7283-49-0Relevant academic research and scientific papers
MnBr2 catalyzed regiospecific oxidative Mizoroki-Heck type reaction
Chen, Xiang,Chen, Yi-Hung,Liu, Shanshan,Shen, Xiao,Zhu, Zhihong
, (2021/11/27)
Herein, we report an unprecedented regiospecific oxidative Mizoroki-Heck type reaction for the synthesis of ɑ-difluoromethyl homoallylic alcohols. The reaction shows broad substrate scopes and high functional group tolerance. Late-stage functionalization of complex biologically active molecules demonstrates the synthetic potential of this transformation. Mechanistic study supports the involvement of MnBr2 catalyzed radical 1,2-silyl transfer.
Dimerization of Benzyl and Allyl Halides via Photoredox-Mediated Disproportionation of Organozinc Reagents
Levin, Vitalij V.,Agababyan, Daniil P.,Struchkova, Marina I.,Dilman, Alexander D.
, p. 2930 - 2935 (2018/05/28)
Benzyl and allyl halides undergo homocoupling when treated with zinc in the presence of a catalytic amount of a cationic iridium(III) complex under irradiation with 400 nm light-emitting diodes. The reaction proceeds through the intermediate formation of an organozinc reagent, which disproportionates to a free radical and elemental zinc under photoredox conditions.
Nickel-Catalyzed Reductive Allylation of Tertiary Alkyl Halides with Allylic Carbonates
Chen, Haifeng,Jia, Xiao,Yu, Yingying,Qian, Qun,Gong, Hegui
supporting information, p. 13103 - 13106 (2017/09/19)
The construction of all C(sp3) quaternary centers has been successfully achieved under Ni-catalyzed cross-electrophile coupling of allylic carbonates with unactivated tertiary alkyl halides. For allylic carbonates bearing C1 or C3 substituents, the reaction affords excellent regioselectivity through the addition of alkyl groups to the unsubstituted allylic carbon terminus. The allylic alkylation method also exhibits excellent functional-group compatibility, and delivers the products with high E selectivity.
Synthesis of 2,5-Diaryl-1,5-dienes from Allylic Bromides Using Visible-Light Photoredox Catalysis
Pratsch, Gerald,Overman, Larry E.
, p. 11388 - 11397 (2015/12/01)
Visible-light photoreductive coupling of 2-arylallyl bromides in the presence of the photocatalyst Ru(bpy)3(PF6)2, a Hantzsch ester, and i-Pr2NEt gives 2,5-diaryl-1,5-dienes in high yield. This method avoids the use of stoichiometric metal reductants and is compatible with the presence of halogen, alkyl, electron-donating, and electron-withdrawing substituents on the aromatic ring.
A synthesis of allylboronates via the palladium(0)-catalyzed cross-coupling reaction of bis(pinacolato)diboron with allylic acetates
Ishiyama, Tatsuo,Ahiko, Taka-Aki,Miyaura, Norio
, p. 6889 - 6892 (2007/10/03)
The cross-coupling reaction of bis(pinacolato)diboron [(Me4C2O2)BB(O2C2Me4)] with allyl acetates regio- and E-stereoselectively provided the pinacol esters of allylboronic acids in high yields. The reaction was efficiently catalyzed by Pd[dba]2 in DMSO at 50°C.
Flash Vacuum Thermolysis of Phenylcyclopropanecarbaldoximes and Its Methyl Ethers
Wu, Pei-Lin,Wang, Wen-Shan,Chen, Chang-Fu
, p. 601 - 604 (2007/10/03)
Flash vacuum thermolysis of 1-phenylcyclopropane-1-carbaldoxime at 500 deg C produced mainly 3-phenylpyrrole.The products after thermolysis of its oxime methyl ether were α-methoxymethylstyrene, α-methylstyrene, and a dimer 2,5-diphenyl-1,5-hexadiene. - Key Words Flash vacuum thermolysis; 3-Phenylpyrrole; Phenylcyclopropanecarbaldoxime; Phenylcyclopropanecarbaldoxime methyl ether.
THE TITANOCENE METHYLENE-ZINC HALIDE COMPLEX: A CONVENIENT SYNTHESIS AND ITS METHYLENATING ACTION ON UNSATURATED CARBON CENTERS
Eisch, John J.,Piotrowski, Andrzej
, p. 2043 - 2046 (2007/10/02)
The titanocene methylene-zinc halide complex, which can be conveniently prepared by treating titanocene dichloride with methylenezinc iodide in THF solution, readily methylenates ketones, nitriles, and alkynes.
Cyclopropene Photochemistry. Mechanistic and Exploratory Organic Photochemistry
Zimmerman, Howard E.,Bunce, Richard A.
, p. 3377 - 3396 (2007/10/02)
Four new cyclopropenes have been synthesized and their photochemistry has been investigated.Thus, 3-methyl-1,2-diphenyl-3-(2-phenylallyl)cyclopropene was found on direct photolysis to afford four photoproducts, the two major products of which derived from novel photochemistry. 2-Methylene-4-methyl-5,6-diphenyltetracyclo1,504,6>undeca-8,10-diene derived from cycloaddition of the excited cyclopropenyl ? bond to the C-1,C-2 ? bond of the phenyl of the 2-phenylallyl side chain.The quantum yield for this novel transformation was 0.023.A second photoproduct was 2-methyl-1,4,6-triphenyltricyclo2,6>hexane.This product results from a formal cycloaddition of the excited cyclopropenyl ? bond to the allyl double bond.A diradical mechanism is structurally equivalent.Formation of such a tricyclic 2,6> system is normally not found in direct irradiations.The quantum yield for this product was 0.088.Also formed was 3-methyl-1,2,5-triphenylbicyclohex-2-ene with an efficiency of 0.019.This product is understood as deriving either (i) from cyclopropene opening to a carbene which then adds to the allyl ? bond or (ii) from a bicyclic diradical arising from vinyl-vinyl bonding.The fourth photoproduct is 2-methyl-1,3-diphenyl-3-(2-phenylallyl)cyclopropene.The efficiency was 0.018.The bicyclic diradical above provides a common species leading to the last three products.Sensitization led only to the first two products: the tetracyclic diene (φ=0.26) and the tricyclo2,6>hexane (φ=0.15).Product structures were established by X-ray, degradation, independent synthesis, and spectral analysis.In addition, the photochemistry of cis- and trans-2,6-dimethyl-1,6-diphenylspirooct-1-ene was investigated.Stereoisomerization resulted from the singlet but not the triplet.Mechanisms for the above transformations are considered.Finally, corresponding thermal chemistry exhibited by the above compounds was investigated.
EFFICIENT PREPARATION OF ALLYLIC GRIGNARD REAGENTS USING SLURRIES OF PRECONDENSED MAGNESIUM
Oppolzer, Wolfgang,Kuendig, Ernest Peter,Bishop, Paul M.,Perret, Celia
, p. 3901 - 3904 (2007/10/02)
Using a simple apparatus addition of 2-alkenyl halides to precondensed active Mg in THF gave clean solutions of 2-alkenylmagnesium halides which on carbonation furnished β,γ-unsaturated carboxylic acid in high yields.
