Citation: Yu-Chen Fang, Jia-He Chen, Mi-Zhuan Li, Hui-Min Li, Mei Bai, Yong-Zheng Chen, Zi-Wei Gao, Wen-Yong Han. Forging of silaoxycarbocyclics by interrupted Catellani reaction[J]. Chinese Chemical Letters, ;2025, 36(7): 110474. doi: 10.1016/j.cclet.2024.110474 shu

Forging of silaoxycarbocyclics by interrupted Catellani reaction

Yu-Chen Fang ^{a, b} ,
Jia-He Chen ^b ,
Mi-Zhuan Li ^c ,
Hui-Min Li ^b ,
Mei Bai ^b ,
Yong-Zheng Chen ^b ,
Zi-Wei Gao ^{a, d, *,} ,
Wen-Yong Han ^{b, *,}

a.
School of Chemistry & Chemical Engineering, Xinjiang Normal University, Urumqi 830054, China
b.
Key Laboratory of Biocatalysis & Chiral Drug Synthesis of Guizhou Province, Generic Drug Research Center of Guizhou Province, School of Pharmacy, Zunyi Medical University, Zunyi 563006, China
c.
School of Public Health, Zunyi Medical University, Zunyi 563006, China
d.
Key Laboratory of Applied Surface and Colloid Chemistry, Xi'an Key Laboratory of Organometallic Material Chemistry, School of Chemistry and Chemical Engineering, Shaanxi Normal University, Xi'an 710119, China

zwgao@snnu.edu.cn

hanwy@126.com

Received Date: 10 June 2024
Revised Date: 17 September 2024
Accepted Date: 18 September 2024
Available Online: 21 September 2024

Figures(7)

Catalytic syntheses of silaoxycarbocyclics from an interrupted Catellani reaction of 3-iodochromones with bridged olefins and octamethyl-1, 4-dioxacyclohexasilane is described. This protocol involves the oxidative addition of chromonyl-norbornyl-palladacycle generated through successive oxidative addition of Pd(0) to 3-iodochromones, migratory insertion of NBE and intramolecular ortho-C(sp²)−H activation to the tetrasilane, thus motivating a (4 + 6) annulation and ring expansion. The synthetic practicality of current strategy is further proved by the late-stage modification of pharmaceuticals and natural products, gram-scale experiments, as well as the transformations of functional groups of silaoxycarbocyclics.
- Ring expansion,
- Chromonyl-norbornyl-palladacycle,
- Interrupted Catellani reaction,
- Silaoxycarbocyclics
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