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DOI: 10.1055/s-0039-1690048
Highly Efficient Synthesis of Hindered 3-Azoindoles via Metal-Free C–H Functionalization of Indoles
This work was carried out within ANR JCJC grant ‘2al-Vis-Phot-CH’ (ANR-15-CE29-0004-01).Publikationsverlauf
Received: 20. November 2019
Accepted after revision: 06. Januar 2020
Publikationsdatum:
16. Januar 2020 (online)
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Published as part of the Bürgenstock Special Section 2019 Future Stars in Organic Chemistry
Abstract
Although 3-azoindoles have recently emerged as an appealing family of photoswitch molecules, the synthesis of such compounds has been poorly covered in the literature. Herein a high-yielding and operationally simple protocol is reported allowing the synthesis of 3-azoindoles, featuring important steric hindrance around the azo motif. Remarkably, this C–H coupling is characterized by excellent atom economy and occurs under metal-free conditions, at room temperature, and within few minutes, delivering the expected products in excellent yields (quantitatively in most of the cases). Accordingly, a library of new molecules, with potential applications as photochromic compounds, is prepared.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0039-1690048.
- Supporting Information
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