Br-2-Catalyzed regioselective dehydrative coupling of indoles with acyloins: direct synthesis of alpha-(3-indolyl) ketones

Liang Deqiang; Li Xiangguang; Li Yanni; Yang Yungang; Gao Shulin; Cheng Ping

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Br-2-Catalyzed regioselective dehydrative coupling of indoles with acyloins: direct synthesis of alpha-(3-indolyl) ketones

机译：BR-2催化的吲哚与酰基吲哚的区域选择性脱水偶联：直接合成α-（3-吲哚基）酮

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An efficient Br-2-catalyzed synthesis of alpha-(3-indolyl) ketones via dehydrative coupling of simple indoles with acyloins is presented. This reaction proceeded with high C-3 selectivity and a wide substrate scope, and without any metal catalyst. Both the activation of alcohols by carbonyl groups and the catalysis of Br-2 were essential. Density functional theory (DFT) calculations indicated that carbonyl groups not only enhanced the electrophilicities of the resulting carbocations, but acted as stabilizers for them as well, and that the activation of the catalyst by hydrogen bonding between Br-2 and the hydroxyl hydrogen of acyloins was the key process for this transformation.

机译：提出了通过脱水吲哚与酰胺的脱水偶联的高效α-（3-吲哚基）酮的合成α-（3-吲哚基）酮的合成。该反应采用高C-3选择性和宽基板范围，无需任何金属催化剂进行。通过羰基的醇激活和BR-2的催化是必需的。密度泛函理论（DFT）计算表明，羰基不仅增强了所得碳酸的电泳，而且还具有作为它们的稳定剂，并且通过Br-2与酰基羟基氢氢键合的氢键活化是这种转变的关键过程。

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《RSC Advances》 |2016年第35期|共6页
作者
Liang Deqiang; Li Xiangguang; Li Yanni; Yang Yungang; Gao Shulin; Cheng Ping;
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Kunming Univ Dept Chem Kunming 650214 Peoples R China;

Kunming Univ Dept Chem Kunming 650214 Peoples R China;

Kunming Univ Dept Chem Kunming 650214 Peoples R China;

Kunming Univ Dept Chem Kunming 650214 Peoples R China;

Kunming Univ Dept Chem Kunming 650214 Peoples R China;

Shanghai Univ Sch Environm &

Chem Engn Shanghai 200444 Peoples R China;

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正文语种 eng
中图分类化学;
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1. Br-2-Catalyzed regioselective dehydrative coupling of indoles with acyloins: direct synthesis of alpha-(3-indolyl) ketones [J] . Liang Deqiang, Li Xiangguang, Li Yanni, RSC Advances . 2016,第35期

机译：BR-2催化的吲哚与酰基吲哚的区域选择性脱水偶联：直接合成α-（3-吲哚基）酮
2. Direct Regioselective Oxidative Cross-Coupling of Indoles with Methyl Ketones: A Novel Route to C3-Dicarbonylation of Indoles [J] . Gao Qinghe, Zhang Jingjing, Wu Xia, Organic letters . 2015,第1期

机译：吲哚与甲基酮的直接区域选择性氧化交叉偶联：吲哚C3-二羰基化的新途径。
3. Intramolecular dehydrative coupling of tertiary amines and ketones promoted by KO-t-Bu/DMF: A new synthesis of indole derivatives [J] . Wei W.-T., Dong X.-J., Nie S.-Z., Organic letters . 2013,第23期

机译：KO-t-Bu / DMF促进叔胺和酮的分子内脱水偶联：吲哚衍生物的新合成
4. Synthesis of novel tetracyclic indolines using electrophilic indoles and 2-aminophenyl α,β-unsturated ketones [C] . Takuya Shimada, Takayoshi Arai 日本化学会春季年会講演予稿集 . 2018

机译：使用电泳吲哚和2-氨基苯基α，β-不尿液酮的新型四环吲哚吲哚
5. Recent advances in indole aryne cycloaddition chemistry. Part I: Total synthesis of (+/-)-cis-trikentrin B. Part II: Investigation into the regioselectivity of 6,7-indole aryne cycloadditions. Part III: Synthesis and reactions of novel tribromoindoles. [D] . Nerurkar, Alok. 2015

机译：吲哚芳烃环加成化学的最新进展。第一部分：（+/-）-顺式trikentrin B的全合成。第二部分：6,7-吲哚亚芳基环加成反应的区域选择性研究。第三部分：新型三溴吲哚的合成与反应。
6. Catalytic Synthesis of Substituted Indoles and Quinolines from the Dehydrative C–H Coupling of Arylamines with 12- and 13-Diols [O] . Hanbin Lee, Chae S. Yi -1

机译：芳胺与12-和13-二元醇脱水CH偶联反应催化合成取代的吲哚和喹啉
7. Total Synthesis of (+)-Gliocladin C Based on One-Pot Construction of a 3a-(3-Indolyl)pyrroloindoline Skeleton by Sulfonium-Mediated Cross-Coupling of Tryptophan and Indole [O] . -1

机译：基于三盆地结构的3A-（3-吲哚基）吡咯啉骨架的单盆结构通过色氨酸和Indole的交叉偶联的单盆性施工总结（+） - Gliocladin C.

Br-2-Catalyzed regioselective dehydrative coupling of indoles with acyloins: direct synthesis of alpha-(3-indolyl) ketones

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