Diamine-Free Lithiation−Trapping of N-Boc Heterocycles using s-BuLi in THF

Graeme Barker, Peter O'Brien, Kevin R. Campos

Research output: Contribution to journalArticlepeer-review

70 Citations (Scopus)


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.
Original languageEnglish
Pages (from-to)4176-4179
Number of pages4
JournalOrganic Letters
Issue number18
Early online date18 Aug 2010
Publication statusPublished - 17 Sept 2010


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