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

页码：775 / 780

页数：11

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