30984-53-3Relevant academic research and scientific papers
Markovnikov Wacker-Tsuji Oxidation of Allyl(hetero)arenes and Application in a One-Pot Photo-Metal-Biocatalytic Approach to Enantioenriched Amines and Alcohols
Albarrán-Velo, Jesús,Gotor-Fernández, Vicente,Lavandera, Iván
supporting information, p. 4096 - 4108 (2021/08/19)
The Wacker-Tsuji aerobic oxidation of various allyl(hetero)arenes under photocatalytic conditions to form the corresponding methyl ketones is presented. By using a palladium complex [PdCl2(MeCN)2] and the photosensitizer [Acr-Mes]ClO4 in aqueous medium and at room temperature, and by simple irradiation with blue led light, the desired carbonyl compounds were synthesized with high conversions (>80%) and excellent selectivities (>90%). The key process was the transient formation of Pd nanoparticles that can activate oxygen, thus recycling the Pd(II) species necessary in the Wacker oxidative reaction. While light irradiation was strictly mandatory, the addition of the photocatalyst improved the reaction selectivity, due to the formation of the starting allyl(hetero)arene from some of the obtained by-products, thus entering back in the Wacker-Tsuji catalytic cycle. Once optimized, the oxidation reaction was combined in a one-pot two-step sequential protocol with an enzymatic transformation. Depending on the biocatalyst employed, i. e. an amine transaminase or an alcohol dehydrogenase, the corresponding (R)- and (S)-1-arylpropan-2-amines or 1-arylpropan-2-ols, respectively, could be synthesized in most cases with high yields (>70%) and in enantiopure form. Finally, an application of this photo-metal-biocatalytic strategy has been demonstrated in order to get access in a straightforward manner to selegiline, an anti-Parkinson drug. (Figure presented.).
Palladium-Catalyzed Oxidative Allylation of Sulfoxonium Ylides: Regioselective Synthesis of Conjugated Dienones
Li, Chunsheng,Li, Meng,Zhong, Wentao,Jin, Yangbin,Li, Jianxiao,Wu, Wanqing,Jiang, Huanfeng
supporting information, p. 872 - 875 (2019/05/16)
The first examples of palladium-catalyzed allylic C-H oxidative allylation of sulfoxonium ylides to afford the corresponding conjugated dienones with moderate to good yields have been established. The features of this novel conversion include mild reaction conditions, wide substrate scope, and excellent regioselectivity.
Palladium-catalyzed oxidative allylation of bis[(pinacolato)boryl]methane: Synthesis of homoallylic boronic esters
Li, Chunsheng,Li, Meng,Li, Jianxiao,Wu, Wanqing,Jiang, Huanfeng
supporting information, p. 66 - 69 (2017/12/27)
A palladium-catalyzed oxidative allylation of bis[(pinacolato)boryl]methane to afford the corresponding homoallylic organoboronic esters with moderate to excellent yields is reported. This novel transformation provides an efficient strategy for the construction of homoallylic organoboronic esters in one step with a broad substrate scope. It is proposed that the palladium-catalyzed oxidative allylic C-H bond activation process may be involved in the catalytic cycle.
Direct conversion of allyl arenes to aryl ethylketones via a TBHP-mediated palladium-catalyzed tandem isomerization-Wacker oxidation of terminal alkenes
Zhao, Jinwu,Liu, Li,Xiang, Shijian,Liu, Qiang,Chen, Huoji
supporting information, p. 5613 - 5616 (2015/05/27)
A TBHP-mediated palladium-catalyzed tandem isomerization-Wacker oxidation of terminal alkenes was developed. This methodology provides a new efficient and simple route for conversion of a range of allyl arenes directly into aryl ethylketones in good yields with high chemoselectivity.
Cascade multicomponent synthesis of indoles, pyrazoles, and pyridazinones by functionalization of alkenes
Matcha, Kiran,Antonchick, Andrey P.
supporting information, p. 11960 - 11964 (2015/01/09)
The development of multicomponent reactions for indole synthesis is demanding and has hardly been explored. The present study describes the development of a novel multicomponent, cascade approach for indole synthesis. Various substituted indole derivative
New fluorine substituted liquid crystal containing bicyclo[2.2.2]octane unit
Geivandov,Mezhnev,Geivandova
experimental part, p. 106 - 114 (2012/01/17)
We have designed and synthesized a new series of liquid crystalline compounds with hybridized three-ring system based on bicyclo[2.2.2]octane unit together with fluorine substituted phenyl and biphenyl fragments. The key stages of the synthesis are alkyla
Design, synthesis and cytotoxicity of 7-deoxy aryl discodermolide analogues
Burlingame, Mark A.,Shaw, Simon J.,Sundermann, Kurt F.,Zhang, Dan,Petryka, Joseph,Mendoza, Esteban,Liu, Fenghua,Myles, David C.,LaMarche, Matthew J.,Hirose, Tomoyasu,Freeze, B. Scott,Smith III, Amos B.
, p. 2335 - 2338 (2007/10/03)
A series of 7-deoxy discodermolide analogues in which the lactone fragment 'C' was replaced by aryl substituents were designed, synthesized, and evaluated for cytotoxicity.
Structure of ω-Arylalkyl Radicals: A 13C CIDNP Investigation
Olah, George A.,Krishnamurthy, V. V.,Singh, Brij P.,Iyer, Pradeep S.
, p. 955 - 963 (2007/10/02)
Thermolysis of a series of ω-arylalkanoyl m-chlorobenzoyl (and acetyl) peroxides at ca. 100 deg C in cyclohexanone and in hexachloroacetone was studied by using 13C chemically induced dynamic nuclear polarization.Analysis of the observed 13C polarizations indicate that all the three radicals (β-arylethyl, γ-arylpropyl and δ-arylbutyl) have open-chain structures with no evidence for aryl participation resulting in spirocycloalkylcyclohexadienyl radicals.
