Trifluoromethyl Group (CF3) Induced Regioselective Larock Indole Synthesis from Unsymmetric β-CF3-1,3-enynes

IF 4.9 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2025-03-24 DOI:10.1021/acs.orglett.5c00501

Yan-Hua Qiu, Pei-Yan Ma, Wen-Hao Shao, Chang-Qi Huang, Yongshun Wen, Zi-Ying Huang, Wenjun Luo, Lipeng Long, Xiangjun Peng, Daohong Yu

引用次数: 0

Abstract

The indole skeleton exists widely in natural products, pharmaceuticals, and materials. We disclose here a trifluoromethyl group induced regioselective Larock indole synthetic method from unsymmetric 2-CF₃-1,3-enynes. The presence of a trifluoromethyl group is determinable for the regioselectivity. Once the CF₃ group was replaced with the methyl or phenyl group, a ratio of 1:1 to 1:1.4 isomers were obtained. This strategy features good regioselectivity, broad substrate scope, and high functional group tolerance. The protocol reported here offers an alternative solution to the rare 3,4-functionalization of 2-CF₃-1,3-enynes. The products were further transformed to show distinctive reactivity in hydroboration–oxidation and hydro-bromination.

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三氟甲基（CF3）诱导非对称β-CF3-1,3-炔合成Larock吲哚

吲哚骨架广泛存在于天然产物、药品和材料中。本文提出了一种由不对称2-CF3-1,3-炔基三氟甲基诱导的区域选择性Larock吲哚合成方法。三氟甲基的存在对区域选择性是可确定的。一旦CF3基团被甲基或苯基取代，得到的同分异构体的比例为1:1和1:1.4。该策略具有良好的区域选择性、广泛的底物范围和高官能团耐受性。本文报道的方案为2- cf3 -1,3-炔罕见的3,4功能化提供了另一种解决方案。产物经进一步转化，在硼氢化氧化和溴氢化反应中表现出独特的反应活性。

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 Letters 化学-有机化学

CiteScore

9.30

自引率

11.50%

发文量

1607

审稿时长

1.5 months

期刊介绍： Organic Letters invites original reports of fundamental research in all branches of the theory and practice of organic, physical organic, organometallic,medicinal, and bioorganic chemistry. Organic Letters provides rapid disclosure of the key elements of significant studies that are of interest to a large portion of the organic community. In selecting manuscripts for publication, the Editors place emphasis on the originality, quality and wide interest of the work. Authors should provide enough background information to place the new disclosure in context and to justify the rapid publication format. Back-to-back Letters will be considered. Full details should be reserved for an Article, which should appear in due course.