cas 1737-16-2, 3-(4-FLUOROPHENYL)-1-PROPENE

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Manganese catalyzed dehydrogenative silylation of alkenes: Direct access to allylsilanes
Dehydrogenative silylation of alkenes with silanes to produce allylsilanes is achieved through manganese catalysis with a wide scope of substrate tolerance. This transformation involves silane radicals initiated by manganese complex without additional oxidant additives. It offers a general, convenient and practical protocol with excellent functional group compatibility and gram-scale capacity for the modular synthesis of allylsilanes.
Wu, Shang,Zhang, Ying,Jiang, Hongyan,Ding, Ning,Wang, Yanbin,Su, Qiong,Zhang, Hong,Wu, Lan,Yang, Quanlu
supporting information

(2020/06/03)

Controllable, Sequential, and Stereoselective C-H Allylic Alkylation of Alkenes
The direct conversion of C-H bonds into new C-C bonds represents a powerful approach to generate complex molecules from simple starting materials. However, a general and controllable method for the sequential conversion of a methyl group into a fully substituted carbon center remains a challenge. We report a new method for the selective and sequential replacement of three C-H bonds at the allylic position of propylene and other simple terminal alkenes with different carbon groups derived from Grignard reagents. A copper catalyst and electron-rich biaryl phosphine ligand facilitate the formation of allylic alkylation products in high branch selectivity. We also present conditions for the generation of enantioenriched allylic alkylation products in the presence of catalytic copper and a chiral phosphine ligand. With this approach, diverse and complex products with substituted carbon centers can be generated from simple and abundant feedstock chemicals.
Qin, Ling,Sharique, Mohammed,Tambar, Uttam K.
supporting information
p. 17305 - 17313
(2019/11/03)

Palladium-Catalyzed Oxidative Allylation of Sulfoxonium Ylides: Regioselective Synthesis of Conjugated Dienones
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.
Li, Chunsheng,Li, Meng,Zhong, Wentao,Jin, Yangbin,Li, Jianxiao,Wu, Wanqing,Jiang, Huanfeng
supporting information
p. 872 - 875
(2019/05/16)

Palladium-catalyzed allylic C-H oxidation under simple operation and mild conditions
We discovered an effective and simple system (Pd/BQ/air/r.t.) for making allylic alcohols through Pd-catalyzed allylic C-H bond functionalization. This approach exhibits advantages due to its simple operation, mild conditions, and environmentally benign features. By modifying reaction conditions, it can be suitable for preparing unsaturated aldehydes, allylic esters, ethers, and amines.
Guo, Yunlong,Shen, Zengming
supporting information
p. 3103 - 3107
(2019/03/26)

Palladium-catalyzed oxidative allylation of bis[(pinacolato)boryl]methane: Synthesis of homoallylic boronic esters
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.
Li, Chunsheng,Li, Meng,Li, Jianxiao,Wu, Wanqing,Jiang, Huanfeng
supporting information
p. 66 - 69
(2017/12/27)

Anti-Markovnikov rearrangement in sulfur mediated allylic C-H amination of olefins
Cationic rearrangement reactions usually follow Markovnikov's rule to give more substituted carbocations as stable intermediates. During our study on sulfur mediated allylic C-H amination of olefins, very rare cases of anti-Markovnikov rearrangement from secondary carbocations toward primary carbocations or primary triflates were observed.
Zhang, Zhong,Du, Hongguang,Xu, Jiaxi,Li, Pingfan
supporting information
p. 11547 - 11550
(2016/10/03)

Palladium-catalyzed aerobic oxidative double allylic C-H oxygenation of alkenes: A novel and straightforward route to α,β-unsaturated esters
A mild tandem oxidative functionalization of allyl aromatic hydrocarbons was accomplished using the catalytic system of Pd(OAc)2/DMA under 1 atm O2. The green twofold C-O bond formation involving double allylic C-H oxygenation unlocks opportunities for markedly different synthetic strategies. Moreover, the reaction affords aryl α,β-unsaturated esters directly from readily available terminal olefins in moderate to good yields with excellent chemo- and stereoselectivities.
Yang, Wanfei,Chen, Huoji,Li, Jianxiao,Li, Chunsheng,Wu, Wanqing,Jiang, Huanfeng
p. 9575 - 9578
(2015/06/08)

Trifluoromethylchlorosulfonylation of alkenes: Evidence for an inner-sphere mechanism by a copper phenanthroline photoredox catalyst
Abstract A visible-light-mediated procedure for the unprecedented trifluoromethylchlorosulfonylation of unactivated alkenes is presented. It uses [Cu(dap)2]Cl as catalyst, and contrasts with [Ru(bpy)3]Cl2, [Ir(ppy)2(dtbbpy)]PF6, or eosin Y that exclusively give rise to trifluoromethylchlorination of the same alkenes. It is assumed that [Cu(dap)2]Cl plays a dual role, that is, acting both as an electron transfer reagent as well as coordinating the reactants in the bond forming processes. Double role: The trifluoromethylchlorosulfonylation of unactivated alkenes was developed using [Cu(dap)2]Cl as catalyst (dap=2,9-bis(para-anisyl)-1,10-phenanthroline). [Cu(dap)2]Cl plays a dual role; acting as an electron transfer reagent as well as coordinating the reactants in the bond forming processes.
Bagal, Dattatraya B.,Kachkovskyi, Georgiy,Knorn, Matthias,Rawner, Thomas,Bhanage, Bhalchandra M.,Reiser, Oliver
supporting information
p. 6999 - 7002
(2015/06/08)

Direct conversion of allyl arenes to aryl ethylketones via a TBHP-mediated palladium-catalyzed tandem isomerization-Wacker oxidation of terminal alkenes
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.
Zhao, Jinwu,Liu, Li,Xiang, Shijian,Liu, Qiang,Chen, Huoji
supporting information
p. 5613 - 5616
(2015/05/27)

Ortho-allylation of 1-arylpyrazoles with allyl phenyl ether via iron-catalyzed C-H bond activation under mild conditions
An iron salt and a bipyridine-type ligand catalyze the ortho-allylation of 1-arylpyrazoles and congeners with allyl phenyl ether under mild conditions (0 °C). The ligand, an organozinc base, and the nature of the allylating reagent are crucial for the success of this reaction. Under these conditions, a competitive phenylation reaction is largely retarded, and cross-coupling of the organozinc with the allyl electrophile is minimized. The reaction may proceed via iron-catalyzed ortho C-H activation to form a metallic intermediate, which then reacts with the allyl ether in a γ selective fashion.
Asako, Sobi,Norinder, Jakob,Ilies, Laurean,Yoshikai, Naohiko,Nakamura, Eiichi
supporting information
p. 1481 - 1485
(2014/06/09)

Palladium-catalyzed regioselective azidation of allylic C-H bonds under atmospheric pressure of dioxygen
A palladium-catalyzed allylic azidation of alkenes with sodium azide under atmospheric pressure of dioxygen was developed. This methodology provides a new efficient and simple route for accessing allylic azides. Furthermore, the one-pot process consisting of Pd-catalyzed allylic azidation of alkenes and Cu-catalyzed 1,3-dipolar cycloaddition led directly to the 1,2,3-triazole from the alkene. The formed allylic azide can be also in situ reduced to the allylic amine or oxidized to the alkenyl nitrile. the Partner Organisations 2014.
Chen, Huoji,Yang, Wanfei,Wu, Wanqing,Jiang, Huanfeng
supporting information
p. 3340 - 3343
(2014/05/20)

Isomerizing ethenolysis as an efficient strategy for styrene synthesis
A shrinking chain: A bimetallic system consisting of [{Pd(μ-Br)(tBu 3P)}2] and a ruthenium metathesis catalyst has been found to efficiently promote the cross-metathesis between substituted alkenes and ethylene, while continuously migrating the double bond along the alkenyl chain (see scheme). When alkenylarenes, such as the natural products eugenol, safrol, or estragol, were treated with this catalyst under an ethylene atmosphere, they were cleanly converted into the corresponding styrenes and propylene gas. Copyright
Baader, Sabrina,Ohlmann, Dominik M.,Goossen, Lukas J.
supporting information
p. 9807 - 9810
(2013/08/23)

Method for Allylating and Vinylating Aryl, Heteroaryl, Alkyl, and Alkene Halogenides Using Transition Metal Catalysis
What is described is a process for preparing organic compounds of the general formula (I) R—R′??(I) by converting a corresponding compound of the general formula (II) R—X ??(II) in which X is fluorine, chlorine, bromine or iodine to an organomagnesium compound of the general formula (III) [M+]n[RmMgXkY1]??(III) wherein compounds of the formula (III) are reacted with a compound of the general formula (IV) characterized in that the reaction of (III) with (IV) is performed in the presence of a) catalytic amounts of an iron compound, based on the compound of the general formula (II), and optionally in the presence of b) a nitrogen-, oxygen- and/or phosphorus-containing additive in a catalytic or stoichiometric amount, based on the compound of the general formula (II).
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Paragraph 0062; 0063; 0064

(2013/07/25)

Highly regioselective palladium-catalysed oxidative allylic C-H carbonylation of alkenes
Pd-catalysed direct oxidative carbonylation of allylic C-H bonds with carbon monoxide was first described. This new procedure shows that the inherent requirement for a leaving group in the Tsuji-Trost palladium-catalysed allylic carbonylation can be lifted, which provides a new route for accessing more synthetically useful β-enoic acid esters with high regioselectivity. The Royal Society of Chemistry 2011.
Chen, Huoji,Cai, Congbi,Liu, Xiaohang,Li, Xianwei,Jiang, Huanfeng
supporting information; scheme or table
p. 12224 - 12226
(2011/12/14)

Practical iron-catalyzed allylations of aryl grignard reagents
An operationally simple iron-catalyzed reductive cross-coupling reaction between aryl halides and allyl electrophiles has been developed. The underlying domino process exhibits high versatility with respect to the allylic leaving group (acetate, tosylate, diethyl phosphate, methyl carbonate, trimethylsilanolate, methanethiolate, chloride, bromide) and high economic and environmental sustainability with respect to the catalyst system (0.2-5 mol% tris(acetylacetonato)iron(III), ligand-free) and reaction conditions (tetrahydrofuran, 0°C, 45 min).
Mayer, Matthias,Czaplik, Waldemar M.,Von Wangelin, Axel Jacobi
supporting information; experimental part
p. 2147 - 2152
(2010/12/18)

INHIBITORS OF JANUS KINASES
The instant invention provides for compounds that inhibit the four known mammalian JAK kinases (JAK1, JAK2, JAK3 and TYK2) and PDK1. The invention also provides for compositions comprising such inhibitory compounds and methods of inhibiting the activity of JAK1, JAK2, JAK3, TYK2 and PDK1 by administering the compound to a patient in need of treatment for myeloproliferative disorders or cancer.
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Page/Page column 43

(2010/01/12)

Stannylated polynorbornenes as new reagents for a clean stille reaction
New functionalized polynorbornenes have been obtained in good yields by vinylic copolymerization of norbornene with a (norbornenyl)Sn-Bu2Cl monomer, catalyzed by [Ni(C6F5)2(SbPh 3)2]. Subsequent functionalization produces a wide variety of polymers with different -SnBu2R groups (R = aryl, vinyl, alkynyl). The polymers can be used as R-transfer reagents in Stille couplings, thereby providing easy workup and separation of the polymeric tin byproducts from the coupling products. Tin contents of around 0.05 wt% are found in the Stille products. The stannylated polymers can be recycled and reused with good efficiency.
Carrera, Nora,Gutierrez, Enrique,Benavente, Rut,Villavieja, M. Mar,Albeniz, Ana C.,Espinet, Pablo
scheme or table
p. 10141 - 10148
(2009/11/30)

Catalytic intermolecular allylic C-H alkylation
The first electrophilic Pd(II)-catalyzed allylic C-H alkylation is reported, providing a novel method for formation of sp3-sp3 C-C bonds directly from C-H bonds. A wide range of aromatic and heteroaromatic linear (E)-α-nitro-arylpent
Young, Andrew J.,White, M. Christina
supporting information; experimental part
p. 14090 - 14091
(2009/03/11)

INHIBITORS OF JANUS KINASES
The instant invention provides for compounds that inhibit the four known mammalian JAK kinases (JAK1, JAK2, JAK3 and TYK2) and PDK1. The invention also provides for compositions comprising such inhibitory compounds and methods of inhibiting the activity of JAK1, JAK2, JAK3 TYK2 and PDK1 by administering the compound to a patient in need of treatment for myeloproliferative disorders or cancer.
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Page/Page column 78

(2009/01/23)

Allylation and vinylation of aryl radicals generated from diazonium salts
(Chemical Equation Presented) Allylation and vinylation of aryl radicals generated from aryl diazonium salts provides rapid and efficient access to chlorinated and brominated derivatives of styrene and allylbenzene. Allyl chlorides were found to be better substrates than bromides due to decreased halogen transfer. Donor- and acceptor-substituted diazonium salts are well tolerated. The products represent important precursors for numerous further transformations.
Heinrich, Markus R.,Blank, Olga,Ullrich, Daniela,Kirschstein, Marcel
p. 9609 - 9616
(2008/03/27)

Sodium dithionite initiated addition of 1-bromo-1-chloro-2,2,2-trifluoroethane to allylaromatics. Facile synthesis of conjugated dienes substituted with terminal CF3 group
Sodium dithionite effectively promotes the addition of 1-bromo-1-chloro-2,2,2-trifluoroethane to the terminal double bond of allylbenzenes 1. The reactions proceeded in MeCN/H2O to give a 3:1 mole ratio of diastereoisomers of 1-(2-bromo-4-chloro-5,5,5-trifluoropentyl)benzenes 2 as the main products together with small amounts of its reductive debromination products 3. Total yields of 2 and 3 were dependent on the nature of the aromatic ring substituents in 1. Treatment of adducts 2 with DBU in refluxing hexanes resulted in double dehydrohalogenation affording, in good yields, conjugated dienes 4 (1,1,1-trifluoro-5-phenyl-2,4-pentadienes) terminated with the CF3 group at the one end and the phenyl group at the opposite end. These dienes were found to be sufficiently reactive to undergo Diels-Alder condensation with active dienophiles to give trifluoromethylated carbocycles. The reactions of CF3CHClBr with allylheterocycles were less successful and lead to low yields of mixtures of hardly separable compounds or to polymeric resins.
Ignatowska, Jolanta,Dmowski, Wojciech
p. 720 - 729
(2008/03/28)

A highly effective (Triphenyl phosphite)palladium catalyst for a cross-coupling reaction of allylic alcohols with organoboronic acids
The cross coupling reaction of aryl and vinyl boronic acids and allylic alcohols proceeded smoothly in toluene or dioxane in the presence of a (triphenyl phosphite)palladium catalyst to give the corresponding allylbenzene derivatives and 1,4-dienes. Neither cocatalysts for promoting C-O bond cleavage of allylic alcohols nor bases for activation of organoboron reagents are required for promoting the coupling process. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.
Kayaki, Yoshihito,Koda, Takashi,Ikariya, Takao
p. 4989 - 4993
(2007/10/03)

Cobalt-catalyzed direct electrochemical cross-coupling between aryl or heteroaryl halides and allylic acetates or carbonates
The electroreduction of a mixture of functionalized aromatic or heteroaromatic bromides or chlorides and allylic compounds such as acetates or carbonates in an electrochemical cell fitted with a sacrificial iron anode affords, in the presence of cobalt halide associated with pyridine as ligand in acetonitrile or DMF, the corresponding coupling product in good yields.
Gomes, Paulo,Gosmini, Corinne,Perichon, Jacques
p. 1142 - 1145
(2007/10/03)

Structure of ω-Arylalkyl Radicals: A 13C CIDNP Investigation
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.
Olah, George A.,Krishnamurthy, V. V.,Singh, Brij P.,Iyer, Pradeep S.
p. 955 - 963
(2007/10/02)