Categories: C-C Bond Formation > Oxygen-containing molecules > Carbonyl compounds >
Synthesis of substituted carbonyl compounds by 1,5-Additions
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Recent Literature
A nickel-catalyzed reductive cross-coupling reaction of aryl cyclopropyl
ketones with easily accessible unactivated alkyl bromides provides
γ-alkyl-substituted ketones. Initial mechanistic studies revealed that the
reaction proceeds via radical cleavage of the alkyl bromide.
N. Cui, T. Lin, Y.-E. Wang, J. Wu, Y. Han, X. Xu, F. Xue, D. Xiong, P. J.
Walsh, J. Mao, Org. Lett.,
2022, 24, 3987-3992.
A highly efficient Pd-catalyzed arylative ring expansion of cyclobutanols with
aryl chlorides via C-C bond cleavage at low catalyst loadings tolerates a wide
range of functional groups and substitution patterns, thus constituting a
straightforward alternative for preparing rather elusive γ-arylated ketones.
A. Ziadi, R. Martin, Org. Lett., 2012,
14, 1266-1269.
An efficient Na2S2O8-promoted radical coupling
of tertiary cycloalkanols with alkynyl hypervalent iodide reagents provides β-,
γ- and δ-alkynylated ketones via C-C bond cleavage. This tandem ring-opening/alkynylation
procedure offers mild conditions and wide substrate scope.
S. Wang, L.-N. Guo, H. Wang, X.-H. Duan, Org. Lett.,
2015,
17, 4798-4801.