cs401164z_si_001.pdf (1.32 MB)
Palladium-Catalyzed Stille-Type Coupling of N‑Acyl Iminium Ions with Distannanes: A Multicomponent Synthesis of α‑Amidostannanes
journal contribution
posted on 2015-12-17, 00:56 authored by Boran Xu, Bruce A. ArndtsenThe
palladium-catalyzed three-component coupling of imines, acid chlorides,
and hexabutyldistannane is described. This results in the synthesis
of various α-amidostannanes in good yields, without the use
of strong nucleophilic organometallic reagents. The reaction is believed
to proceed via a Stille-type cross coupling of an in situ-generated N-acyl iminium salt with Bu3SnSnBu3 and reaches completion within 1 h at ambient temperature
using simple, unligated Pd2dba3 as a catalyst.
Combining the formation of α-amidostannanes with lithiation
and carboxylation allows the overall synthesis of amino acid derivatives
in two steps from imines, acid chlorides, and CO2.