Relay Catalysis of Bismuth Trichloride and Byproduct Hydrogen Bromide Enables the Synthesis of Carbazole and Benzo[α]carbazoles from Indoles and α‐Bromoacetaldehyde Acetals,Advanced Synthesis & Catalysis

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Relay Catalysis of Bismuth Trichloride and Byproduct Hydrogen Bromide Enables the Synthesis of Carbazole and Benzo[α]carbazoles from Indoles and α‐Bromoacetaldehyde Acetals
Advanced Synthesis & Catalysis ( IF 4.4 ) Pub Date : 2018-07-09 , DOI: 10.1002/adsc.201800669
Fengtian Wu ₁ , Wenbo Huang ₁ , Yiliqi ₁ , Jian Yang ₁ , Yanlong Gu _{1,

2}

Affiliation

Benzo[α]carbazoles were synthesized from 2‐phenylindoles and α‐bromoacetaldehyde using bismuth trichloride as a catalyst. The reaction was triggered by a bismuth trichloride‐catalyzed Friedel‐Crafts alkylation of these two precursors, which provided a tryptaldehyde intermediate that underwent intramolecular olefination to form the final product. Interestingly, the HBr byproduct generated in the upstream step of the reaction catalyzed the following downstream reaction steps, thus creating a byproduct‐participated relay catalytic process. Motivated by this mechanism, we developed a three‐component reaction of indole, α‐bromoacetaldehyde acetal, and 1,3‐dicarbonyl compounds. This study offers a straightforward method for synthesizing substituted carbazoles.

中文翻译：

三氯化铋和副产物溴化氢的中继催化使吲哚和α-溴乙醛缩醛合成咔唑和苯并[α]咔唑成为可能

以三氯化铋为催化剂，由2-苯基吲哚和α-溴乙醛合成苯并[α]咔唑。该反应是由这两种前体的三氯化铋催化的Friedel-Crafts烷基化反应引发的，该反应提供了一种经过分子内烯化反应形成最终产物的三聚甲醛中间体。有趣的是，在反应的上游步骤中产生的HBr副产物催化了随后的下游反应步骤，从而形成了一种由副产物参与的中继催化过程。在这种机理的推动下，我们开发了吲哚，α-溴乙醛缩醛和1,3-二羰基化合物的三组分反应。这项研究提供了一种直接的方法来合成取代的咔唑。

更新日期：2018-07-09

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