Nitrene C−H Bond Insertion Approach to Carbazolones and Indolones, and a Reactivity Departure for 7-Membered Analogues**,Chemistry - A European Journal

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Nitrene C−H Bond Insertion Approach to Carbazolones and Indolones, and a Reactivity Departure for 7-Membered Analogues**
Chemistry - A European Journal ( IF 3.9 ) Pub Date : 2023-09-26 , DOI: 10.1002/chem.202302995
Mahesh K Lakshman _{1,

2} , Dellamol Sebastian _{1,

2} , Padmanava Pradhan ₁ , Michelle C Neary ₃ , Alexis M Piette ₄ , Samuel P Trzebiatowski ₄ , Alexander E K Henriques ₄ , Patrick H Willoughby ₄

Affiliation

2-Arylcyclohexane-1,3-diones and 2-arylcyclopentane-1,3-diones can be converted in a facile 2-step, 1-pot manner to 2-aryl-3-azidocycloalk-2-en-1-ones. These azides can be smoothly cyclized to carbazolones and indolones with catalytic Rh₂(O₂CC₇H₁₅)₄. Although 3-azido-2-phenylcyclohept-2-en-1-one could be readily prepared from 2-phenylcycloheptane-1,3-dione, by contrast the Rh-catalyzed cyclization gave an azirine in preference to the indole. Mechanistic and DFT studies complement the synthetic work.

中文翻译：

咔唑酮和吲哚酮的氮烯 C−H 键插入方法以及 7 元类似物的反应性偏离**

2-芳基环己烷-1,3-二酮和2-芳基环戊烷-1,3-二酮可以通过简单的两步、一锅法转化为2-芳基-3-叠氮基环烷-2-en-1-酮。这些叠氮化物可以在催化Rh ₂ (O ₂ CC ₇ H ₁₅ ) ₄的作用下顺利环化为咔唑酮和吲哚酮。虽然 3-叠氮基-2-苯基环庚-2-en-1-酮可以很容易地从 2-苯基环庚烷-1,3-二酮制备，但相比之下，Rh 催化的环化反应优先于吲哚生成氮丙啶。机理和 DFT 研究补充了综合工作。

更新日期：2023-09-26

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