Brønsted Acid-Catalyzed Solvent-Controlled Regioselective Thiolation of 2-Furylcarbinols

IF 4.6 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Chemistry Frontiers Pub Date : 2024-11-20 DOI:10.1039/d4qo01904k

Chunyu Zhang, Tianyu Lin, Qing Liu, Rui Hu, Weidong Rao

引用次数: 0

Abstract

A novel p-toluenesulfonic acid-catalyzed solvent-controlled regioselective thiolation of 2-furylcarbinols for the efficient and chemoselective preparation of densely functionalized furan- and lactone-based sulfides under mild metal-free conditions has been developed. By using thiols as nucleophiles in DCE at 80 °C, a new reactivity involving a cascade C5-selective nucleophilic substitution/protonation-hydration/C-S bond cleavage/thia-Michael addition leads to lactone-based sulfides rather than the known Piancatelli-type rearrangement products was revealed for the first time. This tunable thiolation protocol enables ready access to both furan- and lactone-based sulfide derivatives with excellent yields by the judicious choice of the reaction solvent.

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布氏酸催化的溶剂控制型 2-呋喃基甲醇区域选择性硫代反应

本研究开发了一种新型对甲苯磺酸催化溶剂控制的 2-呋喃甲醇区域选择性硫代反应，用于在温和的无金属条件下高效、化学选择性地制备致密官能化的呋喃基和内酯基硫化物。通过在 80 °C 的二氯乙烷中使用硫醇作为亲核剂，首次发现了一种新的反应性，其中涉及级联 C5 选择性亲核取代/质子化-水合/C-S 键裂解/噻-迈克尔加成，从而生成内酯基硫化物，而不是已知的 Piancatelli 型重排产物。通过对反应溶剂的明智选择，这种可调硫醇化方案可随时获得呋喃基和内酯基硫化物衍生物，并具有极佳的产率。

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.