Catalytic radical-based domino reactions represent important advances in synthetic organic chemistry. Their development benefits synthesis by providing atom- and step-economical methods to complex molecules. Intricate combinations of radical, cationic, anionic, oxidative/reductive, and transition metal mechanistic steps result in cyclizations, additions, fragmentations, ring-expansions, and rearrangements. This Perspective summarizes recent developments in the field of catalytic domino processes.
Visible light-mediated photoredox catalysis enables the chemoselective reduction of activated carbonheteroatom bonds as a function of reduction potential. The expansion of the scope of C-X bond reductions towards less activated motifs, such as ethers, amines and sulfides, is important to both organic synthesis and macromolecular degradation method development. In the present report, exploration of photoredox catalysis in alcoholic solvents mediated a decrease in the super-stoichiometric use of i Pr 2 NEt and HCO 2 H in the reduction of α-keto ethers, amines and sulfides. Additionally, in the absence of fragmentation, CC bond formation was afforded, suggesting an intermediate ketyl radicals are present in these transformations. * Yields isolated for substrates 8, 9, 10 were isolated in 85-90% yield when reacted under the first generation conditions (see Fig 1 (A)).
A convergent and scalable synthesis of the archazolid western hemisphere has been completed. The V-ATPase inhibitory activity of this compound along with a previously prepared eastern domain was then tested using a convenient Arabidopsis-based V-ATPase assay.
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