New Parallel Synthesis of Di(hetero)arylamides
David S. Grierson describes a new synthesis for di(hetero)arylamides starting from N-TMS derivatives of weakly nucleophilic heteroaryl/arylamines.
A Trimethylsilylamine-Acyl Fluoride Amide Bond Forming Protocol for Weakly Nucleophilic Amines that is Amenable to the Parallel Synthesis of Di(hetero)arylamides: M. Zamiri, D. S. Grierson
Synthesis 2016, DOI: 10.1055/s-0036-1588603
The synthesis of amides derived from poorly nucleophilic heteroarylamines, such as those having an azine substituent, can be inefficient and low-yielding. For this reason, novel user-friendly procedures for the preparation of the title compounds are in demand. The group of Professor David Grierson from The University of British Columbia (Vancouver, Canada) has recently reported a new protocol that should represent a useful addition to the arsenal of methods available for the synthesis of di(hetero)arylamides.
Professor Grierson said:
“In contrast to the use of traditional peptide coupling protocols, the reaction of the N-TMS derivatives of weakly nucleophilic heteroaromatic and electron-deficient aromatic amines with readily prepared and stable acid fluorides in acetonitrile (TBAF catalysis) provides an operationally simple and efficient means to prepare libraries of otherwise difficult to obtain bis(hetero)aromatic amines in pure form.”
