80360-16-3Relevant academic research and scientific papers
Amide synthesis by nucleophilic attack of vinyl azides
Zhang, Feng-Lian,Wang, Yi-Feng,Lonca, Geoffroy Herve,Zhu, Xu,Chiba, Shunsuke
supporting information, p. 4390 - 4394 (2014/05/06)
A method for the synthesis of amide-containing molecules was developed using vinyl azides as an enamine-type nucleophile towards carbon electrophiles, such as imines, aldehydes, and carbocations that were generated from alcohols in the presence of BF3OEt2. After nucleophilic attack of the vinyl azide, a substituent of the resulting iminodiazonium ion intermediate migrates to form a nitrilium ion, which is hydrolyzed to afford the corresponding amide. Nitrilium intermediate: A new method for amide synthesis employs vinyl azides as enamine-type nucleophiles towards carbon electrophiles in the presence of BF3OEt2. After nucleophilic attack of the vinyl azide, a substituent of the resulting iminodiazonium ion intermediate A migrates to form nitrilium ion B, which is hydrolyzed to afford the corresponding amide.
Halogen-magnesium exchange reaction of iodoindole derivatives
Kondo, Yoshinori,Yoshida, Akihiro,Sato, Shuichiroh,Sakamoto, Takao
, p. 105 - 108 (2007/10/02)
Halogen-magnesium exchange reaction of iodoindoles with ethylmagnesium bromide in THF undergoes smoothly to give indolylmagnesium bromides which react with various electrophiles.
Preparation and reactions of lithium indolyl(dimethyl)zincates
Kondo, Yoshinori,Takazawa, Nobuo,Yoshida, Akihiro,Sakamoto, Takao
, p. 1207 - 1208 (2007/10/02)
Lithium indol-3-yl(dimethyl)zincates, prepared by halogen-zinc exchange of 3-iodo-1-phenylsulfonylindoles with lithium trimethylzincate, reacted with benzaldehyde to give the corresponding alcohols.
Generation and Reactions of 3-Lithio-1-(phenylsulfonyl)indole
Saulnier, Mark G.,Gribble, Gordon W.
, p. 757 - 761 (2007/10/02)
Treatment of 1-(phenylsulfonyl)-3-iodoindole (6) with 2 equiv of tert-butyllithium (-100 deg C THF) generates essentially quantitatively 3-lithio-1-(phenylsulfonyl)indole (1).Quenching 1 with various electrophiles gives 3-substituted indoles in good yield
