Generation of ε,ε-Difluorinated Metal-Pentadienyl Species through Lanthanide-Mediated C-F Activation

被引：22

作者：

Kumar, Tarun ^{[1
]}

Massicot, Fabien ^{[1
]}

Harakat, Dominique ^{[1
]}

Chevreux, Sylviane ^{[1
]}

Martinez, Agathe ^{[1
]}

Bordolinska, Klaudia ^{[1
]}

Preethalayam, Preethanuj ^{[2
]}

Vasu, Radhakrishnan Kokkuvayil ^{[2
]}

Behr, Jean-Bernard ^{[1
]}

Vasse, Jean-Luc ^{[1
]}

Jaroschik, Florian ^{[1
]}

机构：

[1] Univ Reims, Inst Chim Mol Reims, CNRS UMR 7312, BP 1039, F-51687 Reims 2, France

[2] CSIR, Natl Inst Interdisciplinary Sci & Technol, Organ Chem Sect, Thiruvananthapuram 695019, Kerala, India

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2017年 / 23卷 / 65期

关键词：

C-F activation; difluoroalkenes; lanthanides; pentadienyl complexes; spirocycles; ALLYLIC ALUMINUM REAGENTS; CARBONYL-COMPOUNDS; BOND ACTIVATION; ORGANIC-SYNTHESIS; KETONES; COMPLEXES; ALDEHYDES; ANIONS; POTENT; ELECTROPHILES;

D O I：

10.1002/chem.201704322

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Heavy metal on Lewis acid: The combination of lanthanide metals and AlCl3 has been employed for selective single C-F activation in benzofulvenes comprising an exocyclic CF3 substituent. Intermediate epsilon,epsilon-difluorinated metal-dienyl species react with a large variety of aldehydes in a highly regio- and diastereoselective fashion to afford 1,1-disubstituted indenes bearing a difluorovinyl group. These new building blocks have been further transformed through a hydrogenation-cyclization process into fluorinated heterocyclic spiro compounds.

引用

页码：16460 / 16465

页数：6

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