Three-Component Bisannulation for the Synthesis of Trifluoromethylated Tetracyclic Aza-Aromatics through Six C(sp3)-F Bond Cleavage and Four C-N Bond Formation

Qing Dong Wang; Ya Wen Wang; Ting Xie; Yan Ying Cui; Mengtao Ma; Zhi Liang Shen; Xue Qiang Chu

doi:10.1021/acs.joc.1c00695

Three-Component Bisannulation for the Synthesis of Trifluoromethylated Tetracyclic Aza-Aromatics through Six C(sp³)-F Bond Cleavage and Four C-N Bond Formation

Qing Dong Wang, Ya Wen Wang, Ting Xie, Yan Ying Cui, Mengtao Ma, Zhi Liang Shen, Xue Qiang Chu

School of Chemistry and Moleculai Engineering

Research output: Contribution to journal › Article › peer-review

12 Scopus citations

Abstract

An unprecedented and expeditious tandem bisannulation of polyfluoroalkylated tetralones with benzamidines to access various fluoroalkyl tetracyclic [1,3]-diazepines through multiple C-N bond formation and C(sp3)-F bond cleavage is reported. The process features high regio-/chemoselectivities, broad substrate scope, good functional group tolerance, procedural simplicity, mild reaction conditions, and scale-up synthesis. Mechanistic studies showed that the distinctive fluorine effect of polyfluoroalkyl tetralone plays a vital role for the aza-tetracycle construction.

Original language	English
Pages (from-to)	8236-8247
Number of pages	12
Journal	Journal of Organic Chemistry
Volume	86
Issue number	12
DOIs	https://doi.org/10.1021/acs.joc.1c00695
State	Published - 18 Jun 2021

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title = "Three-Component Bisannulation for the Synthesis of Trifluoromethylated Tetracyclic Aza-Aromatics through Six C(sp3)-F Bond Cleavage and Four C-N Bond Formation",

abstract = "An unprecedented and expeditious tandem bisannulation of polyfluoroalkylated tetralones with benzamidines to access various fluoroalkyl tetracyclic [1,3]-diazepines through multiple C-N bond formation and C(sp3)-F bond cleavage is reported. The process features high regio-/chemoselectivities, broad substrate scope, good functional group tolerance, procedural simplicity, mild reaction conditions, and scale-up synthesis. Mechanistic studies showed that the distinctive fluorine effect of polyfluoroalkyl tetralone plays a vital role for the aza-tetracycle construction.",

author = "Wang, {Qing Dong} and Wang, {Ya Wen} and Ting Xie and Cui, {Yan Ying} and Mengtao Ma and Shen, {Zhi Liang} and Chu, {Xue Qiang}",

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doi = "10.1021/acs.joc.1c00695",

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T1 - Three-Component Bisannulation for the Synthesis of Trifluoromethylated Tetracyclic Aza-Aromatics through Six C(sp3)-F Bond Cleavage and Four C-N Bond Formation

AU - Wang, Qing Dong

AU - Wang, Ya Wen

AU - Xie, Ting

AU - Cui, Yan Ying

AU - Ma, Mengtao

AU - Shen, Zhi Liang

AU - Chu, Xue Qiang

PY - 2021/6/18

Y1 - 2021/6/18

N2 - An unprecedented and expeditious tandem bisannulation of polyfluoroalkylated tetralones with benzamidines to access various fluoroalkyl tetracyclic [1,3]-diazepines through multiple C-N bond formation and C(sp3)-F bond cleavage is reported. The process features high regio-/chemoselectivities, broad substrate scope, good functional group tolerance, procedural simplicity, mild reaction conditions, and scale-up synthesis. Mechanistic studies showed that the distinctive fluorine effect of polyfluoroalkyl tetralone plays a vital role for the aza-tetracycle construction.

AB - An unprecedented and expeditious tandem bisannulation of polyfluoroalkylated tetralones with benzamidines to access various fluoroalkyl tetracyclic [1,3]-diazepines through multiple C-N bond formation and C(sp3)-F bond cleavage is reported. The process features high regio-/chemoselectivities, broad substrate scope, good functional group tolerance, procedural simplicity, mild reaction conditions, and scale-up synthesis. Mechanistic studies showed that the distinctive fluorine effect of polyfluoroalkyl tetralone plays a vital role for the aza-tetracycle construction.

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M3 - 文章

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SN - 0022-3263

VL - 86

SP - 8236

EP - 8247

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 12

ER -

Three-Component Bisannulation for the Synthesis of Trifluoromethylated Tetracyclic Aza-Aromatics through Six C(sp³)-F Bond Cleavage and Four C-N Bond Formation

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