Preparation of (2,2-difluoroethenylidene)bis(tributylstannane) and arylation reaction: efficient approach to 1,1-diaryl-2,2-difluoroethenes

Reaction of 2,2-difluoro-1-tributylstannylethenyl p-toluenesulfonate (1) with bis(tributyltin) in the presence of 5mol% Pd(PPh3)4 and 30equiv LiBr in THF at reflux temperature for 7h afforded (2,2-difluoroethenylidene)bis(tributylstannane) (2) in a 70% yield. Coupling reaction of 2 with aryl iodides...

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Bibliographic Details
Published in:Tetrahedron letters 2012-04, Vol.53 (14), p.1833-1836
Main Authors: Han, Seung Yeon, Lee, Hyo Young, Jeon, Jong Hee, Jeong, In Howa
Format: Article
Language:English
Subjects:
(2,2-Difluoroethenylidene)bis(tributylstannane)
2,2-Diaryl-1,1-difluoroethenes
Aromatic compounds
Arylation reaction
Chemical reactions
Iodides
Joining
Tetrahedrons
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Summary:Reaction of 2,2-difluoro-1-tributylstannylethenyl p-toluenesulfonate (1) with bis(tributyltin) in the presence of 5mol% Pd(PPh3)4 and 30equiv LiBr in THF at reflux temperature for 7h afforded (2,2-difluoroethenylidene)bis(tributylstannane) (2) in a 70% yield. Coupling reaction of 2 with aryl iodides in the presence of 5mol% Pd(PPh3)4 and 5mol% CuI in DMF at 80°C for 3–4h provided the coupled products 3 in 59–85% yields.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2012.01.127