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

页码：3509 / 3514

页数：6

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