Tuning Triplet Energy Transfer of Hydroxamates as the Nitrene Precursor for Intramolecular C(sp3)–H Amidation,Journal of the American Chemical Society

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Tuning Triplet Energy Transfer of Hydroxamates as the Nitrene Precursor for Intramolecular C(sp3)–H Amidation
Journal of the American Chemical Society ( IF 14.4 ) Pub Date : 2020-03-04 , DOI: 10.1021/jacs.0c00868
Hoimin Jung _{1,

2} , Hyeyun Keum _{1,

2} , Jeonguk Kweon _{1,

2} , Sukbok Chang _{1,

2}

Affiliation

Reported herein is the design of a photosensitization strategy to generate triplet nitrenes and its applicability for the intramolecular C-H amidation reactions. Substrate optimization by tuning physical organic parameters according to the proposed energy transfer pathway led us to identify hydroxamates as a convenient nitrene precursor. While more classical nitrene sources, representatively organic azides, were ineffective under the current photosensitization conditions, hydroxamates which are readily available from alcohols or carboxylic acids are highly efficient in accessing synthetically valuable 2-oxazolidinones and γ-lactams by visible light. Mechanism studies supported our working hypothesis that the energy transfer path is mainly operative.

中文翻译：

调节异羟肟酸酯作为分子内 C(sp3)-H 酰胺化的氮烯前体的三重态能量转移

本文报道了产生三线态氮烯的光敏化策略的设计及其在分子内 CH 酰胺化反应中的适用性。通过根据提议的能量转移途径调整物理有机参数来优化基材，使我们将异羟肟酸盐鉴定为一种方便的氮烯前体。虽然更经典的氮烯来源，以有机叠氮化物为代表，在当前的光敏化条件下无效，但容易从醇或羧酸中获得的异羟肟酸酯在通过可见光获取具有合成价值的 2-恶唑烷酮和 γ-内酰胺方面非常有效。机理研究支持了我们的工作假设，即能量转移路径主要是有效的。

更新日期：2020-03-04

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