Tf2O-Induced Selective 1,3-Transposition/Cyclization of Ynones in DMF

IF 4.6 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Chemistry Frontiers Pub Date : 2024-12-14 DOI:10.1039/d4qo01890g

Huilin Lan, Wenting Liu, Wen Liu, Jiajian Peng, Ying Bai, Xinxin Shao

引用次数: 0

Abstract

A chemo and regio-selective system for activating C=O and S=O bonds under transition metal-free conditions is described. Thus, a Tf2O-mediated 1,3-transposition of ynones in DMF has been developed, providing a versatile pathway for the downstream synthesis of diverse five- and seven-membered heterocycles. Furthermore, the catalytic migration of carbonyl functionality conjugated to an alkyne unit is investigated. In the presence of sulfoxide, which undergoes a Pummerer reaction, the in-situ generation of highly reactive sulfonium salts enables efficient access to a wide range of sulfur-containing annulated scaffolds. Importantly, 3-SCF2D chromones were obtained in high yields and D-incorporation. This divergent methodology offers a versatile platform for maximizing molecular complexity and diversity.

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介绍了一种在无过渡金属条件下活化 C=O 和 S=O 键的化学和区域选择性系统。因此，开发出了一种 Tf2O 介导的 1,3-炔酮在 DMF 中的反式合成方法，为下游合成各种五元和七元杂环提供了多用途途径。此外，还研究了与炔单元共轭的羰基官能团的催化迁移。在发生 Pummerer 反应的亚砜存在下，原位生成的高活性锍盐能够有效地获得各种含硫环状支架。重要的是，3-SCF2D 色酮可以高产率和 D-incorporation方式获得。这种不同的方法为最大限度地提高分子的复杂性和多样性提供了一个多功能平台。

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.