Synthesis of gem-Difluoroalkenes via Nickel-Catalyzed Reductive C-F and C-O Bond Cleavage

被引：104
|
作者：
Lin, Zhiyang [1 ]
Lan, Yun [1 ]
Wang, Chuan [1 ]
机构：
[1] Univ Sci & Technol China, Hefei Natl Lab Phys Sci Microscale, Dept Chem, Ctr Excellence Mol Synth, Hefei 230026, Anhui, Peoples R China
来源：
ACS CATALYSIS | 2019年 / 9卷 / 01期
基金：
中国国家自然科学基金;
关键词：
gem-difluoroalkenes; C-F bond Cleavage; C-O bond cleavage; reductive cross-coupling; acetals; NUCLEOPHILIC 5-ENDO-TRIG CYCLIZATION; DIFLUOROMETHYL 2-PYRIDYL SULFONE; DIAZO-COMPOUNDS; FUNCTIONALIZED 1,1-DIFLUORO-1-ALKENES; ORGANOLITHIUM REAGENTS; BIOLOGICAL-ACTIVITY; CONCISE SYNTHESIS; DIFLUOROOLEFINATION; DIFLUOROCARBENE; ACTIVATION;
D O I：
10.1021/acscatal.8b04348
中图分类号：
O64 [物理化学（理论化学）、化学物理学];
学科分类号：
070304 ; 081704 ;
摘要：
By merging C-O and C-F bond cleavage in cross-electrophile coupling, we developed a method for efficient synthesis of gem-difluoroalkenes with an alkoxy-substituent on the homoallylic position using easily accessible acetals as coupling partners with alpha-trifluoromethyl alkenes. Remarkably, this Ni-catalyzed allylic defluorinative cross-coupling reaction demonstrates high tolerance of a wide range of sensitive functional groups and proves to be applicable in late-stage functionalization of structurally complex compounds.
引用
收藏
页码：775 / 780
页数：11
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