16435-49-7Relevant academic research and scientific papers
Dilithium Amides as a Modular Bis-Anionic Ligand Platform for Iron-Catalyzed Cross-Coupling
Neate, Peter G.N.,Zhang, Bufan,Conforti, Jessica,Brennessel, William W.,Neidig, Michael L.
supporting information, p. 5958 - 5963 (2021/08/18)
Dilithium amides have been developed as a bespoke and general ligand for iron-catalyzed Kumada-Tamao-Corriu cross-coupling reactions, their design taking inspiration from previous mechanistic and structural studies. They allow for the cross-coupling of alkyl Grignard reagents with sp2-hybridized electrophiles as well as aryl Grignard reagents with sp3-hybridized electrophiles. This represents a rare example of a single iron-catalyzed system effective across diverse coupling reactions without significant modification of the catalytic protocol, as well as remaining operationally simple.
Iron-catalysed allylation-hydrogenation sequences as masked alkyl-alkyl cross-couplings
Bernauer, Josef,Wu, Guojiao,Von Wangelin, Axel
, p. 31217 - 31223 (2019/10/19)
An iron-catalysed allylation of organomagnesium reagents (alkyl, aryl) with simple allyl acetates proceeds under mild conditions (Fe(OAc)2 or Fe(acac)2, Et2O, r.t.) to furnish various alkene and styrene derivatives. Mechanistic studies indicate the operation of a homotopic catalyst. The sequential combination of such iron-catalysed allylation with an iron-catalysed hydrogenation results in overall C(sp3)-C(sp3)-bond formation that constitutes an attractive alternative to challenging direct cross-coupling protocols with alkyl halides.
Gram-Scale, Cheap, and Eco-Friendly Iron-Catalyzed Cross-Coupling between Alkyl Grignard Reagents and Alkenyl or Aryl Halides
Cahiez, Gérard,Lefèvre, Guillaume,Moyeux, Alban,Guerret, Olivier,Gayon, Eric,Guillonneau, Lo?c,Lefèvre, Nicolas,Gu, Qinzhuo,Zhou, Edouard
supporting information, p. 2679 - 2683 (2019/04/30)
A new robust methodology for gram-scale iron-catalyzed cross-coupling between alkyl Grignard reagents and alkenyl or aryl halides is developed. This method does not require toxic additives such as NMP or expensive ligands. Its efficiency relies on the use of simple alkoxide magnesium salts as additives. On the basis of these results, a new procedure for one-pot synthesis of substituted benzamides from chloroesters is also proposed.
Preparation of alkenes (by machine translation)
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Paragraph 0033, (2019/04/02)
[A] a method useful for industrial production of alkenes. General formula [a]1, 3 - Butadiene in the presence of a catalytic amount of a catalyst of iron or the like and represented in a vinyl carboxylate, R5 The Grignard reagent is reacted with MgX expressed by, general formulaPreparation of alkene represented. (R1 - R3 Is, independently of each other H, an alkyl group or an alkenyl group; R4 An alkyl group; R5 The alkyl group or alkenyl group; X is Cl, Br or I)[Drawing] no (by machine translation)
Isolation and structural characterization of geminal di(iodozincio)methane complexes stabilized with nitrogen ligands
Nishida, Yusuke,Hosokawa, Naoki,Murai, Masahito,Takai, Kazuhiko
, p. 114 - 117 (2015/01/30)
Treatment of gem-di(iodozincio)methane with pyridine or diamine derivatives resulted in the isolation of a storable gem-di(iodozincio)methane species. Use of the sterically bulky bipyridine ligand gave a gem-di(iodozincio)methane complex, which allowed the first X-ray structural analysis of such species. This work represents a rare example of the isolation of an organometallic reactive species in Schlenk equilibrium and thus provides new insight into the design of efficient and storable organometallic reagents. The isolated gem-di(iodozincio)methane complexes serve as effective methylene dianion synthons for olefination of carbonyl compounds.
Wittig type methylenation of ketones with bis(iodozincio)methane and ionic liquid
Yoshino, Hideaki,Kobata, Masami,Yamamoto, Yuhei,Oshima, Koichiro,Matsubara, Seijiro
, p. 1224 - 1224 (2007/10/03)
Ketones were transformed into alkenes via methylenation with bis(iodozincio)methane and ionic liquid, 1-butyl-3-methyl-imidazolium hexafluorophosphate ([bmim][PF6]) in the absence of additional metal salt such as titanium chlorides.
Palladium-catalyzed negishi cross-coupling reactions of unactivated alkyl iodides, bromides, chlorides, and tosylates
Zhou, Jianrong,Fu, Gregory C.
, p. 12527 - 12530 (2007/10/03)
A single method (2% Pd2(dba)3/8% PCyp 3/NMI in THF/NMP at 80°C; Cyp = cyclopentyl) achieves the cross-coupling of a range of β-hydrogen-containing primary alkyl iodides, bromides, chlorides, and tosylates with an array of alkyl-, alkenyl-, and arylzinc halides. The process is compatible with a variety of functional groups, including esters, amides, imides, nitriles, and heterocycles.
Methylenation of carbonyl compounds by means of Nysted reagent
Matsubara, Seijiro,Sugihara, Masakazu,Utimoto, Kiitiro
, p. 313 - 315 (2007/10/03)
Nysted reagent [cyclo-dibromodi-μ-methylene(μ-tetrahydrofuran)trizinc], a commercially available gem-dimetallic compound, reacted with aldehydes affording methylenated products in the presence of BF3?OEt2, whereas methylenation of ketones proceeded in the presence of BF3OEt2 and TiCl2.
Alkylidenation of carbonyl compounds with gem-dizincioalkanes mediated with titanium dichloride
Matsubara, Seijiro,Mizuno, Tsuyoshi,Otake, Tasuyuiki,Kobata, Masami,Utimoto, Kiitiro,Takai, Kazuhiko
, p. 1369 - 1371 (2007/10/03)
Olefination of carbonyl compounds with gem-dizincio-alkanes, bis(iodozincio)methane, 1,1-bis(iodozincio)ethane, and bis(bromozincio)methyltrimethylsilane, afforded the corresponding olefins in good to excellent yields.
ORGANIC SYNTHESIS WITH REAGENTS DERIVED FROM 3R3SiMgMe AND MnCl2
Fugami, Keigo,Hibino, Jun-ichi,Nakatsukasa, Shigeki,Matsubara, Seijiro,Oshima, Koichiro,et al.
, p. 4277 - 4292 (2007/10/02)
Synthetically useful reactions mediated by reagents derived from 3 equiv. of R3SiMgMe and MnCl2 are disclosed. (1) The manganese species reacted with terminal acetylenes to give 1,2-disilylated 1-alkenes.Mono- and bis(trimethylsilyl)acetylenes gave tri- a
