1598437-64-9Relevant articles and documents
Steric and Electronic Effects in the Synthesis and Regioselective Hydrolysis of Unsymmetrical Imides
Shang, Jing,Pourvali, Aysa,Cochrane, James R.,Hutton, Craig A.
, p. 1854 - 1858 (2015/12/26)
The AgI-promoted coupling reaction of thioamides and carboxylic acids is shown to be a useful method for the generation of unsymmetrical imides. The reaction proceeds efficiently with unhindered and electron-rich or neutral coupling partners, but not with hindered thioamides (such as thiopivalamides) or electron deficient thioamides (such as trifluorothioacetamides). Intriguingly, thioformamides are also ineffective coupling partners, despite having minimal steric or electronic influence. Hindered carboxylic acid coupling partners (such as pivalic acid) are tolerated, but electron deficient acids, such as trifluoroacetic acid, are ineffective coupling partners. Furthermore, an interplay of both steric and electronic effects is observed in the subsequent hydrolysis of unsymmetrical imides. Imides with a dimethoxybenzoyl group give high regioselectivity upon hydrolysis, favouring cleavage of the distal acyl group. Imides with a p-nitrobenzoyl or pivaloyl group give reversed selectivity, favouring cleavage of the proximal acyl group.
Fe-Catalysed oxidative C-H/N-H coupling between aldehydes and simple amides
Wang, Jing,Liu, Chao,Yuan, Jiwen,Lei, Aiwen
supporting information, p. 4736 - 4739 (2014/05/06)
A novel oxidative coupling of aldehydes with simple amides, most likely involving a radical process, was achieved through the use of an iron catalyst. Various amides were utilized as substrates to easily construct imides by coupling with aldehydes. A catalytic cycle involving the benzoyl halide intermediate is proposed based on our experimental results. This journal is the Partner Organisations 2014.
