Skip to Content
Merck
  • Diamine-free lithiation-trapping of N-Boc heterocycles using s-BuLi in THF.

Diamine-free lithiation-trapping of N-Boc heterocycles using s-BuLi in THF.

Organic letters (2010-08-20)
Graeme Barker, Peter O'Brien, Kevin R Campos
ABSTRACT

A diamine-free protocol for the s-BuLi-mediated lithiation-trapping of N-Boc heterocycles has been developed. In the optimized procedure, lithiation is accomplished using s-BuLi in THF at -30 °C for only 5 or 10 min. Subsequent electrophilic trapping or transmetalation-Negishi coupling delivered a range of functionalized pyrrolidines, imidazolidines, and piperazines in 43-83% yield.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
n-Butyllithium solution, 2.0 M in cyclohexane