874009-12-8Relevant academic research and scientific papers
Hydrogen borrowing catalysis using 1° and 2° alcohols: Investigation and scope leading to α and β branched products
Frost, James R.,Cheong, Choon Boon,Akhtar, Wasim M.,Caputo, Dimitri F.J.,Christensen, Kirsten E.,Stevenson, Neil G.,Donohoe, Timothy J.
supporting information, (2021/04/07)
The alkylation of a variety of ketones using 1° or 2° alcohols under hydrogen borrowing catalysis is described. Initial research focused on the α-alkylation of cyclopropyl ketones with higher 1° alcohols (i.e. larger than MeOH), leading to the formation of α-branched products. Our search for additional substrates with which to explore this chemistry led us to discover that di-ortho-substituted aryl ketones were also privileged scaffolds, with Ph? (C6Me5) ketones being the optimal choice. Further investigations revealed that this motif was crucial for alkylation with 2° alcohols forming β-branched products, which also provided an opportunity to study diastereoselective and intramolecular hydrogen borrowing processes.
Synergistic Photoredox/Nickel Coupling of Acyl Chlorides with Secondary Alkyltrifluoroborates: Dialkyl Ketone Synthesis
Amani, Javad,Molander, Gary A.
, p. 1856 - 1863 (2017/02/10)
Visible light photoredox/nickel dual catalysis has been employed in the cross-coupling of acyl chlorides with potassium alkyltrifluoroborates. This protocol, based on single-electron-mediated alkyl transfer, circumvents the restriction of using reactive alkylmetallic nucleophiles in transition-metal-catalyzed acylation and achieves a mild and efficient method for the synthesis of unsymmetrical alkyl ketones. In this approach, a variety of acyl chlorides have been successfully coupled with structurally diverse potassium alkyltrifluoroborates, generating the corresponding ketones with good yields.
