56500-48-2Relevant academic research and scientific papers
An effective method for the synthesis of carboxylic esters and lactones using substituted benzoic anhydrides with Lewis acid catalysts
Shiina, Isamu
, p. 1587 - 1599 (2007/10/03)
An efficient mixed-anhydride method for the synthesis of carboxylic esters and lactones using benzoic anhydride having electron withdrawing substituent(s) is developed by the promotion of Lewis acid catalysts. In the presence of a catalytic amount of TiCl2(ClO4)2, various carboxylic esters are prepared in high yields through the formation of the corresponding mixed-anhydrides from 3,5-bis(trifluoromethyl)benzoic anhydride and carboxylic acids. The combined catalyst consisting of TiCl 2(ClO4)2 together with chlorotrimethylsilane functions as an effective catalyst for the synthesis of carboxylic esters from free carboxylic acids and alcohols with 4-(trifluoromethyl)benzoic anhydride. Various macrolactones are prepared from the free ω-hydroxycarboxylic acids by the combined use of 4-(trifluoromethyl)benzoic anhydride and titanium(IV) catalysts together with chlorotrimethylsilane under mild reaction conditions. The lactonization of trimethylsilyl ω-(trimethylsiloxy) carboxylates using 4-(trifluoromethyl)benzoic anhydride is also promoted at room temperature in the presence of a catalytic amount of TiCl 2(ClO4)2. An 8-membered ring lactone, a synthetic intermediate of cephalosporolide D, is successfully synthesized according to this mixed-anhydride method using 4-(trifluoromethyl)benzoic anhydride by the promotion of a catalytic amount of Hf(OTf)4.
A New and Efficient Esterification Reaction via Mixed Anhydrides by the Promotion of a Catalytic Amount of Lewis Acid
Miyashita, Mitsutomo,Shiina, Isamu,Miyoshi, So,Mukaiyama, Teruaki
, p. 1516 - 1527 (2007/10/02)
In the presence of a catalytic amount of Lewis acid, various carboxylic esters or S-phenyl carbothioates are prepared in excellent yields by the respective reactions of equimolar amounts of silyl carboxylates and alkyl silyl ethers or phenyl silyl sulfides with 4-trifluoromethylbenzoic anhydride.
An Efficient Method for the Preparation of Carboxylic Esters via Mixed Anhydrides by the Promotion of a Catalytic Amount of Lewis Acid
Mukaiyama, Teruaki,Shiina, Isamu,Miyashita, Mitsutomo
, p. 625 - 628 (2007/10/02)
Various carboxylic esters are prepared in excellent yields by the reaction of nearly equimolar amounts of silyl derivatives of carboxylic acids and alcohols with p-trifluoromethylbenzoic anhydride in the presence of a catalytic amount of Lewis acid.
CESIUM FLUORIDE-PROMOTED SYNTHESIS OF CARBOXYLIC ACID DERIVATIVES USING 2-FLUOROPYRIDINIUM SALT
Shoda, Shin-ichiro,Mukaiyama, Teruaki
, p. 391 - 392 (2007/10/02)
In the presence of cesium fluoride, the equimolecular reactions of carboxylic acids with alcohols, amines or thiols using 2-fluoro-pyridinium salt proceeded smoothly under mild conditions to afford the corresponding carboxylic acid derivatives with base s
