60573-61-7Relevant articles and documents
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
Heterocyclization involving benzylic C(sp3)-H functionalization enabled by visible light photoredox catalysis
Pandey, Ganesh,Laha, Ramkrishna,Mondal, Pradip Kumar
supporting information, p. 9689 - 9692 (2019/08/15)
A general and efficient method for heterocyclization involving benzylic C(sp3)-H functionalization enabled by visible light photoredox catalysis to access a wide range of structurally diverse oxygen as well as nitrogen heterocycles up to a gram scale is reported. The potential application of this new methodology is demonstrated by the total synthesis of (-)-codonopsinine and (+)-centrolobine. Herein it is proposed that selectfluor, unlike a fluorinating reagent, acts as an oxidative quencher and a hydrogen radical acceptor.
Self-assembled organic nanotube promoted allylation of ketones in aqueous phase
Sun, Hui,Jiang, Jian,Sun, Yimeng,Zhang, Qingwu,Liu, Minghua
supporting information, p. 3254 - 3257 (2019/04/06)
A self-assembled organic nanotube was found to promote the allylation of ketones in the aqueous phase.
A Green approach for allylations of aldehydes and ketones: Combining allylborate, mechanochemistry and lanthanide catalyst
De Souza, Viviane P.,Oliveira, Cristiane K.,De Souza, Thiago M.,Menezes, Paulo H.,Alves, Severino,Longo, Ricardo L.,Malvestiti, Ivani
, (2016/12/02)
Secondary and tertiary alcohols synthesized via allylation of aldehydes and ketones are important compounds in bioactive natural products and industry, including pharmaceuticals. Development of a mechanochemical method using potassium allyltrifluoroborate salt and water, to successfully perform the allylation of aromatic and aliphatic carbonyl compounds is reported for the first time. By controlling the grinding parameters, the methodology can be selective, namely, very efficient for aldehydes and ineffective for ketones, but by employing lanthanide catalysts, the reactions with ketones can become practically quantitative. The catalyzed reactions can also be performed under mild aqueous stirring conditions. Considering the allylation agent and its by-products, aqueous media, energy efficiency and use of catalyst, the methodology meets most of the green chemistry principles.
Nickel-catalyzed reductive allylation of ketones with allylic carbonates
Zhao, Chenglong,Tan, Zhuozhen,Liang, Zhuye,Deng, Wei,Gong, Hegui
supporting information, p. 1901 - 1907 (2014/07/22)
Nickel-catalyzed efficient umpolung allylation of ketones with allylic carbonates in the presence of zinc powder is developed, which accommodates a variety of allylic and ketone substrates. Although chiral ligand is necessary for the transformation, no enantioselectivity was observed. Georg Thieme Verlag Stuttgart New York.
Asymmetric allylation of ketones and subsequent tandem reactions catalyzed by a novel polymer-supported titanium-binolate complex
Yadav, Jagjit,Stanton, Gretchen R.,Fan, Xinyuan,Robinson, Jerome R.,Schelter, Eric J.,Walsh, Patrick J.,Pericas, Miquel A.
supporting information, p. 7122 - 7127 (2014/06/09)
By using a novel, simple, and convenient synthetic route, enantiopure 6-ethynyl-BINOL (BINOL=1,1-binaphthol) was synthesized and anchored to an azidomethylpolystyrene resin through a copper-catalyzed alkyne-azide cycloaddition (CuAAC) reaction. The polyst
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
supporting information, 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
Rhodium-catalyzed redox allylation reactions of ketones
Williams, Florence J.,Grote, Robin E.,Jarvo, Elizabeth R.
supporting information; experimental part, p. 1496 - 1498 (2012/03/26)
Ketones react with allyl acetate to generate tertiary homoallylic alcohols in the presence of a rhodium catalyst and bis(pinacolato)diboron. A range of substrates, including aryl, alkyl and cyclic ketones react smoothly under these conditions. Diastereoselective allylation reactions of functionalized ketones such as pregnenolone acetate are also reported.
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.
Catalytic use of a soluble organoindium(III) species for allylation and crotylation of ketones with boronates
Yamaguchi, Miyuki,Morita, Naohide,Schneider, Uwe,Kobayashi, Shu
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
