Enantioselective Transformation of Hydrazones via Remote NHC Catalysis: Activation Across C═N and N–N Bonds

IF 11.3 1区化学 Q1 CHEMISTRY, PHYSICAL

ACS Catalysis Pub Date : 2024-11-30 DOI:10.1021/acscatal.4c06029

Jiamiao Jin, Ya Lv, Wenli Tang, Kunpeng Teng, Yixian Huang, Jingxin Ding, Tingting Li, Guanjie Wang, Yonggui Robin Chi

引用次数: 0

Abstract

The catalytic asymmetric transformation of nitrogen atoms to prepare heterocyclic molecules is of significant value in organic synthesis and biological applications. Here, we disclose the activation of the nitrogen atom in hydrazine-derived hydrazone via an N-heterocyclic carbene (NHC) organic catalyst for highly enantioselective formal cycloaddition reactions. The range of NHC catalysis extends across several (carbon and hetero) atoms and diverse chemical bonds (C═N and N–N bonds) to activate nitrogen atoms at remote sites with excellent reactivity and (stereo)selectivity control. Our strategy for nitrogen atom activation, along with the NHC-bound diaza-diene intermediate generated during the catalytic process, offers alternative solutions for organic synthesis.

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来源期刊

ACS Catalysis CHEMISTRY, PHYSICAL-

CiteScore

20.80

自引率

6.20%

发文量

1253

审稿时长

1.5 months

期刊介绍： ACS Catalysis is an esteemed journal that publishes original research in the fields of heterogeneous catalysis, molecular catalysis, and biocatalysis. It offers broad coverage across diverse areas such as life sciences, organometallics and synthesis, photochemistry and electrochemistry, drug discovery and synthesis, materials science, environmental protection, polymer discovery and synthesis, and energy and fuels. The scope of the journal is to showcase innovative work in various aspects of catalysis. This includes new reactions and novel synthetic approaches utilizing known catalysts, the discovery or modification of new catalysts, elucidation of catalytic mechanisms through cutting-edge investigations, practical enhancements of existing processes, as well as conceptual advances in the field. Contributions to ACS Catalysis can encompass both experimental and theoretical research focused on catalytic molecules, macromolecules, and materials that exhibit catalytic turnover.