Langlois试剂光诱导区域和立体选择性氢化三氟甲基化的研究。

IF 3.3 2区化学 Q1 CHEMISTRY, ORGANIC

Journal of Organic Chemistry Pub Date : 2025-05-13 DOI:10.1021/acs.joc.5c00193

Tian Li,Miao Liu,Zhao-Xiang Luo,Xian-Jin Qin,Xin-Shan Ye,De-Cai Xiong

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引用次数: 0

摘要

氟化已证明有可能改善碳水化合物的物理化学和酶性质。氢三氟甲基化是引入三氟甲基的新兴反应。然而，由于缺乏区域选择性和立体选择性，糖基的氢三氟甲基化一直具有挑战性。在此，我们描述了一种高效、高选择性和广泛适用的光诱导三氟甲基化策略，使用成本效益高的三氟甲烷磺酸钠得到1,2-二脱氧-2-三氟甲基糖。

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Photoinduced Regio- and Stereoselective Hydrotrifluoromethylation of Glycals with Langlois Reagent.

Fluorination has demonstrated the potential to improve the physicochemical and enzymatic properties of carbohydrates. Hydrotrifluoromethylation is an emerging reaction to introduce trifluoromethyl groups. However, the hydrotrifluoromethylation of glycals has been challenging because of the lack of regioselectivity and stereoselectivity. Herein, we describe an efficient, highly selective, and broadly applicable photoinduced hydrotrifluoromethylation strategy of glycals using cost-effective sodium trifluoromethanesulfonate to give 1,2-dideoxy-2-trifluoromethyl sugars.

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来源期刊

Journal of Organic Chemistry 化学-有机化学

CiteScore

6.20

自引率

11.10%

发文量

1467

审稿时长

2 months

期刊介绍： Journal of Organic Chemistry welcomes original contributions of fundamental research in all branches of the theory and practice of organic chemistry. In selecting manuscripts for publication, the editors place emphasis on the quality and novelty of the work, as well as the breadth of interest to the organic chemistry community.