期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 85, 期 8, 页码 5475-5485出版社
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.0c00227
关键词
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资金
- Rutgers University
- NSF (CAREER) [CHE-1650766]
- NSF-MRI grant [CHE-1229030]
- Wroclaw Center for Networking and Supercomputing [WCSS159]
- NSF [CHE-1915878]
N-Acyl-glutarimides have emerged as the most reactive precursors for N-C(O) bond cross-coupling reactions to date, wherein the reactivity is driven by ground-state destabilization of the amide bond. Herein, we report a full study on the effect of a glutarimide ring on the structures, electronic properties, and reactivity of fully perpendicular N-acyl-glutarimide amides. Most notably, this report demonstrates the generality of deploying N-acyl-glutarimides to achieve full twist of the acyclic amide bond, and results in the discovery of N-acyl-glutarimide amide with an almost perfect twist value, t = 89.1 degrees. X-ray structures of five new N-acyl-glutarimides are reported. Reactivity studies in the Suzuki-Miyaura cross-coupling and transamidation reactions provide insight into the reactivity of N-acyl-glutarimides in metal-catalyzed and transition-metal-free reactions. The effect of distortion, structures, and rotational barriers around the N-C(O) axis is discussed. The ability to achieve full distortion of the amide bond significantly expands the range of reagents available for N-C(O) cross-coupling reactions.
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