85656-22-0Relevant academic research and scientific papers
Indium(I) iodide-catalyzed regio- and diastereoselective formal α-addition of an α-methylallylboronate to N-acylhydrazones
Kobayashi, Shu,Konishi, Hideyuki,Schneider, Uwe
, p. 2313 - 2315 (2008)
Indium(I) iodide was found to catalyze the formal α-addition of an α-methylallylboronate to various N-acylhydrazones, in the presence of an alcohol additive, to afford the corresponding anti-α-adducts with high regio- and diastereoselectivity in high yiel
Indium-mediated allylation of carbonyl compounds in deep eutectic solvents
González-Gallardo, Nerea,Saavedra, Beatriz,Guillena, Gabriela,Ramón, Diego J.
, (2021/08/26)
This study describes, for the first time, the in situ generation of indium organometallic reagents in environmentally friendly deep eutectic solvents (DESs). The allylation process of different carbonyl compounds is achieved mediated by indium metal and u
Direct use of 1,3-dienes for the allylation of ketones: Via catalytic hydroindation
Miyamoto, Shinji,Shibata, Ikuya,Suzuki, Itaru,Yagi, Kensuke
, p. 6030 - 6034 (2020/02/26)
In this study, in situ catalytically generated allylic indium from 1,3 dienes and InCl2H was developed for use in the allylation of ketones. This protocol resulted in the unprecedented establishment of a successive combining of quaternary C-C b
[bmim][Br] as an Inexpensive and Efficient Medium for the Barbier-Type Allylation Reaction Using a Catalytic Amount of Indium: Mechanistic Studies
Dey, Papiya,Koli, Mrunesh,Goswami, Dibakar,Sharma, Anubha,Chattopadhyay, Subrata
, p. 1333 - 1341 (2018/04/02)
Barbier-type allylation reactions of aldehydes and ketones have been carried out with both unsubstituted and γ-substituted allyl bromides using only a catalytic amount (0.1 equiv.) of In metal in [bmim][Br], but not in H2O, organic solvents, or
Catalytic use of zinc amide for transmetalation with allylboronates: General and efficient catalytic allylation of carbonyl compounds, imines, and hydrazones
Cui, Yi,Li, Wei,Sato, Takehiro,Yamashita, Yasuhiro,Kobayashi, Shu
, p. 1193 - 1205 (2013/06/04)
The efficient catalytic allylation of ketones, imines, and hydrazones with allylboronates using a catalytic amount of zinc amide is reported. In this reaction, the boron-to-zinc exchange process occurred smoothly to afford the corresponding allylzinc amides, and the desired allylation reactions proceeded in high efficiency (~0.1mol%). A mechanistic study revealed that transmetalation was a rate-determining step in the catalytic cycle, and also that the amide ligand on the zinc center played a key role in preparing reactive allylzinc species. Catalytic asymmetric allylations were also investigated, and high enantioselectivities were obtained using chiral diamine ligands. Copyright
Facile preparation of allylzinc species from allylboronates and zinc amide via a boron-to-zinc exchange process and their reactions with carbonyl compounds, imines and hydrazones
Cui, Yi,Yamashita, Yasuhiro,Kobayashi, Shu
supporting information, p. 10319 - 10321 (2012/11/07)
Facile formation of allylzinc species from allylboronate and zinc amide was discovered. The boron-to-zinc exchange process occurred smoothly to afford the corresponding allylzinc amides, which were successfully employed in catalytic allylation reactions with electrophiles. Asymmetric catalysis using a chiral zinc amide is also reported.
Titanocene(III)-promoted Barbier-type crotylation of carbonyl compounds
Sancho-Sanz, Iris,Miguel, Delia,Millan, Alba,Estevez, Rosa E.,Oller-Lopez, Juan L.,Alvarez-Manzaneda, Enrique,Robles, Rafael,Cuerva, Juan M.,Justicia, Jose
experimental part, p. 732 - 735 (2011/03/20)
A mild, highly regio-and stereoselective method for the crotylation of aldehydes and ketones mediated/catalyzed by titanocene(III) is described. Optimized conditions permit the selective generation of γ-adducts in high yields together with high stereoselectivity, with a predominance of anti stereoisomers.
Regio- and stereoselective preparation of highly substituted tertiary homoallylic alcohols
Takeda, Takeshi,Wasa, Hideki,Tsubouchi, Akira
scheme or table, p. 4575 - 4578 (2011/09/20)
The titanocene(II)-promoted reaction of α-(benzyldimethylsilyl) allylic sulfides with ketones proceeded with high regio- and stereoselectivity to give δ-silylhomoallylic alcohols. The following palladium catalyzed cross-couplings with organic halides prod
Catalytic use of a soluble organoindium(III) species for allylation and crotylation of ketones with boronates
Yamaguchi, Miyuki,Morita, Naohide,Schneider, Uwe,Kobayashi, Shu
supporting information; experimental part, p. 1461 - 1465 (2010/08/20)
The unprecedented use of a soluble organoindium species, indium(III) hexamethyldisilazide [In(III)(hmds)3], for catalytic carbon-carbon bond formations between ketones and boronates, is reported. Various functionalized tertiary homoallyl alcoho
Mild and general zinc-alkoxide-catalyzed allylations of ketones with allyl pinacol boronates
Fandrick, Keith R.,Fandrick, Daniel R.,Gao, Joe J.,Reeves, Jonathan T.,Tan, Zhulin,Li, Wenjie,Song, Jinhua J.,Lu, Bruce,Yee, Nathan K.,Senanayake, Chris H.
supporting information; experimental part, p. 3748 - 3751 (2010/11/18)
A general and efficient zinc-alkoxide-catalyzed allylation of a diverse array of ketones with allyl boronates is presented. The methodology is effective with 2 mol % of catalyst and with relatively short reaction times. Studies of the key exchange process are presented, which support a cyclic transition state for the boron to zinc exchange.
