Phenysilane and Silicon Tetraacetate: Versatile Promotors for Amide Synthesis

Eléonore Morisset (1) , Aurélien Chardon (1) , Jacques Rouden (1) , Jerome Blanchet (1)

1 LCMT - Laboratoire de chimie moléculaire et thioorganique

Phenylsilane was reevaluated as a useful coupling reagent for amide synthesis. At room temperature, a wide range of amides and peptides were obtained in good to excellent yields (up to 99%). For the first time, Weinreb amides synthesis mediated by a hydrosilane were also documented. Comparative experiments with various acetoxysilanes suggested the involvement of a phenyl-triacyloxysilane. From this mechanistic study, silicon tetracetate was shown as an efficient amine acylating agent.

Keywords: Hydrosilane; Amides; Peptides; Acetylation; Coupling reagent

Domains: Chemical Sciences; Organic chemistry

Eléonore Morisset, Aurélien Chardon, Jacques Rouden, Jerome Blanchet. Phenysilane and Silicon Tetraacetate: Versatile Promotors for Amide Synthesis. European Journal of Organic Chemistry, 2020, 2020 (3), pp.388-392. ⟨10.1002/ejoc.201901660⟩. ⟨hal-02962274⟩