- Pd-catalyzed C4-Dearomative Allylation of Benzyl Ammoniums with Allyltributylstannane
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A dearomative C4-allylation of benzyl ammoniums with allyltributylstannane by a palladium catalysis is described. A triarylphosphine-ligated palladium catalyst, which is capable of cleaving benzylic CN bonds, realized facile dearomative reactions with C4 selectivity. Combined with precedented C2- A nd C3-selective functionalizations of benzyl amine derivatives, the present reaction can provide a new synthetic option for the synthesis of multi-substituted alicyclic compounds as well as aromatic compounds.
- Kayashima, Yuki,Komatsuda, Masaaki,Muto, Kei,Yamaguchi, Junichiro
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supporting information
p. 836 - 839
(2020/07/23)
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- 187. Acid-Catalyzed Cleavage of 1,4-Dimethyl-1,4-dihydronaphthalene 1,4-Endoperoxide. Reactivity of the Resulting Hydroxyperoxy Carbocation with Nucleophiles
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In the presence of acids, 1,4-dimethyl-1,4-dihydronaphthalene 1,4-endoperoxie readily reacts with nucleophiles to produce methyl- and ring-substituted naphthalenes in high yields.The regioselectivity observed depends on the nucleophile.The key intermediate is shown to be the corresponding hydroperoxy carbocation which could be intercepted in certain cases prior to aromatization.The hydroperoxide also undergoes Hock-type cleavage and dimerization giving 2,3-dihydro-1-benzoxepins, 4-methyl-1-naphthol, and 1,2,5,6-tetraoxocane as by-products.
- Jefford, Charles W.,Rossier, Jean-Claud,Kohmoto, Shigeo,Boukouvalas, John
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p. 1804 - 1814
(2007/10/02)
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- Functionalization of the Methyl Group of 1,4-Dimethyl-1,4-dihydronaphthalene-1,4-endoperoxide
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The acid-catalysed cleavage of 1,4-dimethyl-1,4-dihydronaphthalene-1,4-endoperoxide gives the 4-hydroxy, methoxy, trifluoroacetoxy, formyloxy, bromo, and chloro methyl derivatives of 1-methylnaphthalene in yields of 36, 38, 52, 76, 77, and 100percent respectively when water, methanol, trifluoroacetic, formic, hydrobromic, or hydrochloric acids are used as reagents.
- Jefford, Charles W.,Rossier, Jean-Claude,Kohmoto, Shigeo,Boukouvalas, John
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p. 1496 - 1497
(2007/10/02)
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