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.
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
Alkylation of pyrocatechol in tert-butyl alcohol-sulfuric acid-benzene
Vol'eva,Prokof'eva,Belostotskaya,Komissarova,Gorbunov,Kurkovskaya
experimental part, p. 1310 - 1312 (2011/12/05)
Alkylation of pyrocatechol with tert-butyl alcohol in benzene in the presence of sulfuric acid gave 3,5-di-tert-butylbenzene-1,2-diol in a higher yield than in analogous reaction with tert-butyl alcohol. This result was rationalized by reduction of inhibitory effect of liberated water, formation of heterogeneous system, and occurrence of the alkylation process in nonpolar organic phase. Intermediate products were identified and found to undergo intra- and intermolecular tert-butyl group transfer with formation of more stable 3,5-di-tert-butylbenzene-1,2-diol. The formation of p-di-tert-butylbenzene indicated participation of benzene in crossalkylation processes. Pleiades Publishing, Ltd., 2011.