- Ni-Catalyzed Carboxylation of Unactivated Alkyl Chlorides with CO2
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A catalytic carboxylation of unactivated primary, secondary, and tertiary alkyl chlorides with CO2 at atmospheric pressure is described. This protocol represents the first intermolecular cross-electrophile coupling of unactivated alkyl chlorides, thus leading to new knowledge in the cross-coupling arena.
- B?rjesson, Marino,Moragas, Toni,Martin, Ruben
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supporting information
p. 7504 - 7507
(2016/07/06)
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- The carboxylation of saturated hydrocarbons by Gif systems (Fe0/CO/O2 and Cu0/CO/O2 in pyridine-acetic acid)
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Saturated hydrocarbons are transformed into the corresponding homologous carboxylic acid by treatment with Fe0/CO/O2 or Cu0/CO/O2 in pyridine/acetic acid. Mechanistic studies support a reaction pathway involving the insertion of CO into a carbon-iron or carbon-copper bond.
- Barton,Csuhai,Doller
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p. 4389 - 4392
(2007/10/02)
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- Functionalization of Saturated Hydrocarbons. 14. Further Studies on the Mechanism of Gif-Type Systems
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The photolysis (W light) of acyl derivatives of N-hydroxy-2-thiopyridone in pyridine-acetic acid permits a study of the partioning of secondary radicals between oxygen, pyridine, and the thione function.Comparison with the GifIV oxidation system for saturated hydrocarbons confirms that radicals are not involved in oxidation at secondary positions.On the contrary, radical behavior at the tertiary position in adamantane is again established.The two recently introduced Gif-type systems, GoAggI and GoAggII, have been shown to give the same overall selectivity in attack on adamantane with the usual coupling of the tertiary radical with pyridine.
- Barton, Derek H. R.,Halley, Frank,Ozbalik, Nubar,Schmitt, Martine,Young, Esme,Balavoine, Gilbert
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p. 7144 - 7149
(2007/10/02)
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- The Regiospecific Palladium Catalysed Hydrocarboxylation of Alkenes under Mild Conditions
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Alkenes react with carbon monoxide, water, oxygen, hydrochloric acid, and palladium and copper chlorides, to give branched chain acids in good yields.
- Alper, Howard,Woell, James B.,Despeyroux, Bertrand,Smith, David J. H.
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p. 1270 - 1271
(2007/10/02)
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- Oxy-Cope Rearrangement Route to Bridgehead Olefins
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Bicyclic bridgehead olefins, with a carbonyl group included in the largest bridge, may be synthesized by oxy-Cope rearrangement of easily accessible spirocyclic precursors.
- Levine, Samuel G.,McDaniel, Roger L.
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p. 2199 - 2200
(2007/10/02)
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- Crown Cation Complex Effects. 10. Potassium tert-Butoxide Mediated Penultimate Oxidative Hydrolysis of Nitriles
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The failure of phase-transfer catalysis to improve either the yield or rapidity of basic nitrile hydrolysis is due, in part, to the poor solubility of quaternary ammonium hydroxides in nonpolar solutions.An alternative hydrolysis method which involves potassium tert-butoxide mediated oxidative cleavage of the nitrile with loss of the cyano carbon is presented.The isolated yields reported here range from 21-93percent and are found to be highest for long-chain aliphatic nitriles such as cyanohexadecane.
- DiBiase, Stephen A.,Wolak, Raymond P.,Dishong, Dennis M.,Gokel, George W.
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p. 3630 - 3634
(2007/10/02)
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