Titanocene-Catalyzed Reductive Domino Epoxide Ring Opening/Defluorinative Cross-Coupling Reaction

被引：46
|
作者：
Lin, Zhiyang [1 ,2 ]
Lan, Yun [1 ,2 ]
Wang, Chuan [1 ,2 ,3 ]
机构：
[1] Univ Sci & Technol China, Hefei Natl Lab Phys Sci Microscale, Hefei 230026, Anhui, Peoples R China
[2] Univ Sci & Technol China, Dept Chem, Hefei 230026, Anhui, Peoples R China
[3] Chinese Acad Sci, Ctr Excellence Mol Synth, Hefei 230026, Anhui, Peoples R China
来源：
ORGANIC LETTERS | 2020年 / 22卷 / 09期
基金：
中国国家自然科学基金;
关键词：
NUCLEOPHILIC 5-ENDO-TRIG CYCLIZATION; FUNCTIONALIZED GEM-DIFLUOROALKENES; DIFLUOROMETHYL 2-PYRIDYL SULFONE; STEREOSPECIFIC SYNTHESIS; ORGANOLITHIUM REAGENTS; BIOLOGICAL-ACTIVITY; 4-EXO CYCLIZATIONS; CONCISE SYNTHESIS; C-F; ALDEHYDES;
D O I：
10.1021/acs.orglett.0c00960
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Herein, we report a method for efficient synthesis of gem-difluorobishomoallylic alcohols starting from trifluoromethyl-substituted alkenes and epoxides via a titanocene-catalyzed reductive domino reaction, which consists of a Ti(III)-mediated radical-type ring opening and the following allylic defluorinative cross-coupling reaction via sequential radical addition and beta-F elimination. Notably, complete regioselectivity and high tolerance of functionalities can be achieved in this reaction. Furthermore, diverse 6-fluoro-3,4-dihydro-2H-pyrans have been prepared through derivatization of the cross-coupling products in one single step.
引用
收藏
页码：3509 / 3514
页数：6
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