22482-62-8Relevant articles and documents
A direct synthesis of carboxylic acidsviaplatinum-catalysed hydroxycarbonylation of olefins
Schneider, Carolin,Franke, Robert,Jackstell, Ralf,Beller, Matthias
, p. 2703 - 2707 (2021/05/05)
The platinum-catalysed hydroxycarbonylation of olefins is reported for the first time. Using a combination of PtCl2/2,2′-bis(tert-butyl(pyridin-2-yl)phosphanyl)-1,1′-binaphthalene (Neolephos) in the presence of sulfuric acid [0.6 M] in acetic acid selective carbonylation of terminal aliphatic olefins proceeds to good yields and selectivities to the corresponding carboxylic acids. Comparing the reactivity of different butenes (iso- andn-butenes), the terminal olefin can be selectively carbonylated.
Organoboranes. 35. Reaction of Alkylthioboronic Esters with Trichloromethyllithium: Preparation of One-Carbon-Extended Carboxylic Acids and Thioacetals from Alkenes via Hydroboration
Brown, Herbert C.,Imai, Toshiro
, p. 892 - 898 (2007/10/02)
Various 2-alkyl-1,3,2-dithiaborolanes, RB(S2C2H4) (1), were converted to the corresponding carboxylic acids, RCO2H (2), by using LiCCl3 in THF, followed by oxidation with alkaline hydrogen peroxide.For R=hexyl, a reaction intermediate is converted by solvent into another compound, C6H13C(S2C2H4)B2 (9a), characterized spectroscopically.The yields of 2 decreased with increasing bulkiness of the alkyl groups R.Although the configuration of R= trans-2-methylcyclopent-1-yl (1k) was retained in the product (>98percent trans), a significant degree of epimerization tookplace for R= exo-norbornyl (1j) during the oxidation (exo : endo = 86 : 14).More uniquely, the intermediates 9 were easily hydrolyzed by heating the reaction mixture with aqueous NaOH to give the corresponding 2-alkyl-1,3-dithiolanes 3.Stereochemical integrity was retained in the products derived from 1j and 1k.Since 1 was prepared by the hydroboration of alkenes, this sequence provides a new method for introducing oxycarbonyl or thioacetal functionality into alkenes in a regioselective manner, and, in the case of 3, also with stereocontrol.