Synthesis of substituted carbonyl compounds by 1,5-Additions
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.