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 mar 2023
Accepted
03 iyl 2023
First published
07 iyl 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

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