24223-45-8Relevant academic research and scientific papers
Intramolecular metal-free oxidative aryl-aryl coupling: An unusual hypervalent-iodine-mediated rearrangement of 2-substituted n-phenylbenzamides
Shang, Siyun,Zhang-Negrerie, Daisy,Du, Yunfei,Zhao, Kang
, p. 6216 - 6219 (2014/06/23)
Hypervalent-iodine-mediated oxidative coupling of the two aryl groups in either 2-acylamino-N-phenyl-benzamides or 2-hydroxy-N-phenylbenzamides, with concomitant insertion of the ortho-substituted N or O atom into the tether, has been described for the first time. This unusual metal-free rearrangement reaction involves an oxidative C(sp2)?C(sp2) aryl-aryl bond formation, cleavage of a C(sp2)?C(O) bond, and a lactamization/lactonization. Furthermore, unsymmetrical diaryl compounds can be easily obtained by removing the tether within the cyclized product.
Synthesis of tertiary amides from anionically activated aromatic trifluoromethyl groups
OMahony, Gavin,Pitts, Andrew K.
supporting information; experimental part, p. 2024 - 2027 (2010/06/21)
Figure presented In this paper, a novel synthesis of tertiary amides from anionically activated aromatic trifluoromethyl groups is presented. Anionically activated trifluoromethyl groups react with secondary amines under aqueous conditions to afford tertiary amides. The mechanism involves initial elimination of hydrogen fluoride by an E1cB mechanism to afford an electrophilic quinone methide- or azafulvene-type intermediate that reacts with secondary amines under aqueous conditions to afford the tertiary amide in good yield (up to 99%).
