- Anti-Markovnikov Hydroheteroarylation of Unactivated Alkenes with Indoles, Pyrroles, Benzofurans, and Furans Catalyzed by a Nickel-N-Heterocyclic Carbene System
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We report the catalytic addition of C-H bonds at the C2 position of heteroarenes, including pyrroles, indoles, benzofurans, and furans, to unactivated terminal and internal alkenes. The reaction is catalyzed by a combination of Ni(COD)2 and a sterically hindered, electron-rich N-heterocyclic carbene ligand or its analogous Ni(NHC)(arene) complex. The reaction is highly selective for anti-Markovnikov addition to α-olefins, as well as for the formation of linear alkylheteroarenes from internal alkenes. The reaction occurs with substrates containing ketones, esters, amides, boronate esters, silyl ethers, sulfonamides, acetals, and free amines.
- Schramm, York,Takeuchi, Makoto,Semba, Kazuhiko,Nakao, Yoshiaki,Hartwig, John F.
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supporting information
p. 12215 - 12218
(2015/10/12)
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- Synthesis and Characterisation of some 1,4,8,11,15,18,22,25-Octa-alkyl- and 1,4,8,11,15,18-Hexa-alkyl-22,25-bis(carboxypropyl)phthalocyanines
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A series of 3,6-dialkylphthalonitriles and 3,6-bis(4,4,4-trimethoxybutyl)phthalonitrile have been prepared via Diels-Alder reactions of 2,5-disubstituted furans or thiophene 1,1-dioxides with fumaronitrile.The phthalonitriles were converted into the title phthalocyanines as metal-free and copper(II) derivatives.The macrocycles were characterised using 1H NMR and optical spectroscopy, and fastatom bombardment spectrometry.Certain examples exhibit discotic liquid crystal behaviour.
- McKeown, Neil B.,Chambrier, Isabelle,Cook, Michael J.
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p. 1169 - 1177
(2007/10/02)
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- A FACILE ROUTE TO 5-ALKYL-2(3H)-FURANONES BY PHOTOISOMERISATION OF ENEDICARBONYL COMPOUNDS
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A new and useful synthesis of a title compounds is reported.They can be obtained easily by photocyclization of enedicarbonyl compounds 3 and 4.A different behaviour, ascribed to the geometry of a double bond, is observed; 3 are converted only to butenolides 5, while trans-isomers 4 are converted into alkyl-furyl-ketones 5 and 6.A possible mechanism is described.
- Auria, M. D',Mico, A. De,Piancatelly, G.,Scettry, A.
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p. 1661 - 1666
(2007/10/02)
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