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通过光催化产生的自由基阳离子实现未受张力的C-C键活化和定向氟化。

Unstrained C-C bond activation and directed fluorination through photocatalytically-generated radical cations.

作者信息

Pitts Cody Ross, Bloom Michelle Sheanne, Bume Desta Doro, Zhang Qinze Arthur, Lectka Thomas

机构信息

Department of Chemistry , Johns Hopkins University , Baltimore , MD , USA . Email:

出版信息

Chem Sci. 2015 Sep 1;6(9):5225-5229. doi: 10.1039/c5sc01973g. Epub 2015 Jun 23.

DOI:10.1039/c5sc01973g
PMID:29449927
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC5669245/
Abstract

Expanding the repertoire of controlled radical fluorination techniques, we present a photosensitized unstrained C-C bond activation/directed monofluorination method using Selectfluor and 9-fluorenone. The reaction is amenable to the opening of multiple 1-acetal-2-aryl substituted rings to yield ω-fluoro carboxylic acids, esters, alcohols, and ketones with relative ease. Initial mechanistic insight suggests radical ion intermediates.

摘要

我们扩展了可控自由基氟化技术的范围,提出了一种使用Selectfluor和9-芴酮的光敏无张力C-C键活化/定向单氟化方法。该反应相对容易地使多个1-缩醛-2-芳基取代的环开环,生成ω-氟代羧酸、酯、醇和酮。初步的机理研究表明存在自由基离子中间体。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d3da/5669245/e2d02b7a51f6/c5sc01973g-s5.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d3da/5669245/3a7be41c6c15/c5sc01973g-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d3da/5669245/97b8d9c279a4/c5sc01973g-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d3da/5669245/2e2cdcba644b/c5sc01973g-s3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d3da/5669245/03174d781864/c5sc01973g-s4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d3da/5669245/e2d02b7a51f6/c5sc01973g-s5.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d3da/5669245/3a7be41c6c15/c5sc01973g-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d3da/5669245/97b8d9c279a4/c5sc01973g-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d3da/5669245/2e2cdcba644b/c5sc01973g-s3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d3da/5669245/03174d781864/c5sc01973g-s4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d3da/5669245/e2d02b7a51f6/c5sc01973g-s5.jpg

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