113386-21-3Relevant academic research and scientific papers
Efficient Pd-catalyzed heterobenzylic cross-coupling using sulfonium salts as substrates and (PhO)3P as a supporting ligand
Zhang, Shijie,Marshall, Daniel,Liebeskind, Lanny S.
, p. 2796 - 2804 (1999)
S-(2-Furanylmethyl)tetramethylenesulfonium hexafluorophosphate, S-(2-thienylmethyl)tetramethylenesulfonium hexafluorophosphate, S-(3-thienylmethyl)tetramethylenesulfonium hexafluorophosphate, and S-(N-tert-butoxycarbonyl-2-pyrrolylmethyl)tetramethylenesulfonium hexafluorophosphate have been conveniently prepared from the corresponding alcohols. These stable heterobenzylic sulfonium salts participate in palladium-catalyzed Stille cross-couplings with organostannanes. All but the last mentioned sulfonium salt are also active participants in palladium-catalyzed cross-coupling reactions with boronic acids and organozinc halides. Because the heterobenzylic cross-coupling reactants are potent alkylating agents, they scavenge the typical phosphines and arsines that otherwise could be used to stabilize the palladium catalyst over extended reaction times. This problem was overcome by the use of (PhO)3P as a unique supporting ligand for the palladium-catalyzed cross-coupling of heterobenzylic sulfonium salts.
BASE CLEAVAGE OF SUBSTITUTED - AND -TRIMETHYLSILANE. STABILIZATION OF CARBANIONIC CENTRES BY 2-THIENYL AND 2-FURYL GROUPS
Eaborn, Colin,Pirazzini, Graziella,Seconi, Giancarlo,Ricci, Alfredo
, p. 339 - 346 (1980)
Rates of cleavage by NaOMe-MeOH at 25 deg C have been determined for (2-thienyl)2CHSiMe3 and for the compounds Ph(2-thienyl)CHSiMe3 and Ph(2-furyl)CHSiMe3 and some of their derivatives with a substituent in the m- or p-position of the phenyl group or the
AsCat and FurCat: New Pd catalysts for selective roomerature Stille cross-couplings of benzyl chlorides with organostannanes
Ronson, Thomas O.,Carney, Jonathan R.,Whitwood, Adrian C.,Taylor, Richard J. K.,Fairlamb, Ian J. S.
, p. 3466 - 3469 (2015)
Two novel succinimide-based palladium complexes, AsCat and FurCat, are highly efficient catalysts for roomerature Stille cross-coupling of organostannanes with benzyl chlorides. The air- and moisture-stable catalysts are prepared in one step, and the coupling reactions proceed with a high selectivity for the benzyl position under mild conditions without the need for additives. This journal is
Selective Conversion of Benzylic Phosphates into Diarylmethanes Through Al(OTf)3-Catalyzed Friedel–Crafts-Type Benzylation
Yurino, Taiga,Hachiya, Asuka,Suzuki, Keisuke,Ohkuma, Takeshi
, p. 2225 - 2232 (2020/04/16)
Al(OTf)3 was identified as a high-performance catalyst for Friedel–Crafts-type benzylation using benzylic phosphates as electrophiles. The reaction proceeded even with 0.2 mol-% of the catalyst. A series of diarylmethanes (21 examples) was obtained in moderate to high yield. The catalyst showed unique chemoselectivity, preferentially converting the benzylic phosphate motif, even with a benzylic acetate group existed in the same molecule.
Synthetic method of diarylmethanes
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Paragraph 0092; 0093; 0094; 0095; 0096, (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.
Intra- and Intermolecular Nickel-Catalyzed Reductive Cross-Electrophile Coupling Reactions of Benzylic Esters with Aryl Halides
Konev, Mikhail O.,Hanna, Luke E.,Jarvo, Elizabeth R.
, p. 6730 - 6733 (2016/06/09)
Nickel-catalyzed cross-electrophile coupling reactions of benzylic esters and aryl halides have been developed. Both inter- and intramolecular variants proceed under mild reaction conditions. A range of heterocycles and functional groups are tolerated under the reaction conditions. Additionally, the first example of a stereospecific cross-electrophile coupling of a secondary benzylic ester is described. Crossed off: Nickel-catalyzed cross-electrophile coupling reactions of benzylic esters and aryl halides have been developed. Both inter- and intramolecular variants proceed under mild reaction conditions, and a range of heterocycles and functional groups are tolerated. Additionally, the first example of a stereospecific cross-electrophile coupling of a secondary benzylic ester is described.
Amino derivatives of phenyl alkyl thiophene as inhibitors of bone resorption. Structure-activity relationship
Wierzbicki, Michel,Boussard, Marie-Francoise,Sauveur, Frederic,Kirsch, Gilbert,Sabatini, Massimo,Lesur, Christophe,Trodjman, Charles,Bonnet, Jacqueline
, p. 840 - 849 (2007/10/03)
Metabolism of arachidonic acid through the 5-lipoxygenase (LO) pathway generates compounds that stimulate osteoclastic bone resorption; since LO metabolites might play a role in bone loss due to excessive resorption it was tried to develop a series of antiresorptive agents starting from an already known LO inhibitor. Of the 35 compounds synthesized, 11 strongly inhibited (10 μmol/l) retinoic acid-induced bone resorption in cultured mouse calvariae; they were also tested for their effect on LO activity using rat peritoneal neutrophils, but no correlation could be drawn between inhibition of LO and bone resorption. Other pathways, still to be identified, must therefore be targeted by these compounds even though LO inhibition might contribute to their effects on bone. Two compounds selected for further studies were found active on parathyroid hormone-induced osteolysis, while they had no effect on basal resorption; they must, therefore, act at some key point in the process of activation of osteoclastic resorption. This series of compounds may represent a new way for the treatment of bone loss due to excessive resorption.
A general, convenient and highly efficient synthesis of diarylmethanes by copper-catalyzed reaction
Ku, Yi-Yin,Patel, Ramesh R.,Sawick, David P.
, p. 1949 - 1952 (2007/10/03)
Copper-catalyzed reactions of arylmagnesium derivatives with benzyliodides have been developed for the large scale preparation of diarylmethanes. Various diarylmethanes have been prepared in high yield by this reaction, the amount of homocoupled dimers be
