Ni(0)-Catalyzed Three-Component Coupling Reaction of Tetrafluoroethylene and N‑Sulfonyl-Substituted Imines with Silanes via Aza-Nickelacycles

A nickel-catalyzed three-component coupling reaction of tetrafluoroethylene (TFE) and N-sulfonyl-substituted imines with silanes that furnishes a variety of fluorine-containing amines is disclosed. Stoichiometric experiments revealed that the aza-nickelacycles generated upon oxidative cyclization of...

Full description

Saved in:
Bibliographic Details
Published in:Organic letters 2019-02, Vol.21 (4), p.851-856
Main Authors: Shirataki, Hiroshi, Ono, Takafumi, Ohashi, Masato, Ogoshi, Sensuke
Format: Article
Language:English
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:A nickel-catalyzed three-component coupling reaction of tetrafluoroethylene (TFE) and N-sulfonyl-substituted imines with silanes that furnishes a variety of fluorine-containing amines is disclosed. Stoichiometric experiments revealed that the aza-nickelacycles generated upon oxidative cyclization of TFE and N-sulfonyl-substituted imines on Ni(0) were identified as the key intermediates in this catalytic reaction. A single-crystal X-ray diffraction analysis of such an aza-nickelacycle revealed that the O atom of the N-sulfonyl group stabilizes the key intermediate via coordination to the nickel center.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.8b03674