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

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

doi:10.1021/ol1017799

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

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

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72 Citations (Scopus)

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.

Original language	English
Pages (from-to)	4176-4179
Number of pages	4
Journal	Organic Letters
Volume	12
Issue number	18
Early online date	18 Aug 2010
DOIs	https://doi.org/10.1021/ol1017799
Publication status	Published - 17 Sept 2010

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title = "Diamine-Free Lithiation−Trapping of N-Boc Heterocycles using s-BuLi in THF",

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.",

author = "Graeme Barker and Peter O'Brien and Campos, \{Kevin R.\}",

year = "2010",

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doi = "10.1021/ol1017799",

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AU - O'Brien, Peter

AU - Campos, Kevin R.

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N2 - 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.

AB - 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.

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DO - 10.1021/ol1017799

M3 - Article

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JO - Organic Letters

JF - Organic Letters

IS - 18

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

Abstract

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