110577-96-3Relevant academic research and scientific papers
SnCl2·2H2O-mediated Barbier-type allylation: A comparative evaluation of the catalytic performance of CuI and Pd(OAc) 2
Kalita, Pabitra Kumar,Phukan, Prodeep
, p. 1055 - 1062 (2013)
A systematic investigation has been carried out for the allylation of carbonyl compounds under SnCl2·2H2O-mediated Barbier-type conditions, using CuI and Pd(OAc)2 as catalysts. Ketones, which are not reactive under the influence of CuI, however, could be activated by using Pd(OAc)2 as a catalyst.
Gadolinium(III) chloride: a novel and an efficient reagent for the synthesis of homoallylic alcohols
Lingaiah, B. Venkat,Ezikiel,Yakaiah,Reddy, G. Venkat,Rao, P. Shanthan
, p. 4315 - 4318 (2006)
Carbonyl compounds efficiently undergo nucleophilic addition reactions with allylstannanes in the presence of GdCl3·6H2O in acetonitrile under extremely mild reaction conditions to give the corresponding homoallylic alcohols in excellent yields and with high chemoselectivity.
Noticeable facilitation of the bismuth-mediated Barbier-type allylation of aromatic carbonyl compounds under solvent-free conditions
Wada, Shinobu,Hayashi, Nobuyuki,Suzuki, Hitomi
, p. 2160 - 2163 (2003)
When milled together with bismuth shot in the presence of allyl halide, aromatic aldehydes readily underwent a Barbier-type allylation to afford the corresponding homoallyl alcohols in good yield. In contrast to the failure in solution reaction, aromatic
Self-assembled organic nanotube promoted allylation of ketones in aqueous phase
Sun, Hui,Jiang, Jian,Sun, Yimeng,Zhang, Qingwu,Liu, Minghua
, p. 3254 - 3257 (2019)
A self-assembled organic nanotube was found to promote the allylation of ketones in the aqueous phase.
Transition-metal-catalyzed Grignard Reaction of Isoprene Bromohydrin
Araki, Shuki,Ohmura, Masayuki,Butsugan, Yasuo
, p. 1607 - 1608 (1985)
The coupling reaction of isoprene bromohydrin with aryl and alkyl Grignard reagents catalyzed by tetrakis(triphenylphosphine)palladium(0) selectively gave the vinyl-group-migrated products.
Indium triflate catalyzed allylation of ketones with diallyldibutyltin
Liu, Ling-Yan,Tang, Long,Yu, Lei,Chang, Wei-Xing,Li, Jing
, p. 10930 - 10934 (2005)
A series of ketones underwent an allylation reaction using diallyldibutyltin in the presence of a catalytic amount of In(OTf)3. The method was found to be superior to most of the known methods. Thus, a new allyltin reagent Bu2Sn(allyl)2/In(OTf)3 for ketones was developed.
Allylation of ketones with allylstannanes catalyzed by Lewis acid-Lewis base combined reagents
Hamasaki,Chounan,Horino,Yamamoto
, p. 9883 - 9887 (2000)
Although the Lewis acid promoted allylation of ketones with allylstannanes gives the corresponding tert-homoallyl alcohols in lower yields in comparison with those of aldehydes, the use of Lewis acid-Lewis base combined catalysts such as Zn(OTf)2-2,6-lutidine and Zn(OTf)2-pyridine dramatically enhances the yield of the tert-alcohols. (C) 2000 Published by Elsevier Science Ltd.
A Mechanochemical Zinc-Mediated Barbier-Type Allylation Reaction under Ball-Milling Conditions
Yin, JieXiang,Stark, Roderick T.,Fallis, Ian A.,Browne, Duncan L.
, p. 2347 - 2354 (2020/02/04)
A ball-milling-enabled zinc-mediated Barbier-type allylation reaction is reported. Notably, running the reaction in this manner renders it effective irrespective of the initial morphology of the zinc metal. The process is operationally simple, does not re
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.
Use of allylzinc halide as a source of halide: Differential addition of nucleophiles to Ts-aziridines and aldehydes under similar reaction conditions
Chatterjee, Rana,Samanta, Satyajit,Mukherjee, Anindita,Santra, Sougata,Zyryanov, Grigory V.,Majee, Adinath
supporting information, p. 276 - 283 (2019/01/04)
We have observed that the allylic zinc halide under identical reaction conditions acts in different modes for different electrophiles. For Ts-aziridines the halide part of the allylic halide has been introduced as a nucleophile and for the carbonyl compou
