101261-98-7Relevant academic research and scientific papers
Nickel-catalyzed guerbet type reaction: C-alkylation of secondary alcohols via double (de)hydrogenation
Babu, Reshma,Subaramanian, Murugan,Midya, Siba P.,Balaraman, Ekambaram
, p. 3320 - 3325 (2021)
Acceptorless double dehydrogenative cross-coupling of secondary and primary alcohols under nickel catalysis is reported. This Guerbet type reaction provides an atom- and a step-economical method for the C-alkylation of secondary alcohols under mild, benign conditions. A broad range of substrates including aromatic, cyclic, acyclic, and aliphatic alcohols was well tolerated. Interestingly, the C-alkylation of cholesterol derivatives and the double C-alkylation of cyclopentanol with various alcohols were also demonstrated.
Aldehyde-catalyzed transition metal-free dehydrative β-alkylation of methyl carbinols with alcohols
Xu, Qing,Chen, Jianhui,Liu, Quan
supporting information, p. 697 - 704 (2013/04/10)
Different to the borrowing hydrogen strategy in which alcohols were activated by transition metal-catalyzed anaerobic dehydrogenation, the direct addition of aldehydes was found to be an effective but simpler way of alcohol activation that can lead to efficient and green aldehyde-catalyzed transition metal-free dehydrative C-alkylation of methyl carbinols with alcohols. Mechanistic studies revealed that the reaction proceeds via in situ formation of ketones by Oppenauer oxidation of the methyl carbinols by external aldehydes, aldol condensation, and Meerwein-Ponndorf-Verley (MPV)-type reduction of α,β-unsatutated ketones by substrate alcohols, affording the useful long chain alcohols and generating aldehydes and ketones as the by-products that will be recovered in the next condensation to finish the catalytic cycle. Copyright
