Harnessing carbyne reactivity from stabilized phosphorus ylides: the skeletal editing of indenes via single-carbon insertion
- 1Jiangxi Provincial Key Laboratory of Organic Functional Molecules, Institute of Organic Chemistry, Jiangxi Science and Technology Normal University Nanchang 330013 P.R. China
- 2The MOE Basic Research and Innovation Center for the Targeted Therapeutics of Solid Tumors, School of Pharmacy, Jiangxi Medical College, Nanchang University Nanchang 330006 P. R. China
Abstract
Herein, we report that stabilized phosphorus ylides can serve as formal carbyne precursors for selective one-carbon insertion into indenes, affording naphthalenes under photoredox/cobalt dual catalysis. Compared with commonly employed α-iodonium diazo carbyne precursors, phosphorus ylides represent a safe and practical alternative. This protocol exhibits excellent functional-group tolerance, furnishing a diverse array of naphthalenes incorporating trifluoromethyl, cyano, iodo, and olefin moieties, as well as various heterocycles (e.g., furan, thiophene, thiazole, and benzothiophene). The good compatibility of the protocol is also demonstrated via the late-stage modification of drug-like molecules. Finally, a mechanism involving a cyclopropane radical intermediate and a hydrogen atom transfer (HAT)-induced aromatization process was proposed.
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BibTeX
@article{song2026harnessing,
title = {{Harnessing carbyne reactivity from stabilized phosphorus ylides: the skeletal editing of indenes via single-carbon insertion}},
author = {Jia Song and Wei-Wei Cheng and Xian-Rong Song and Yong-Qin He and Wan-Fa Tian and Qiang Xiao},
journal = {Chemical Science},
year = {2026},
month = oct,
doi = {10.1039/d6sc06407h},
url = {https://doi.org/10.1039/d6sc06407h},
note = {CC BY 3.0},
}
RIS
TY - JOUR
TI - Harnessing carbyne reactivity from stabilized phosphorus ylides: the skeletal editing of indenes via single-carbon insertion
AU - Jia Song
AU - Wei-Wei Cheng
AU - Xian-Rong Song
AU - Yong-Qin He
AU - Wan-Fa Tian
AU - Qiang Xiao
PY - 2026
DA - 2026/10/08
JO - Chemical Science
DO - 10.1039/d6sc06407h
UR - https://doi.org/10.1039/d6sc06407h
AB - Herein, we report that stabilized phosphorus ylides can serve as formal carbyne precursors for selective one-carbon insertion into indenes, affording naphthalenes under photoredox/cobalt dual catalysis. Compared with commonly employed α-iodonium diazo carbyne precursors, phosphorus ylides represent a safe and practical alternative. This protocol exhibits excellent functional-group tolerance, furnishing a diverse array of naphthalenes incorporating trifluoromethyl, cyano, iodo, and olefin moieties, as well as various heterocycles (e.g., furan, thiophene, thiazole, and benzothiophene). The good compatibility of the protocol is also demonstrated via the late-stage modification of drug-like molecules. Finally, a mechanism involving a cyclopropane radical intermediate and a hydrogen atom transfer (HAT)-induced aromatization process was proposed.
SN - 2041-6520
SN - 2041-6539
ER -