We found a match
Your institution may have rights to this item. Sign in to continue.
- Title
Transition‐Metal Free Catalytic Synthesis of Trifluoromethyl Indolines by [4+1] Cycloaddition of Trifluoromethyl Benzoxazinones with Sulfur Ylides.
- Authors
Kawai, Koki; Uno, Hiroto; Fujimoto, Daichi; Shibata, Norio
- Abstract
Stereoselective catalytic synthesis of 3‐trifluoromethyl indolines through the [4+1] cycloaddition of benzoxazinones and sulfur ylides in a transition‐metal‐free manner was developed. In the presence of a catalytic amount of sodium hydride, aza‐ortho‐quinone methide intermediates were formed from trifluoromethyl benzoxazinones through decarboxylation after the first nucleophilic attack of sulfur ylides, which progressed to a second nucleophilic attack of sulfur ylides, resulting in the [4+1] cycloaddition. The key for this catalytic transformation is the dual attack of sulfur ylides on substrates. This unique transition‐metal‐free protocol is applicable to the synthesis of non‐fluorinated vinyl‐, ethynyl‐ or methyl‐substituted indolines. The synthesis of 3‐trifluoromethyl indoles was also achieved described under stoichiometric conditions.
- Subjects
BENZOXAZINONES; INDOLINE; YLIDES; TRANSITION metals; RING formation (Chemistry); SULFUR; SODIUM hydride
- Publication
Helvetica Chimica Acta, 2021, Vol 104, Issue 1, p1
- ISSN
0018-019X
- Publication type
Article
- DOI
10.1002/hlca.202000217