Photocatalyzed Sulfoximination/Amidation of (Het)Arylethenes Tethered N-Tosyl Amide: A Versatile Entry to Sulfoximidoyl β- and γ-Lactams

IF 4.6 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Chemistry Frontiers Pub Date : 2024-06-18 DOI:10.1039/d4qo00631c

Weilong Lin, Chengtan Li, Yuming Yang, Xiaolan Zheng, Cairong Zhang, Hui Cai

引用次数: 0

Abstract

The lactam and sulfoximine motifs are common in natural and biologically active molecules, and alkenes are important building blocks in synthetic chemistry. Through photoredox-mediated formation cation intermediates, we have developed a highly versatile method for the preparation of various sulfoximidoyl lactams via C-N bond formation between C=C and amide motifs. The mild reaction conditions, broad functional group tolerance and excellent trans-selectivity would make it a general and efficient approach towards such novel analogues containing both valuable sulfoximine and lactam motifs for possible therapeutic use.

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光催化(Het)芳香族系链 N-对甲基苯磺酰酰胺的氧化硫/酰胺化作用：硫代亚氨酰 β- 和 γ-内酰胺的多功能途径

内酰胺和亚磺酰亚胺基团在天然和生物活性分子中很常见，而烯是合成化学中的重要构件。通过光氧化介导的阳离子中间体的形成，我们开发了一种通过 C=C 和酰胺基团之间的 C-N 键形成制备各种亚磺酰亚胺内酰胺的多功能方法。该方法反应条件温和，对官能团具有广泛的耐受性和出色的反向选择性，因此是一种通用而高效的方法，可用于制备同时含有有价值的亚磺酰亚胺和内酰胺基团的新型类似物，并可能用于治疗。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

Organic Chemistry Frontiers CHEMISTRY, ORGANIC-

CiteScore

7.90

自引率

11.10%

发文量

686

审稿时长

1 months

期刊介绍： Organic Chemistry Frontiers is an esteemed journal that publishes high-quality research across the field of organic chemistry. It places a significant emphasis on studies that contribute substantially to the field by introducing new or significantly improved protocols and methodologies. The journal covers a wide array of topics which include, but are not limited to, organic synthesis, the development of synthetic methodologies, catalysis, natural products, functional organic materials, supramolecular and macromolecular chemistry, as well as physical and computational organic chemistry.