Selective Synthesis of Benzo[a]Carbazoles and Indolo[2,1‐a]‐Isoquinolines via Rh(III)‐Catalyzed C−H Functionalizations of 2‐Arylindoles with Sulfoxonium Ylides,Advanced Synthesis & Catalysis

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Selective Synthesis of Benzo[a]Carbazoles and Indolo[2,1‐a]‐Isoquinolines via Rh(III)‐Catalyzed C−H Functionalizations of 2‐Arylindoles with Sulfoxonium Ylides
Advanced Synthesis & Catalysis ( IF 4.4 ) Pub Date : 2018-08-02 , DOI: 10.1002/adsc.201800622
Guang Chen ₁ , Xinying Zhang ₁ , Ruixue Jia ₁ , Bin Li ₁ , Xuesen Fan ₁

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A highly chem‐ and regioselective synthesis of diversely substituted benzo[a]carbazoles and indolo[2,1‐a]‐isoquinolines through Rh(III)‐catalyzed cascade reactions of 2‐arylindoles with sulfoxonium ylides is presented. To be specific, treatment of 2‐arylindoles, 2‐arylindole‐3‐carbaldehydes, 2‐arylindole‐3‐carbonitriles or 2‐aryl‐3‐methylindoles with sulfoxonium ylides under the catalysis of Rh(III) led to the selective formation of 6‐aryl/alkyl benzo[a]carbazoles, 5‐acylbenzo[a]carbazoles, 6‐amino‐5‐acylbenzo[a]carbazoles or 12‐methylindolo[2,1‐a]isoquinolines, respectively. Mechanistically, the formation of the title compounds involves a cascade process including metalation of the inert C(sp²)−H bond, migratory insertion of ylide into the carbon‐metal bond via an in situ carbenoid formation, protodemetalation, and condensation. To our knowledge, this is the first example in which β‐carbonyl sulfoxonium ylides were used as stable carbene precursors and bifunctional C2 synthons to afford benzo[a]carbazoles and indolo[2,1‐a]isoquinolines.

中文翻译：

通过Rh（III）催化2-Arylindoles的Soxoxonium内鎓盐的C-H官能团选择性合成苯并[a]咔唑和吲哚[2,1-a]-异喹啉

提出了通过Rh（III）催化2-芳基吲哚与sulf基ox的级联反应，对不同取代的苯并[ a ]咔唑和吲哚并[ 2,1- a ]-异喹啉进行高度化学和区域选择性的合成。具体而言，在Rh（III）的催化下，用亚砜亚砜处理2-芳基吲哚，2-芳基吲哚-3-甲醛，2-芳基吲哚-3-腈或2-芳基-3-甲基吲哚导致选择性地形成6 -芳基/烷基苯并[一个]咔唑，5- acylbenzo [一个]咔唑，6-氨基-5- acylbenzo [一个]咔唑或12 methylindolo [2,1-一个分别是]异喹啉。从机理上讲，标题化合物的形成涉及级联过程，包括惰性C（sp ²）-H键的金属化，通过原位类胡萝卜素的形成将叶立德迁移插入碳-金属键，原金属脱金属和缩合。据我们所知，这是第一个将β-羰基sulf代亚砜用作稳定的卡宾前体和双官能C2合成子以提供苯并[ a ]咔唑和吲哚[2,1- a ]异喹啉的实例。

更新日期：2018-08-02

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