37542-92-0Relevant academic research and scientific papers
Nickel-catalyzed cross-coupling of aldehydes with aryl halides: Via hydrazone intermediates
Tang, Jianting,Lv, Leiyang,Dai, Xi-Jie,Li, Chen-Chen,Li, Lu,Li, Chao-Jun
, p. 1750 - 1753 (2018/02/21)
Traditional cross-couplings require stoichiometric organometallic reagents. A novel nickel-catalyzed cross-coupling reaction between aldehydes and aryl halides via hydrazone intermediates has been developed, merging the Wolff-Kishner reduction and the classical cross-coupling reactions. Aromatic aldehydes, aryl iodides and aryl bromides are especially effective in this new cross-coupling chemistry.
Substrate switchable Suzuki-Miyaura coupling for benzyl ester: Vs. benzyl halide
Ohsumi, Masato,Ito, Akitaka,Nishiwaki, Nagatoshi
, p. 35056 - 35061 (2018/10/24)
Two reaction conditions were developed to accomplish the substrate switchable Suzuki-Miyaura coupling of benzyl derivatives and arylboronic acid derivatives. Under conditions for esters, benzyl esters such as carbonates and acetates reacted with arylboronic acids to afford the corresponding diarylmethanes. However, the benzyl halides did not react under the same conditions. On the other hand, benzyl halides such as bromides and chlorides furnished diarylmethanes under conditions for halides, under which benzyl ester substrates did not react, in which water was found to play an important role. This switching system was tested using the intermolecular/intramolecular competitive reactions, during which the desired products could be synthesized by selecting the appropriate reaction conditions.
Cross-Coupling of Phenol Derivatives with Umpolung Aldehydes Catalyzed by Nickel
Lv, Leiyang,Zhu, Dianhu,Tang, Jianting,Qiu, Zihang,Li, Chen-Chen,Gao, Jian,Li, Chao-Jun
, p. 4622 - 4627 (2018/05/22)
A nickel-catalyzed cross-coupling to construct the C(sp2)-C(sp3) bond was developed from two sustainable biomass-based feedstocks: phenol derivatives with umpolung aldehydes. This strategy features the in situ generation of moisture/air-stable hydrazones from naturally abundant aldehydes, which act as alkyl nucleophiles under catalysis to couple with readily available phenol derivatives. The avoidance of using both halides as the electrophiles and organometallic or organoboron reagents (also derived from halides) as the nucleophiles makes this method more sustainable. Water tolerance, great functional group (ketone, ester, free amine, amide, etc.) compatibility, and late-stage elaboration of complex biological molecules exemplified its practicability and unique chemoselectivity over organometallic reagents.
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.).
Sodium borohydride-nickel chloride-methanol catalytic system for regioselective reduction of electron-rich conjugated dienes and reductive cleavage of allyl esters involving π-allylnickel intermediates
Yin, Biao-Lin,Cai, Cong-Bi,Lai, Jin-Qiang,Zhang, Ze-Ren,Huang, Li,Xu, Li-Wen,Jiang, Huan-Feng
supporting information; experimental part, p. 3319 - 3324 (2012/01/30)
The regioslective reduction of electron-rich dienes to monoolefins and the reductive cleavage of allyl esters were fulfilled by employing a sodium borohydride-nickel chloride-methanol catalytic system with exceedingly simple manipulations and high functional group tolerability. Both of the reductive reactions may involve π-allylnickel intermediates generated from fresh nickel boride. Copyright
Synthesis of 2-substituted furans by iron- and palladium-catalyzed coupling reactions
Haner, Jamie,Jack, Kelsey,Nagireddy, Jaipal,Raheem, Mohammed Abdul,Durham, Robin,Tam, William
experimental part, p. 731 - 738 (2011/04/24)
The synthesis of 2-substituted furans via palladium- and iron-catalyzed coupling utilizing 2-bromofuran is described. Whereas palladium-catalyzed Suzuki coupling effectively provided the corresponding aryl furans, little or no product was obtained by palladium-catalyzed coupling with various alkyl nucleophiles. Iron-catalyzed coupling proved effective for the synthesis of primary and secondary alkyl furans in modest yields and aryl furans in low yields. Georg Thieme Verlag Stuttgart New York.
Gold-catalyzed substitution reaction with ortho-alkynylbenzoic acid alkyl ester as an efficient alkylating agent
Aikawa, Haruo,Tago, Sakie,Umetsu, Kazuteru,Haginiwa, Naomichi,Asao, Naoki
experimental part, p. 1774 - 1784 (2009/06/20)
ortho-Alkynylbenzoic acid alkyl esters behave as alkylating agents in combination with gold catalysts. The reaction with alcohols occurs smoothly in the presence of catalytic amounts of Ph3PAuCl and AgOTf under mild conditions to produce the corresponding ether products in high yields. The protocol is also useful for Friedel-Crafts alkylation and N-alkylation of sulfonamides. The reaction likely proceeds through the gold-induced in situ construction of leaving groups and subsequent nucleophilic attack of nucleophiles, such as alcohols, aromatic compounds, and sulfonamides.
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.
