62495-31-2Relevant academic research and scientific papers
A Convenient Preparation of 3-Substituted Furans: Synthesis of Perillene and Dendrolasin
Barma,Kundu, Abhijit,Baati, Rachid,Mioskowski, Charles,Falck
, p. 1387 - 1389 (2002)
(Matrix Presented) R= alkyl, allyl, propargyl, aryl A variety of 3-substituted furans, including the natural products perillene and dendrolasin, are obtained in good yield via reductive annulation of 1,1,1-trichloroethyl propargyl ethers using catalytic Cr(II) regenerated by Mn/TMSCI.
Synthetic method of diarylmethanes
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Paragraph 0179; 0180; 0181; 0182; 0183, (2017/08/28)
The invention discloses a synthetic method of diarylmethanes. The method is characterized in that benzyl pseudohalide and aromatic boric acid are reacted in an organic solvent under alkaline condition. The method employs easily available raw materials, conversion is realized under effect of no transition metal catalysis, water-free and oxygen-free are not required, Lewis acid catalysis is not required, the method has wide substrate universality, and various substituted diarylmethanes can be synthesized by the method.
Coupling of arylboronic acids with benzyl halides or mesylates without adding transition metal catalysts
Wu, Guojiao,Xu, Shuai,Deng, Yifan,Wu, Chaoqiang,Zhao, Xia,Ji, Wenzhi,Zhang, Yan,Wang, Jianbo
, p. 8022 - 8030 (2016/11/19)
We report herein a transition-metal-free coupling reaction of arylboronic acids with benzyl halides and mesylates for the construction of C(sp2)[sbnd]C(sp3) bonds. A unique feature of this coupling reaction is the formation regioisomers in some cases. Mechanistic studies suggest that this reaction may proceed via an unprecedented Friedel–Crafts-type reaction pathway under base conditions with the assistance of boronic acid moiety.
Cobalt-Catalyzed Reductive Cross-Coupling Between Benzyl Chlorides and Aryl Halides
Pal, Suman,Chowdhury, Sushobhan,Rozwadowski, Elodie,Auffrant, Audrey,Gosmini, Corinne
, p. 2431 - 2435 (2016/08/16)
A new protocol for the direct reductive cobalt-catalyzed arylation of benzyl chlorides has been developed in order to form functionalized diarylmethanes. A variety of reactive groups either on the aryl or the benzyl halide was employed. This represents the first cobalt-catalyzed reductive cross-coupling which does not require any ligand and pyridine. A reaction pathway is proposed involving a radical benzyl species. (Figure presented.).
One-pot dual substitutions of bromobenzyl chloride, 2-chloromethyl-6- halogenoimidazo[1,2-a]pyridine and -[1,2-b]pyridazine by Suzuki-Miyaura cross-coupling reactions
Henry, Nicolas,Enguehard-Gueiffier, Cecile,Thery, Isabelle,Gueiffier, Alain
supporting information; experimental part, p. 4824 - 4827 (2009/05/07)
A very simple, mild and inexpensive palladium-catalyzed cross-coupling of (hetero)arylboronic acids with benzylic halides occurs in good yield. This method was successfully expanded to two heterocyclic electrophiles and allowed onepot dual substitutions of bromobenzyl chloride, 2-chloromethyl-6- halogenoimidazo[1,2-a]pyridine or -[1,2-b]pyridazine, leading to numerous new unsymmetrical methylenelinked biaryl systems. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.
Regioselective ortho lithiation of 3-aryl and 3-styryl furans
Tofi, Maria,Georgiou, Thomas,Montagnon, Tamsyn,Vassilikogiannakis, Georgios
, p. 3347 - 3350 (2007/10/03)
(Chemical Equation Presented) An unusual regioselectivity pattern for the ortho lithiation of 3-aryl and 3-styryl furans has been uncovered wherein lithiation occurs preferentially at the sterically encumbered 2-position. The results are attributed, at le
(Alkoxyallyl)sulfones as enal and enone β-anion equivalents. Synthesis of mono-, di- and trisubstituted furans
Craig, Donald,Etheridge, Christopher J.
, p. 15289 - 15310 (2007/10/03)
Treatment of variously-substituted (alkoxyallyl)sulfones 1, 7-9 with strong base followed by aldehydes gives alcohol adducts 5. These may be converted into a wide range of substituted furans 6 by exposure to acid, or to silica gel in dichloromethane containing sulfuric acid in some cases.
Benzylation via Tandem Grignard Reaction - Iodotrimethylsilane (TMSI) Mediated Reduction
Stoner, Eric J.,Cothron, Darlene A.,Balmer, Mary K.,Roden, Brian A.
, p. 11043 - 11062 (2007/10/02)
A method has been developed which allows for the large scale preparation of biarylmethanes.This method involves the initial formation of biarylmethanols via reaction of aryl Grignards with carbonyl compounds followed by a subsequent reduction with iodotrimethylsilane (TMSI).A number of improvements over existing literature procedures are reported as well as previously unobserved dimerizations.Studies reveal that as few as 3 equiv of TMSI will give complete reduction in most cases where either of the substituents are not heteroaromatic.Mono-substituted alkanols react with TMSI to afford the corresponding iodides.A mechanistic study of the TMSI reduction is also reported.
Synthesis of some 2,5-substituted 7-oxabicyclo[2.2.1]heptanes: Stereochemistry of Diels-Alder adducts of a 3-alkylfuran
Jarvest,Readshaw
, p. 962 - 965 (2007/10/02)
From the Diels-Alder reaction of 3-benzylfuran with acrylonitrile were isolated three of the four possible isomeric adducts, 5(or 6)-benzyl-7-oxabicyclo[2.2.1]hept-5-ene-2-endo(or exo)-carbonitriles 6-8, with the 5-benzyl-2-endo-carbonitrile 7 predominati
