30134-52-2Relevant academic research and scientific papers
Palladium-catalyzed double-bond migration of unsaturated hydrocarbons accelerated by tantalum chloride
Murai, Masahito,Nishimura, Kengo,Takai, Kazuhiko
, p. 2769 - 2772 (2019/03/23)
The operationally simple palladium-catalyzed double-bond migration without heteroatom-containing coordinating functional groups is described. Addition of TaCl5 as a second catalyst greatly enhanced the migration efficiency to provide β-alkylsty
Base-catalysed reductive relay hydroboration of allylic alcohols with pinacolborane to form alkylboronic esters
Wang, Zi-Chao,Shen, Di,Gao, Jian,Jia, Xian,Xu, Youjun,Shi, Shi-Liang
, p. 8848 - 8851 (2019/08/01)
An unprecedented base-catalysed reductive relay hydroboration of allylic alcohols is described. Commercially available nBuLi was found to be a robust transition metal-free initiator for this protocol, affording various boronic esters in high yield and selectivity. Mechanistically, this methodology involves a one-pot three-step successive process (dehydrocoupling/allylic hydride substitution/anti-Markovnikov hydroboration).
Chemo- and regioselective reductive transposition of allylic alcohol derivatives via iridium or rhodium catalysis
Lundgren, Rylan J.,Thomas, Bryce N.
, p. 958 - 961 (2016/01/20)
We report highly chemo- and regioselective reductive transpositions of methyl carbonates to furnish olefin products with complementary regioselectivity to that of established Pd-catalysis. These Rh- and Ir-catalysed transformations proceed under mild conditions and enable selective deoxygenation in the presence of functional groups that are susceptible to reduction by metal hydrides.
A straightforward organocatalytic alkylation of 2-arylacetaldehydes: An approach towards bisabolanes
Gualandi, Andrea,Canestrari, Pietro,Emer, Enrico,Cozzi, Pier Giorgio
supporting information, p. 528 - 536 (2014/05/20)
A highly stereoselective organocatalytic aalkylation of 2-arylacetaldehydes with a commercially available carbenium tetrafluoroborate is described. The stereoselective alkylation was carried out in acetonitrile/ water, under air in the presence of a commercially available imidazolidinone (MacMillan's catalyst). Key intermediates for the synthesis of bisabolanes were obtained through a simple chemistry. In particular a direct, enantioselective and facile synthesis of (R)-(-)-curcumene is described.
Substituent Effects on the Intramolecular Photochemical Reactions of Phenyl-Ethenyl Non-conjugated Bichromophoric Systems
Ellis-Davies, Graham C. R.,Gilbert, Andrew,Heath, Peter,Lane, Jon C.,Warrington, John V.,Westover, David L.
, p. 1833 - 1842 (2007/10/02)
The effects of substitution on the photochemistry of phenyl-ethenyl bichromophoric systems are reported.Methyl substitution at the 2-, 3-, 5-, and 1,1,2-positions in the pentene moiety of 5-phenylpent-1-ene reduces both reaction efficiency and selectivity but in contrast to intramolecular analogues the photoreaction of 3-phenethylcyclohexene is comparable with that of the corresponding cyclopentene.Incorporation of ester units in the connecting unit between the chromophores or on the ethene inhibits intramolecular cyclisation as does the presence of para OMe, CN, or COMe groups in 5-phenylpent-1-ene.In contrast reaction selectivity and efficiency are greatly promoted by ortho Me or OMe groups and the products reflect exlusive 1,3-cycloaddition.The presence of a para Me group in 5-phenylpent-1-ene leads to specific 2,6-intramolecular cyclisation but the reaction of the meta-Me derivative leads to four products derived from 1,3- and 1,5-intramolecular cycloaddition.The observations are discussed in terms of mechanisms of arene-ethene photoreactions and preferred conformations of the bichromophores.
