55334-41-3Relevant academic research and scientific papers
Metal-free amidation of carboxylic acids with tertiary amines
Phakhodee, Wong,Wangngae, Sirilak,Pattarawarapan, Mookda
, p. 60287 - 60290 (2016/07/11)
A direct amidation of carboxylic acids with tertiary amines could be carried out in the presence of the Ph3P-I2 activator. With an appropriate reagent addition sequence, a range of carboxylic acids including aliphatic, allylic, and aromatic acids could be converted into their corresponding tertiary amides under mild conditions without requirement of metal catalysis.
Metal-free tandem oxidative aryl migration and C-C bond cleavage: Synthesis of α-ketoamides and esters from acrylic derivatives
Liu, Le,Du, Liang,Zhang-Negrerie, Daisy,Du, Yunfei,Zhao, Kang
supporting information, p. 5772 - 5775 (2015/02/19)
A novel tandem metal-free oxidative aryl migration/C-C bond-cleavage reaction, mediated by hypervalent iodine reagent, has been discovered. The presented transformation provided straightforward access to important α-ketoamide and α-ketoester derivatives from readily available acrylic derivatives via a concerted process of 1,2-aryl shift concomitant with C-C bond cleavage.
Synthesis of β-monosubstituted α,β-unsaturated amides with z-selectivity using diphenylphosphonoacetamides
Kojima, Satoshi,Hidaka, Tsugihiko,Ohba, Yuko
, p. 515 - 523 (2007/10/03)
The utility of diphenylphosphonoacetamides [(PhO)2P(O)CH 2CONRR′] as Horner-Wadsworth-Emmons reagents was examined with five different patterns of substitution upon the amide nitrogen atom (2a: R, R′ = CH2Ph; 2b: R = CH2Ph, R′ = H; 2c: R = Me, R′ = OMe; 2d: R, R′ = Ph; 2e: R, R′ = (CH2) 4). The reaction of 2a was found to be Z-selective for aromatic aldehydes with selectivities up to 95:5. Reagent 2b led to reasonable selectivity for both benzaldehyde (85:15) and 3-phenylpropionaldehyde (87:13), while 2c was somewhat effective for only the latter alkyl aldehyde (83:17). Compounds 2d and 2e exhibited slightly lower selectivities compared with 2a.
