1403266-85-2Relevant academic research and scientific papers
Cu-Catalyzed Hydroxymethylation of Unactivated Alkyl Iodides with CO To Provide One-Carbon-Extended Alcohols
Zhao, Siling,Mankad, Neal P.
, p. 5867 - 5870 (2018)
We have developed a reductive carbonylation method by which unactivated alkyl iodides can be hydroxymethylated to provide one-carbon-extended alcohol products under Cu-catalyzed conditions. The method is tolerant of alkyl β-hydrogen atoms, is robust towards a wide variety of functional groups, and was applied to primary, secondary, and tertiary alkyl iodide substrates. Mechanistic experiments indicate that the transformation proceeds by atom-transfer carbonylation (ATC) of the alkyl iodide followed in tandem by two CuH-mediated reductions in rapid succession. This radical mechanism renders the Cu-catalyzed system complementary to precious-metal-catalyzed reductive carbonylation reactions.
Copper-Catalyzed Alkoxycarbonylation of Alkyl Iodides for the Synthesis of Aliphatic Esters: Hydrogen Makes the Difference
Geng, Hui-Qing,Wu, Xiao-Feng
, p. 8062 - 8066 (2021/10/25)
A copper-catalyzed alkoxycarbonylation transformation of unactivated alkyl iodides has been developed. Various alkyl iodides can be converted into the corresponding tert-butyl esters in good yields. NaOtBu acts as both a nucleophile and a base. Moreover, other types of aliphatic esters can also be obtained in moderated yields if extra alcohols are added. Both primary and secondary alkyl alcohols can react successfully.
Copper-catalyzed reduction of alkyl triflates and iodides: An efficient method for the deoxygenation of primary and secondary alcohols
Dang, Hester,Cox, Nick,Lalic, Gojko
supporting information, p. 752 - 756 (2014/01/23)
We describe an effective method for catalytic reduction of 1°alkyl sulfonates, and 1°and 2°iodides in the presence of a wide range of functional groups. This Cu-catalyzed reaction provides a means for the effective deoxygenation of alcohols, as demonstrated by the highly selective reduction of 1°alcohols using a triflation/reduction sequence. A preliminary study of the reaction mechanism suggests that the reduction does not involve free-radical intermediates. Primarily reduced: The copper-catalyzed reduction of 1°alkyl sulfonates, and 1°and 2°iodides, which is effective in the presence of a wide range of functional groups, provides a means for the effective deoxygenation of alcohols. A preliminary study of the reaction mechanism suggests that the reduction does not involve free-radical intermediates. Copyright
