- Carboxylation of Aromatic and Aliphatic Bromides and Triflates with CO2 by Dual Visible-Light–Nickel Catalysis
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We report the efficient carboxylation of bromides and triflates with K2CO3 as the source of CO2 in the presence of an organic photocatalyst in combination with a nickel complex under visible light irradiation at room temperature. The reaction is compatible with a variety of functional groups and has been successfully applied to the synthesis and derivatization of biologically active molecules. In particular, the carboxylation of unactivated cyclic alkyl bromides proceeded well with our protocol, thus extending the scope of this transformation. Spectroscopic and spectroelectrochemical investigations indicated the generation of a Ni0 species as a catalytic reactive intermediate.
- Meng, Qing-Yuan,Wang, Shun,K?nig, Burkhard
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supporting information
p. 13426 - 13430
(2017/10/07)
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- 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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p. 7504 - 7507
(2016/07/06)
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- Method for Producing Isononanoic Acid Esters, Starting from 2-Ethyl Hexanol
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A Process for preparing carboxylic esters of a mixture of structurally branched C9 monocarboxylic acids proceeding from 2-ethylhexanol is characterized in that (a) 2-ethylhexanol is dehydrated to an octene mixture in the presence of a catalyst; (b) the octene mixture obtained in step a) is reacted in the presence of a transition metal compound of group VIII of the periodic table of the elements with carbon monoxide and hydrogen to give a mixture of isomeric isononanals; (c) the mixture of isomeric isononanals obtained in step b) is oxidized to a mixture of structurally branched C9 monocarboxylic acids; and (d) the mixture of structurally branched C9 monocarboxylic acids obtained in step c) is reacted with alcohols to give carboxylic esters.
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Paragraph 0081-0087
(2015/06/17)
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- Method for Producing Isononanoic Acids from 2-Ethyl Hexanol
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Process for preparing isononanoic acid proceeding from 2-ethylhexanol, characterized in that (a) 2-ethylhexanol is dehydrated to octene in the presence of a catalyst; (b) the octene obtained in step a) is reacted in the presence of a transition metal compound of group VIII of the periodic table of the elements with carbon monoxide and hydrogen to give isononanal; and (c) the isononanal obtained in step b) is oxidized to isononanoic acid.
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Paragraph 0062-0071
(2015/07/15)
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- Zirconocene-catalyzed sequential ethylcarboxylation of alkenes using ethylmagnesium chloride and carbon dioxide
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The zirconocene-catalyzed sequential ethylcarboxylation of alkenes using ethylmagnesium chloride and carbon dioxide has been developed. A range of alkenes were transformed into the corresponding carboxylic acids in high yields.
- Shao, Peng,Wang, Sheng,Chen, Chao,Xi, Chanjuan
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supporting information
p. 6640 - 6642
(2015/04/14)
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- Ni-catalyzed carboxylation of unactivated primary alkyl bromides and sulfonates with CO2
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A Ni-catalyzed carboxylation of unactivated primary alkyl bromides and sulfonates with CO2 at atmospheric pressure is described. The method is characterized by its mild conditions and remarkably wide scope without the need for air- or moisture-sensitive reagents, which make it a user-friendly and operationally simple protocol en route to carboxylic acids.
- Liu, Yu,Cornella, Josep,Martin, Ruben
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supporting information
p. 11212 - 11215
(2014/09/30)
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- Phenylglycine methyl ester, a useful tool for absolute configuration determination of various chiral carboxylic acids
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A new chiral anisotropic reagent, phenylglycine methyl ester (PGME), developed for the elucidation of the absolute configuration of chiral α,α- disubstituted acetic acids, has turned out to be applicable to other substituted carboxylic acids, such as chiral α-hydroxy-, α-alkoxy-, and α- acyloxy-α,α-disubstituted acetic acids, as well as to chiral β,β- disubstituted propionic acids. Because a carboxylic moiety is convertible from other functional groups, e.g., ozonolysis of an olefin and oxidative cleavage of a glycol, the present findings can expand the utility of the PGME method to the absolute configuration determination of various types of organic compounds, even those which initially lack oxygen functions. Several examples of the combination of chemical reactions and the PGME method are described.
- Yabuuchi, Tetsuya,Kusumi, Takenori
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p. 397 - 404
(2007/10/03)
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- Conjugate addition of organolithium reagents to α,β-unsaturated carbocyclic acids
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Conjugate addition of primary, secondary, tertiary alkyi and phenyl lithium reagents to 2-alkenoic acids affords good yields of branched saturated carboxylic acids. Methyl groups at the α- and β-carbon of the 2-alkenoic acid decrease reactivity as acceptors, and foster deprotonation, respectively. The lithium enediolate resulting from the conjugate addition can react with electrophiles. PM3 calculations are in agreement with the substituent effects.
- Aurell, Maria Jose,Domingo, Luis Ramon,Mestres, Ramon,Munos, Elena,Zaragoza, Ramon Jose
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p. 815 - 830
(2007/10/03)
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- Conjugate addition of organolithium reagents to α,β- unsaturated carboxylic acids
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Conjugate addition of primary, secondary, tertiary alkyl and phenyl lithium reagents to 2-alkenoic acids affords good yields of branched saturated carboxylic acids. Substitution by methyl groups at the α-carbon strongly decreases reactivity, whereas deprotonation of the starting acid occurs almost exclusively with methyl substitution at the β-carbon of the 2- alkenoic acid.
- Aurell, Maria Jose,Mestres, Ramon,Munoz, Elena
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p. 6351 - 6354
(2007/10/03)
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