110577-96-3Relevant articles and documents
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.
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
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.
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.
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.
Hydroxyl group-assisted palladium-catalyzed lactonization of homoallylic alcohols
Huang, Liangbin,Wang, Qian,Wu, Wanqing,Jiang, Huanfeng
, p. 561 - 566 (2014/03/21)
A convenient and highly efficient synthesis of α-methylene-γ- lactones through the palladium(II)-catalyzed lactonization of homoallylic alcohols with alkynamides has been reported. The hydroxyl group in the terminal olefins cooperates with the amide in alkynamides to promote the cyclization by suppressing the β-H elimination. This process provides a route to construct naturally occurring biologically multifunctional α-methylene-γ- lactones. The time has come to.i?lactonize: α-Methylene- γ-lactones are synthesized through the PdII-catalyzed lactonization of homoallylic alcohols with alkynamides. The hydroxyl group in the terminal olefins cooperates with the amide in alkynamides to promote the cyclization by suppressing the β-H elimination. This provides a route towards naturally occurring biologically multifunctional α-methylene- γ-lactones. Copyright
