1012-72-2Relevant articles and documents
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Potts,Carpenter
, p. 663 (1939)
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van Tamelen et al.
, p. 6092,6099 (1971)
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Malishev
, p. 883 (1935)
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Kelly,Lee
, p. 757,759 (1955)
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Craig
, p. 195,196 (1935)
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Hennion,Kurtz
, p. 1001 (1943)
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Myhre et al.
, p. 3425 (1966)
Franck,Yanagi
, p. 5814 (1968)
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Grosse,Ipatieff
, (1936)
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Radical aromatic substitution with benzene chromiumtricarbonyl
Byers, Jeffrey H.,Neale, Nathan R.,Bradford Alexander,Gangemi, Stephen P.
, p. 7903 - 7905 (2007)
Radical aromatic substitution of tert-butyl groups for hydrogen on simple arene chromiumtricarbonyl complexes was accomplished. Preexisting tert-butyl groups and methoxy groups directed incoming radicals primarily to the meta-position, and methoxy groups diminished the rate of substitution by roughly tenfold.
TRANSBUTYLATION OF AROMATIC HYDROCARBONS BY 3,6-DI-tert-BUTYLPYROCATECHOL IN PRESENCE OF SULFURIC ACID
Vol'eva, V. B.,Novikova, I. A.,Belostotskaya, I. S.,Komissarova, N. L.,Ershov, V. V.
, p. 1748 - 1750 (1981)
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Bryce-Smith,Owen
, p. 3319,3323 (1960)
Dual Nickel/Photoredox-Catalyzed Deaminative Cross-Coupling of Sterically Hindered Primary Amines
Dorsheimer, Julia R.,Ashley, Melissa A.,Rovis, Tomislav
supporting information, p. 19294 - 19299 (2021/11/23)
We report a method to activate α-3° amines for deaminative arylation via condensation with an electron-rich aldehyde and merge this reactivity with nickel metallaphotoredox to generate benzylic quaternary centers, a common motif in pharmaceuticals and natural products. The reaction is accelerated by added ammonium salts. Evidence is provided in support of two roles for the additive: inhibition of nickel black formation and acceleration of the overall reaction rate. We demonstrate a robust scope of amine and haloarene coupling partners and show an expedited synthesis of ALK2 inhibitors.
Silylium-arene adducts: An experimental and theoretical study
Ibad, Muhammad Farooq,Langer, Peter,Schulz, Axel,Villinger, Alexander
supporting information; experimental part, p. 21016 - 21027 (2012/03/07)
The solvent-coordinated [Me3Si·arene][B(C 6F5)4] salts (arene = benzene, toluene, ethylbenzene, n-propylbenzene, isopropylbenzene, o-xylene, m-xylene, p-xylene, 1,2,3-trimethylbenzene, 1,2,4-trimethylbenzene, 1,3,5-trimethylbenzene) are prepared and fully characterized. As an interesting decomposition product the formation of bissilylated fluoronium ion [Me3Si-F-SiMe 3]+ was observed and even cocrystallized with [Me 3Si·arene][B(C6F5)4] (arene = benzene and toluene). Investigation of the degradation of [Me 3Si·arene][B(C6F5)4] reveals the formation of fluoronium salt [Me3Si-F-SiMe3][B(C 6F5)4], B(C6F5) 3, and a reactive "C6F4" species which could be trapped with CS2. Upon addition of CS2, the formation of a formal S-heterocyclic carbene adduct, C6F 4CS2-B(C6F5)3, was observed. The structure and bonding of substituted [Me3Si· arene][B(C6F5)4] with arene = R nC6H6-n (R = H, Me, Et, Pr, and Bu; n = 0-6) is discussed on the basis of experimental and theoretical data. X-ray data of [Me3Si·arene][B(C6F5)4] salts reveal nonplanar arene species with significant cation...anion interactions. As shown by different theoretical approaches (charge transfer, partial charges, trimethylsilyl affinity values) stabilizing inductive effects occur; however, the magnitude of such effects differs depending on the degree of substitution and the substitution pattern.
Nickel-catalyzed cross-coupling of aryl bromides with tertiary grignard reagents utilizing donor-functionalized N-heterocyclic carbenes (NHCs)
Lohre, Claudia,Droege, Thomas,Wang, Congyang,Glorius, Frank
supporting information; experimental part, p. 6052 - 6055 (2011/06/25)
Metal-catalyzed cross-coupling reactions are among the most important transformations in organic synthesis, allowing the efficient construction of complex structures from simpler, readily available building blocks.Many applications in large and small-scale synthesis can be found in different areas such as agrochemicals, pharmaceuticals and supramolecular chemistry. Whereas the coupling of sp2-hybridized carbon atoms in either reaction partner is well established, the use of CACHTUNGTRENUNG(sp3)-hybridized substrates presents some challenges. Catalytic cross-coupling of sterically hindered tertiary alkyl substrates is especially difficult, generally resulting in low yields, and thus, only few reports exist.[27] A big challenge in this field is not only to get the required level of reactivity, but also to overcome competing pathways like β-hydride elimination, hydrodehalogenation or isomerization