4165-79-1Relevant 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
Organocatalytic Trapping of Elusive Carbon Dioxide Based Heterocycles by a Kinetically Controlled Cascade Process
Bo, Carles,Kleij, Arjan W.,Limburg, Bart,Qiao, Chang,Sprachmann, Josefine,Villar-Yanez, Alba
supporting information, p. 18446 - 18451 (2020/08/21)
A conceptually novel approach is described for the synthesis of six-membered cyclic carbonates derived from carbon dioxide. The approach utilizes homoallylic precursors that are converted into five-membered cyclic carbonates having a β-positioned alcohol group in one of the ring substituents. The activation of the pendent alcohol group through an N-heterocyclic base allows equilibration towards a thermodynamically disfavored six-membered carbonate analogue that can be trapped by an acylating agent. Various control experiments and computational analysis of this manifold are in line with a process that is primarily dictated by a kinetically controlled acylation step. This cascade process delivers an ample diversity of six-membered cyclic carbonates in excellent yields and chemoselectivities under mild reaction conditions.
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.
[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
Photocatalytic Barbier reaction-visible-light induced allylation and benzylation of aldehydes and ketones
Berger, Anna Lucia,Donabauer, Karsten,K?nig, Burkhard
, p. 7230 - 7235 (2018/10/02)
We report a photocatalytic version of the Barbier type reaction using readily available allyl or benzyl bromides and aromatic aldehydes or ketones as starting materials to generate allylic or benzylic alcohols. The reaction proceeds at room temperature under visible light irradiation with the organic dye 3,7-di(4-biphenyl)1-naphthalene-10-phenoxazine as a photocatalyst and DIPEA as sacrificial electron donor. The proposed cross-coupling mechanism of a ketyl- and an allyl or benzyl radical is supported by spectroscopic investigations and cyclic voltammetry measurements.
Preparation method and application of 2-hydroxymethyloxetane derivative
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Paragraph 0130-0133, (2018/12/14)
The invention discloses a preparation method and application of a 2-hydroxymethyloxetane derivative. The method comprises the following steps that a compound II and a compound III are used as raw materials; Barbier reaction is performed to obtain a compound IV; olefinic bonds in the compound IV are cyclized and oxidized to obtain a compound V; under the alkaline condition, ring opening is performed to generate a compound VI; after ring closing reaction, a compound VII is obtained; finally, benzyl protecting groups are removed to obtain the 2-hydroxymethyloxetane derivative (the compound I).
Electrochemically Enabled Carbohydroxylation of Alkenes with H2O and Organotrifluoroborates
Xiong, Peng,Long, Hao,Song, Jinshuai,Wang, Yaohui,Li, Jian-Feng,Xu, Hai-Chao
supporting information, p. 16387 - 16391 (2018/11/23)
Unprecedented hydroxy-alkynylation and -alkenylation reactions of arylalkenes have been developed through electrochemically enabled addition of an organotrifluoroborate reagent and H2O across the double bond of the alkene. The use of electrochemistry to promote these oxidative alkene 1,2-difunctionalization reactions not only obviates the need for transition-metal catalysts and oxidizing reagents but also ensures high regio- and chemoselectivity to afford homopropargylic or homoallylic alcohols. The possibility of extending the electrochemical alkene difunctionalization strategy to other alkene carbo-heterofunctionalization reactions has been demonstrated.
Synthesis and antifungal activity of new dihydrofurocoumarins and dihydrofuroquinolines
Ustalar, Asli,Yilmaz, Mehmet,Osmani, Agim,Ke?eli, Sema A?kin
, p. 80 - 88 (2017/03/14)
We investigated the radical addition of 4-hydroxycoumarin (1a) and 4-hydroxyquinoline (1b) with conjugated dienes (2a-f) mediated by cerium(IV) ammonium nitrate (CAN) resulting in ethenyl substituted 2,3-dihydrofurocoumarin (3a-f) and 3,5-dihydrofuroquino
MeOH or H2O as efficient additive to switch the reactivity of allylSmBr towards carbonyl compounds
Li, Jianyong,Niu, Qingsheng,Li, Shanchan,Sun, Yuehao,Zhou, Qian,Lv, Xin,Wang, Xiaoxia
supporting information, p. 1250 - 1253 (2017/03/10)
A variety of carbonyl compounds were treated by allylSmBr (allylSmBr) with MeOH as the cosolvent to have further insights on the previously reported reductive coupling of aryl ketones mediated by Sm/alkyl halide/MeOH. The results demonstrate that the real reducing species in Sm/alkyl halide/MeOH system should be allylSmBr, and MeOH has elegantly switched the reactivity of allylSmBr from being nucleophilic to being good reductive coupling reagent. Besides, H2O was also found to be a useful additive to realize the pinacol coupling of aliphatic aldehydes and ketones promoted by allylSmBr.
Nucleo-Palladation-Triggering Alkene Functionalization: A Route to γ-Lactones
Zheng, Meifang,Chen, Pengquan,Huang, Liangbin,Wu, Wanqing,Jiang, Huanfeng
supporting information, p. 5756 - 5759 (2017/11/10)
An unprecedented strategy for the highly effective synthesis of γ-lactones from homoallylic alcohols was achieved by palladium catalysis in one step. The protocol affords aryl, alkyl, and spiro γ-lactones directly from readily available homoallylic alcohols in good yields with excellent functional group tolerance and high chemoselectivity under mild conditions.
