Issue 31, 2023

Macrocyclization via remote meta-selective C–H olefination using a practical indolyl template

Abstract

The synthesis of macrocyclic compounds with different sizes and linkages remains a great challenge via transition metal-catalysed intramolecular C–H activation. Herein, we disclose an efficient macrocyclization strategy via Pd-catalysed remote meta-C–H olefination using a practical indolyl template. This approach was successfully employed to access macrolides and coumarins. In addition, the intermolecular meta-C–H olefination also worked well and was exemplified by the synthesis of antitumor drug belinostat from inexpensive and readily available benzenesulfonyl chloride. Notably, catalytic copper acetate and molecular oxygen were used in place of silver salts as oxidants. Furthermore, for the first time, the formation of a macrocyclophane cyclopalladated intermediate was detected through in situ Fourier-transform infrared monitoring experiments and ESI-MS.

Graphical abstract: Macrocyclization via remote meta-selective C–H olefination using a practical indolyl template

Supplementary files

Article information

Article type
Edge Article
Submitted
31 мар 2023
Accepted
03 июл 2023
First published
07 июл 2023
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY-NC license

Chem. Sci., 2023,14, 8279-8287

Macrocyclization via remote meta-selective C–H olefination using a practical indolyl template

P. Zhang, Z. Jiang, Z. Fan, G. Li, Q. Ma, J. Huang, J. Tang, X. Xu, J. Yu and Z. Jin, Chem. Sci., 2023, 14, 8279 DOI: 10.1039/D3SC01670F

This article is licensed under a Creative Commons Attribution-NonCommercial 3.0 Unported Licence. You can use material from this article in other publications, without requesting further permission from the RSC, provided that the correct acknowledgement is given and it is not used for commercial purposes.

To request permission to reproduce material from this article in a commercial publication, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party commercial publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements