Thiochromane Formation via Visible-Light-Mediated Intramolecular ?-C(sp3)-H Bond Arylation of Sulfonamides

被引：3
|
作者：
Liu, Shuai [1 ]
Kumar, Nivesh [1 ]
Robert, Frederic [1 ]
Landais, Yannick [1 ]
机构：
[1] Univ Bordeaux, CNRS, Bordeaux INP, ISM,UMR 5255, F-33400 Talence, France
来源：
ORGANIC LETTERS | 2023年 / 25卷 / 17期
关键词：
C-H BONDS; FUNCTIONALIZATION; HETEROARYLATION; ALKYLATION; ANION;
D O I：
10.1021/acs.orglett.3c00900
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Visible-light-mediated intramolecular site-selective delta-C(sp3)-H bond arylation of aliphatic trifluoromethanesulfona-mides was developed. The reaction proceeds through a radical cascade, including the generation of a sulfonamidyl radical, which triggers a 1,5-hydrogen atom transfer, affording a delta-C-centered radical, which finally cyclized onto a neighboring thiopolyfluoroaryl moiety to deliver a range of synthetically useful thiochromanes. The cyclization process occurs through two distinct pathways depending upon the nature of the substituent X ortho to the native C-S bond.
引用
收藏
页码：3072 / 3077
页数：6
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