41390-40-3Relevant academic research and scientific papers
Controlled and chemoselective reduction of secondary amides
Pelletier, Guillaume,Bechara, William S.,Charette, Andre B.
supporting information; experimental part, p. 12817 - 12819 (2010/11/05)
This communication describes a metal-free methodology involving an efficient and controlled reduction of secondary amides to imines, aldehydes, and amines in good to excellent yields under ambient pressure and temperature. The process includes a chemoselective activation of a secondary amide with triflic anhydride in the presence of 2-fluoropyridine. The electrophilic activated amide can then be reduced to the corresponding iminium using triethylsilane, a cheap, rather inert, and commercially available reagent. Imines can be isolated after a basic workup or readily transformed to the aldehydes following an acidic workup. The amine moiety can be accessed via a sequential reductive amination by the addition of silane and Hantzsch ester hydride in a one-pot reaction. Moreover, this reduction tolerates various functional groups that are usually reactive under reductive conditions and is very selective to secondary amides.
A mild and efficient reaction for conversion of carboxylic acids into acid bromides with ethyl tribromoacetate/triphenylphosphine under acid-free conditions
Kang, Dong Ho,Joo, Tae Young,Lee, Eun Hwa,Chaysripongkul, Skaydaw,Chavasiri, Warinthorn,Jang, Doo Ok
, p. 5693 - 5696 (2007/10/03)
Acid bromides were prepared efficiently from carboxylic acids with readily available ethyl tribromoacetate and triphenylphosphine at room temperature under neutral conditions. The present process is applicable to the preparation of various acid bromides from aromatic and aliphatic carboxylic acids. Aromatic carboxylic acids were found to be more reactive than aliphatic carboxylic acids under reaction conditions.
A mild and efficient procedure for the preparation of acid chlorides from carboxylic acids
Jang, Doo Ok,Park, Doo Jin,Joonggon, Kim
, p. 5323 - 5326 (2007/10/03)
Various carboxylic acids are converted into the corresponding acid chlorides by treatment with trichloroacetonitrile and triphenylphosphine in methylene chloride at room temperature. Aryl acids show higher reactivity than alkyl acids under the conditions.
