Chemoselective N- and O-Difluoromethylation of 2-Pyridones, Isoquinolinones, and Quinolinones with TMSCF2Br

被引：21
作者：
Zhu, Ziyue [1 ,2 ]
Krishnamurti, Vinayak [1 ,2 ]
Ispizua-Rodriguez, Xanath [1 ,2 ]
Barrett, Colby [1 ,2 ]
Prakash, G. K. Surya [1 ,2 ]
机构：
[1] Univ Southern Calif, Loker Hydrocarbon Res Inst, Los Angeles, CA 90089 USA
[2] Univ Southern Calif, Dept Chem, Los Angeles, CA 90089 USA
来源：
ORGANIC LETTERS | 2021年 / 23卷 / 16期
关键词：
NUCLEOPHILIC DIFLUOROMETHYLATION; DIFLUOROCARBENE; REAGENT; POTENT;
D O I：
10.1021/acs.orglett.1c02305
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An operationally simple protocol for direct N- and O-difluoromethylation of 2-pyridones, quinolinones, and isoquinolinones using commercially available TMSCF2Br is disclosed. The chemoselectivity is modulated by simple variations in temperature, solvent, and strength of the base. Diverse, synthetically relevant functional groups are tolerated, including functional groups that have reported reactivity with TMSCF2Br. Gram-scale reactions to prepare both N- and O-difluoromethyl compounds are included.
引用
收藏
页码：6494 / 6498
页数：5
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