylnaphthalenes and 2-allylheteroarenes in moderate to excellent yields with extremely high regioselectivities. Replacing the N-(arylmethyl)sulfonimide with an (arylmethyl)ammonium salt, an arylmethyl chloride, or an arylmethyl phosphate as the benzyl electrophile leads to a dramatic erosion of the regioselectivity.
Diiodine-Triethylsilane System: Reduction of N-Sulfonyl Aldimines to N-Alkylsulfonamides
Jiang, Jin,Xiao, Lili,Li, Yu-Long
supporting information, p. 291 - 294 (2020/11/09)
Because molecular iodine and hydrosilanes are stable to both air and moisture, reactions using these reagents are easy to operate and require mild reaction conditions. Molecular iodine and a hydrosilane were used to reduce N-sulfonyl aldimines to the corr
Method for synthesizing N-alkyl sulfonamide in water
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Paragraph 0078; 0079; 0080; 0081; 0082, (2020/12/30)
The invention discloses a method for synthesizing N-alkyl sulfonamide in water, in particular to a method for synthesizing an N-alkyl sulfonamide derivative from a sulfonamide derivative and alcohol,and a water-soluble iridium complex is adopted to catalyze the reaction of N-alkyl sulfonamide. Compared with the previous synthesis method, the method has the advantages that a reaction equivalent substrate is used in the reaction process, so that raw material waste is avoided; weak base is used, and reaction conditions are mild; non-toxic and harmless pure water is used as a solvent in the reaction, only water is generated as a by-product, the atom reaction economy is high, and the requirement of green chemistry is met.
The: N -alkylation of sulfonamides with alcohols in water catalyzed by a water-soluble metal-ligand bifunctional iridium complex [Cp?Ir(biimH2)(H2O)][OTf]2
Ai, Yao,Liu, Pengcheng,Liang, Ran,Liu, Yan,Li, Feng
, p. 10755 - 10762 (2019/07/15)
The iridium complex [Cp?Ir(biimH2)(H2O)][OTf]2 (Cp? = η5-pentamethylcyclopentadienyl, biimH2 = 2,2′-biimidazole) was synthesized and developed as a new-type of water-soluble metal-ligand bifunctional catalyst for the N-alkylation of poorly nucleophilic sulfonamides with alcohols in water. In the presence of catalyst (1 mol%) and Cs2CO3 (0.1 equiv.), a series of desirable products was obtained in 74-91% yields under microwave irradiation. Mechanistic experiments revealed that the presence of NH units in the imidazole ligand is crucially important for the catalytic activity of the iridium complex. Notably, this research would facilitate the process of water-soluble metal-ligand bifunctional catalysis for the hydrogen autotransfer process.
A Gold Carbene Manifold to Prepare Fused γ-Lactams by Oxidative Cyclisation of Ynamides
Sánchez-Cantalejo, Fernando,Priest, Joshua D.,Davies, Paul W.
, p. 17215 - 17219 (2018/11/10)
Gold-catalysed oxidative cyclisation reactions of ynamides offer great promise in γ-lactam synthesis but are limited by preferential over-oxidation to form α-keto imides. Evaluating the factors that might limit N-cyclisation pathways led to effective gold-catalysed conditions that allow access to different fused γ-lactams on changing the ynamide N-substituent and accommodate previously incompatible substitution patterns. New and efficient methods for the synthesis of functionalised 3-aryl indoles and cyclohepta[c]pyrrol-1-one derivatives are presented. These conditions illustrate the complementarity of gold catalysis to other metals.
Enantioselective Synthesis of trans-Vicinal Diamines via Rhodium-Catalyzed [2+2] Cycloaddition of Allenamides
Zheng, Wei-Feng,Sun, Gui-Jun,Chen, Liang,Kang, Qiang
supporting information, p. 1790 - 1794 (2018/04/02)
An efficient protocol for the enantioselective Rh-catalyzed intermolecular head-to-head [2+2] cycloaddition of allenamides was developed. A variety of enantio-enriched cyclobutane-1,2-diamine derivatives were achieved in good yields with good to excellent enantioselectivities. (Figure presented.).
B(C6F5)3-catalyzed transfer hydrogenation of imines and related heteroarenes using cyclohexa-1,4-dienes as a dihydrogen source
Chatterjee, Indranil,Oestreich, Martin
supporting information, p. 1965 - 1968 (2015/02/19)
The strong boron Lewis acid tris(pentafluorophenyl) borane, B(C6F5)3, is shown to abstract a hydride from suitably donor-substituted cyclohexa-1,4-dienes, eventually releasing dihydrogen. This process is coupled with the FLPtype (FLP = frustrated Lewis pair) hydrogenation of imines and nitrogen-containing heteroarenes that are catalyzed by the same Lewis acid. The net reaction is a B(C 6F5)3-catalyzed, i.e., transition-metal-free, transfer hydrogenation using easy-toaccess cyclohexa-1,4-dienes as reducing agents. Competing reaction pathways with or without the involvement of free dihydrogen are discussed.
CuI-catalyzed coupling of gem-dibromovinylanilides and sulfonamides: An efficient method for the synthesis of 2-amidoindoles and indolo[1,2-a] quinazolines
Kiruthika, Selvarangam E.,Perumal, Paramasivan Thirumalai
, p. 484 - 487 (2014/04/03)
A Cu(I)-catalyzed, intermolecular protocol for the synthesis of 2-amidoindoles and tetrahydroindolo[1,2-a]quinazolines in shorter time and high yields is reported. The key highlight of this disclosure is the formation of 2-amidoindole and tetrahydroindolo[1,2-a]quinazoline moieties directly from gem-dibromovinylanilides and sulfonamides in a one-pot fashion through the in situ formation of ynamides followed by a base-promoted intramolecular hydroamidation.
Synthesis of pyrrolo-/indolo[1,2-a ]quinolines and naphtho[2,1- b ]thiophenes from gem -dibromovinyls and sulphonamides
Kiruthika, Selvarangam E.,Nandakumar, Avanashiappan,Perumal, Paramasivan Thirumalai
, p. 4424 - 4427 (2015/02/05)
A highly efficient and simple route for the synthesis of pyrrolo-/indolo[1,2-a]quinolines and naphtho[2,1-b]thiophenes from gem-dibromovinyls and sulphonamides is reported. The noteworthy feature of this report is that the methodology involves a two-step protocol to synthesize tri- and tetracyclic heterocycles in a one-pot fashion through the Cu(I)-catalyzed formation of ynamide followed by a Ag(I)-assisted intramolecular hydroarylation. The photophysical properties of representative examples of pyrrolo- and indolo[1,2-a]quinolines in solid and solution states have also been studied.
Silylium ion promoted reduction of imines with hydrosilanes
Muether, Kristine,Mohr, Jens,Oestreich, Martin
supporting information, p. 6643 - 6646 (2014/01/06)
The silylium ion promoted reduction of imines yielding the corresponding amines is reported. Both tert-butylferrocenylmethylsilane and triethylsilane are efficient hydride donors for the reduction of intermediate silyliminium ions, thereby regenerating th
