Visible Light-Promoted Aromatization-Driven Deconstructive Fluorination of Spiro Carbocycles

Wen Peng Yang; Hong Jie Miao; Le Liu; Xin Hua Duan; Li Na Guo

doi:10.1021/acs.orglett.4c02793

Visible Light-Promoted Aromatization-Driven Deconstructive Fluorination of Spiro Carbocycles

Wen Peng Yang
, Hong Jie Miao
, Le Liu
, Xin Hua Duan
, Li Na Guo

School of Chemistry

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

21 Scopus citations

Abstract

A visible light-promoted aromatization-driven deconstructive fluorination of spiro carbocycles is presented. A series of spiro dihydroquinazolinones reacted efficiently with NFSI under visible light irradiation to afford the 2-(4-fluoroalkyl)quinazolin-4(3H)-ones in good yields with excellent functional group tolerance. A radical pathway involving C-C bond cleavage and F atom transfer is proposed for the reaction. In addition, the ring-opening chlorination of spiro dihydroquinazolinones with NCS was also applicable.

Original language	English
Pages (from-to)	7442-7446
Number of pages	5
Journal	Organic Letters
Volume	26
Issue number	35
DOIs	https://doi.org/10.1021/acs.orglett.4c02793
State	Published - 6 Sep 2024

Access to Document

10.1021/acs.orglett.4c02793

Cite this

@article{a20386113fbb49278a8c42962aac8a83,

title = "Visible Light-Promoted Aromatization-Driven Deconstructive Fluorination of Spiro Carbocycles",

abstract = "A visible light-promoted aromatization-driven deconstructive fluorination of spiro carbocycles is presented. A series of spiro dihydroquinazolinones reacted efficiently with NFSI under visible light irradiation to afford the 2-(4-fluoroalkyl)quinazolin-4(3H)-ones in good yields with excellent functional group tolerance. A radical pathway involving C-C bond cleavage and F atom transfer is proposed for the reaction. In addition, the ring-opening chlorination of spiro dihydroquinazolinones with NCS was also applicable.",

author = "Yang, \{Wen Peng\} and Miao, \{Hong Jie\} and Le Liu and Duan, \{Xin Hua\} and Guo, \{Li Na\}",

note = "Publisher Copyright: {\textcopyright} 2024 American Chemical Society.",

year = "2024",

month = sep,

day = "6",

doi = "10.1021/acs.orglett.4c02793",

language = "英语",

volume = "26",

pages = "7442--7446",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "35",

}

TY - JOUR

T1 - Visible Light-Promoted Aromatization-Driven Deconstructive Fluorination of Spiro Carbocycles

AU - Yang, Wen Peng

AU - Miao, Hong Jie

AU - Liu, Le

AU - Duan, Xin Hua

AU - Guo, Li Na

PY - 2024/9/6

Y1 - 2024/9/6

N2 - A visible light-promoted aromatization-driven deconstructive fluorination of spiro carbocycles is presented. A series of spiro dihydroquinazolinones reacted efficiently with NFSI under visible light irradiation to afford the 2-(4-fluoroalkyl)quinazolin-4(3H)-ones in good yields with excellent functional group tolerance. A radical pathway involving C-C bond cleavage and F atom transfer is proposed for the reaction. In addition, the ring-opening chlorination of spiro dihydroquinazolinones with NCS was also applicable.

AB - A visible light-promoted aromatization-driven deconstructive fluorination of spiro carbocycles is presented. A series of spiro dihydroquinazolinones reacted efficiently with NFSI under visible light irradiation to afford the 2-(4-fluoroalkyl)quinazolin-4(3H)-ones in good yields with excellent functional group tolerance. A radical pathway involving C-C bond cleavage and F atom transfer is proposed for the reaction. In addition, the ring-opening chlorination of spiro dihydroquinazolinones with NCS was also applicable.

UR - https://www.scopus.com/pages/publications/85202461204

U2 - 10.1021/acs.orglett.4c02793

DO - 10.1021/acs.orglett.4c02793

M3 - 文章

C2 - 39186378

AN - SCOPUS:85202461204

SN - 1523-7060

VL - 26

SP - 7442

EP - 7446

JO - Organic Letters

JF - Organic Letters

IS - 35

ER -

Visible Light-Promoted Aromatization-Driven Deconstructive Fluorination of Spiro Carbocycles

Abstract

Access to Document

Other files and links

Fingerprint

Cite this