Iron(III)-promoted hydrofunctionalization/bicyclization of 1,7-enynes toward benzo[a]fluoren-5-ones

Min Hua Huang; Yu Hong; Jian Qiang Hu; Shi Zhao Yang; Yi Long Zhu; De Cai Wang; Bo Jiang

doi:10.1016/j.tetlet.2019.151507

Iron(III)-promoted hydrofunctionalization/bicyclization of 1,7-enynes toward benzo[a]fluoren-5-ones

Min Hua Huang, Yu Hong, Jian Qiang Hu, Shi Zhao Yang, Yi Long Zhu, De Cai Wang, Bo Jiang

School of Pharmaceutical Sciences

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

8 Scopus citations

Abstract

A new hydrofunctionalization/bicyclization of C(sp³)-tethered 1,7-enynes toward benzo[a]fluoren-5-ones with good to excellent yields has been developed by using Iron(III)/PhSiH₃ system as a hydride donor. This protocol involves a reductive 1,7-enyne-carboannulation cascade, leading to C(sp³)[sbnd]H and C[sbnd]C bond-forming events to rapidly build up tetracarbocyclic complexity. A wide range of functional groups relative to 1,7-enyne substrates were tolerated well under mild neutral-redox conditions.

Original language	English
Article number	151507
Journal	Tetrahedron Letters
Volume	61
Issue number	7
DOIs	https://doi.org/10.1016/j.tetlet.2019.151507
State	Published - 13 Feb 2020

Keywords

Benzo[a]fluoren-5-ones
Bicyclization
Hydrofunctionalization
Radical chemistry

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10.1016/j.tetlet.2019.151507

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title = "Iron(III)-promoted hydrofunctionalization/bicyclization of 1,7-enynes toward benzo[a]fluoren-5-ones",

abstract = "A new hydrofunctionalization/bicyclization of C(sp3)-tethered 1,7-enynes toward benzo[a]fluoren-5-ones with good to excellent yields has been developed by using Iron(III)/PhSiH3 system as a hydride donor. This protocol involves a reductive 1,7-enyne-carboannulation cascade, leading to C(sp3)[sbnd]H and C[sbnd]C bond-forming events to rapidly build up tetracarbocyclic complexity. A wide range of functional groups relative to 1,7-enyne substrates were tolerated well under mild neutral-redox conditions.",

keywords = "Benzo[a]fluoren-5-ones, Bicyclization, Hydrofunctionalization, Radical chemistry",

author = "Huang, {Min Hua} and Yu Hong and Hu, {Jian Qiang} and Yang, {Shi Zhao} and Zhu, {Yi Long} and Wang, {De Cai} and Bo Jiang",

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doi = "10.1016/j.tetlet.2019.151507",

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T1 - Iron(III)-promoted hydrofunctionalization/bicyclization of 1,7-enynes toward benzo[a]fluoren-5-ones

AU - Huang, Min Hua

AU - Hong, Yu

AU - Hu, Jian Qiang

AU - Yang, Shi Zhao

AU - Zhu, Yi Long

AU - Wang, De Cai

AU - Jiang, Bo

PY - 2020/2/13

Y1 - 2020/2/13

N2 - A new hydrofunctionalization/bicyclization of C(sp3)-tethered 1,7-enynes toward benzo[a]fluoren-5-ones with good to excellent yields has been developed by using Iron(III)/PhSiH3 system as a hydride donor. This protocol involves a reductive 1,7-enyne-carboannulation cascade, leading to C(sp3)[sbnd]H and C[sbnd]C bond-forming events to rapidly build up tetracarbocyclic complexity. A wide range of functional groups relative to 1,7-enyne substrates were tolerated well under mild neutral-redox conditions.

AB - A new hydrofunctionalization/bicyclization of C(sp3)-tethered 1,7-enynes toward benzo[a]fluoren-5-ones with good to excellent yields has been developed by using Iron(III)/PhSiH3 system as a hydride donor. This protocol involves a reductive 1,7-enyne-carboannulation cascade, leading to C(sp3)[sbnd]H and C[sbnd]C bond-forming events to rapidly build up tetracarbocyclic complexity. A wide range of functional groups relative to 1,7-enyne substrates were tolerated well under mild neutral-redox conditions.

KW - Benzo[a]fluoren-5-ones

KW - Bicyclization

KW - Hydrofunctionalization

KW - Radical chemistry

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DO - 10.1016/j.tetlet.2019.151507

M3 - 文章

AN - SCOPUS:85076835530

SN - 0040-4039

VL - 61

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 7

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ER -

Iron(III)-promoted hydrofunctionalization/bicyclization of 1,7-enynes toward benzo[a]fluoren-5-ones

Abstract

Keywords

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