139016-12-9Relevant academic research and scientific papers
Synthesis, Characterization, and Reaction of a Both Inter- and Intramolecularly Coordinated Pseudocyclic Iodosylbenzene–Trifluoroacetic Acid Complexes
Yudasaka, Masaharu,Maruyama, Toshifumi,Yamaguchi, Eiji,Tada, Norihiro,Itoh, Akichika
, p. 550 - 556 (2018)
An ortho-substituted ether-oxygen-coordinated pseudocyclic iodosylbenzene-trifluoroacetic acid (pcISB-TFA) complex was synthesized and characterized by X-ray crystallographic analysis. TFA suppresses the disproportionation by both coordination of the oxygen atom to the iodine(III) center through secondary bonding and by hydrogen bonding to the oxygen anion. This bench-stable reagent is highly soluble in common organic solvents and reacts with various organic substrates under mild reaction conditions to give the corresponding products in good yields.
Oxidative Kinetic Resolution of Cyclic Benzylic Ethers
Liu, Lei,Liu, Ziqiang,Ma, Yingang,Sun, Shutao
supporting information, p. 176 - 180 (2020/10/30)
A manganese-catalyzed oxidative kinetic resolution of cyclic benzylic ethers through asymmetric C(sp3)?H oxidation is reported. The practical approach is applicable to a wide range of 1,3-dihydroisobenzofurans bearing diverse functional groups and substituent patterns at the α position with extremely efficient enantiodiscrimination. The generality of the strategy was further demonstrated by efficient oxidative kinetic resolution of another type of five-membered cyclic benzylic ether, 2,3-dihydrobenzofurans, and six-membered 6H-benzo[c]chromenes. Direct late-stage oxidative kinetic resolution of bioactive molecules that are otherwise difficult to access was further explored.
Synthesis of Functionalized Indolines and Dihydrobenzofurans by Iron and Copper Catalyzed Aryl C-N and C-O Bond Formation
Henry, Martyn C.,Senn, Hans Martin,Sutherland, Andrew
, p. 346 - 364 (2019/01/08)
A simple and effective one-pot, two-step intramolecular aryl C-N and C-O bond forming process for the preparation of a wide range of benzo-fused heterocyclic scaffolds using iron and copper catalysis is described. Activated aryl rings were subjected to a highly regioselective, iron(III) triflimide-catalyzed iodination, followed by a copper(I)-catalyzed intramolecular N-or O-arylation step leading to indolines, dihydrobenzofurans, and six-membered analogues. The general applicability and functional group tolerance of this method were exemplified by the total synthesis of the neolignan natural product, (+)-obtusafuran. DFT calculations using Fukui functions were also performed, providing a molecular orbital rationale for the highly regioselective arene iodination process.
Synthesis of Functionalized Dihydrobenzofurans by Direct Aryl C?O Bond Formation under Mild Conditions
Alvarado, Joseph,Fournier, Jeremy,Zakarian, Armen
supporting information, p. 11625 - 11628 (2016/10/24)
A method for the synthesis of dihydrobenzofurans by a direct aryl C?O bond formation is described. A mechanistic pathway for the reaction, distinct from previously described similar transformations, allows for mild reaction conditions that are expected to be compatible with functionalized substrates.
A process for the preparation of benzofuran compounds (by machine translation)
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Paragraph 0078; 0079; 0080; 0081; 0082, (2016/11/17)
The present invention provides a method for the preparation of benzofuran compounds, comprises: under the nitrogen atmosphere, sulfate and organic solvent in the presence of, the three a base silicon group protection of the methoxyphenol compound reaction
Phenol and aniline oxidative coupling with alkenes by using hypervalent iodine dimer for the rapid access to dihydrobenzofurans and indolines
Dohi, Toshifumi,Toyoda, Yosuke,Nakae, Tomofumi,Koseki, Daichi,Kubo, Hiroko,Kamitanaka, Tohru,Kita, Yasuyuki
, p. 631 - 644 (2015/03/04)
A highly reactive hypervalent iodine dimer, [Ph(CF3COO)I]-O- [I(OCOCF3)Ph], is utilized as successful promoter in the oxidative phenolic coupling with styrenes leading to 2-aryldihydrobenzofurans. The extensions of the substrates in this study have led to the development of a new expeditious construction of the pyrroloindoline structure from aniline and enamide derivatives.
Metal-Free [3+2] Oxidative Coupling of Phenols with Alkenes: Synthesis of Dihydrobenzofurans
Zhao, Yating,Huang, Binbin,Yang, Chao,Li, Bing,Xia, Wujiong
supporting information, p. 2731 - 2737 (2015/09/15)
Herein, we demonstrated a benign and metal-free [3+2]-cycloaddition reaction using simple and readily available phenols and styrenes as substrates and sodium persulfate as an inexpensive and environmentally friendly oxidant for the direct synthesis of dih
Asymmetric synthesis of corsifuran A by an enantioselective oxazaborolidine reduction
Adams, Harry,Gilmore, Nathan J.,Jones, Simon,Muldowney, Mark P.,Von Reuss, Stephan H.,Vemula, Ramesh
supporting information; experimental part, p. 1457 - 1460 (2009/04/10)
(Chemical Equation Presented) Corsifuran A has been prepared in an enantiomerically pure form for the first time by an asymmetric reduction procedure, allowing confirmation of the absolute stereochemistry of the natural product as (R).
Intriguing formal [2+3] cycloaddition promoted by a hypervalent iodine reagent
Bérard, Didier,Giroux, Marc-André,Racicot, Léanne,Sabot, Cyrille,Canesi, Sylvain
, p. 7537 - 7544 (2008/12/20)
Treatment of various substituted phenols in the presence of iodobenzene diacetate, perfluorinated alcohols and furan, allylsilanes or cyclic enol ethers promotes an oxidative annulation process in moderate to useful yields. In only one step, this method p
Corsifurans A-C, 2-arylbenzofurans of presumed stilbenoid origin from Corsinia coriandrina (Hepaticae)
Von Reu?, Stephan H.,K?nig, Wilfried A.
, p. 3113 - 3118 (2007/10/03)
Chemical investigation of the diethyl ether extract from Corsinia coriandrina resulted in the identification and synthesis of three 4′,5-O-disubstituted 2-arylbenzofurans as new natural products together with (E)- and (Z)-3,4′-dimethoxystilbene. Chemical
