Selective Dehydrogenative Acylation of Enamides with Aldehydes Leading to Valuable β‑Ketoenamides

Rui-Hua Liu^a, Zhen-Yao Shen^a, Cong Wang^a, Teck-Peng Loh^a,b, and Xu-Hong Hu^a,*

^aInstitute of Advanced Synthesis, School of Chemistry and Molecular Engineering, Nanjing Tech University, Nanjing 211816, China

^bDivision of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore 637371, Singapore

Abstract:We have presented a unique example of dehydrogenativeacylation of enamides with aldehydes enabled by an earthabundantiron catalyst. The protocol provides the straightforward access to valuable β-ketoenamides with ample substrate scope and excellent functional group tolerance. Notably, distinct C−H acylation of enamide rather than at N−H moiety site occurs with absolute Z-selectivity was observed. Late-stage modifications of complex molecules and versatile synthetic utility of β-ketoenamides further highlight the practicability of this transformation.

Org. Lett.2020,22, 944-949.(2019年影响因子：6.091)

Organic Chemistry Portal亮点报道：https://www.organic-chemistry.org/abstracts/lit7/205.shtm

论文链接：https://pubs.acs.org/doi/10.1021/acs.orglett.9b04495