209912-24-3Relevant academic research and scientific papers
One-carbon homologation of carboxylic acids via BtCH2TMS: A safe alternative to the Arndt-Eistert reaction
Katritzky,Zhang,Haleem,Hussein,Fang,Steel
, p. 5606 - 5612 (2007/10/03)
Carboxylic acids are converted into the corresponding homologated acids or esters, using easily available 1-(trimethylsilylmethyl)benzotriazole (1) as a one-carbon synthon. The effectiveness of the reaction has been investigated on six aryl and seven alkyl carboxylic acids.
BtCH2TMS-assisted Homologation of Carboxylic Acids: A Safe Alternative to the Arndt-Eistert Reaction
Katritzky, Alan R.,Zhang, Suoming,Fang, Yunfeng
, p. 3789 - 3791 (2007/10/03)
formula presented One-carbon homologation of carboxylic acids is achieved by (i) treatment of an acyl chloride with 1-[(trimethylsilyl)methyl]-1H-1,2,3,-benzotriazole (BtCH2TMS) (1) to afford N-(acylmethyl)benzotriazoles 3a-f, followed by (ii) conversion of 3a-f with triflic anhydride into RC(OTf)=CHBt 4a-f, and (iii) the subsequent reaction of 4a-c with NaOCH3 followed by 1N HCl to afford esters RCH2CO2R′ 7a-c in overall yields of 50-70%. For the aliphatic compounds 5d-f, treatment of 5d-f with p-toluenesulfonic acid followed by TBAF/THF afforded acids RCH2COOH 7d-f.
A convenient synthesis of new 1-alkynyl-1H-benzotriazoles by reaction of alkynyl(phenyl)iodonium salts with benzotriazole ion
Kitamura, Tsugio,Tashi, Norihiko,Tsuda, Kuniyuki,Chen, Haiying,Fujiwara, Yuzo
, p. 303 - 312 (2007/10/03)
The reaction of arylethynyl(phenyl)iodonium tosylates with benzotriazole ion gave new 1-alkynyl-1H-benzotriazoles in good yields. This result indicates that alkynyliodonium salts can be used for direct alkynylation of benzotriazole. However, the similar reactions of (tert- butylethynyl)(phenyl)iodonium and 1-octynyl(phenyl)iodonium tosylates do not afford the 1-alkynyl-1H-benzotriazoles but alkenylbenzotriazoles via the reaction of alkylidenecarbenes.
Alkynylbenzotriazoles by direct alkynylation of benzotriazole using alkynyliodonium salts
Kitamura, Tsugio,Tashi, Norihiko,Tsuda, Kuniyuki,Fujiwara, Yuzo
, p. 3787 - 3790 (2007/10/03)
Alkynyl(phenyl)iodonium salts react with benzotriazole ion prepared from benzotriazole and potassium t-butoxide to give 1-alkynylbenzotriazoles in good yields, indicating that the alkynyliodonium salts can be used for direct alkynylation of benzotriazole.
