Iron-Catalyzed Allylic Defluorinative Ketone Olefin Coupling

被引：25
作者：
Zhang, Chang [1 ]
Wang, Lin [1 ]
Shi, Hongzhang [1 ]
Lin, Zhiyang [1 ]
Wang, Chuan [1 ,2 ]
机构：
[1] Univ Sci & Technol China, Dept Chem, Hefei 230026, Anhui, Peoples R China
[2] Ctr Excellence Mol Synth CAS, Hefei 230026, Anhui, Peoples R China
来源：
ORGANIC LETTERS | 2022年 / 24卷 / 17期
基金：
中国国家自然科学基金;
关键词：
ELECTROORGANIC CHEMISTRY; REDUCTIVE CYCLIZATION; GAMMA-BUTYROLACTONES; GEM-DIFLUOROALKENES; BIOLOGICAL-ACTIVITY; ORGANIC-SYNTHESIS; DIAZO-COMPOUNDS; ALDEHYDES; DIFLUOROCARBENE; TRIFLUOROMETHYL;
D O I：
10.1021/acs.orglett.2c00979
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
In this protocol, we demonstrate our discovery that iron is able to efficiently catalyze the reductive allylic defluorinative ketyl olefin coupling reaction between alpha-trifluoromethyl alkenes and unactivated ketones. This operationally simple cross-electrophile reaction circumvents the use of pre-generated organometallics and allows for the synthesis of diverse functional-group-rich tertiary gem-difluorohomoallylic alcohols through a polarity-reversed strategy. Preliminary mechanistic studies support a mechanism that proceeds through a ketyl formation/olefin insertion/beta-fluoro elimination sequence.
引用
收藏
页码：3211 / 3216
页数：6
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