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. 2011 Apr 1;13(7):1738-41.
doi: 10.1021/ol2002607. Epub 2011 Feb 25.

Gold-catalyzed nitrene transfer to activated alkynes: formation of α,β-unsaturated amidines

Chaoqun Li  1 , Liming Zhang
Affiliations

Gold-catalyzed nitrene transfer to activated alkynes: formation of α,β-unsaturated amidines

Chaoqun Li et al. Org Lett. .

Abstract

A gold-catalyzed intermolecular nitrene transfer to alkynes was developed for the first time, revealing a new mode of nitrene transfer and providing a novel access to versatile α-imino metal carbenes. Various mild nitrene-transfer reagents were examined, and iminopyridium ylides especially those based on 3,5-dichloropyridine proved be highly effective. With activated alkynes such as N-alkynyloxazolidinones as substrates, α,β-unsaturated amidines were formed in mostly good yields.

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Figures

Figure 1
Figure 1
Selected nitrene-transfer reagents (NTR)
Figure 1
Figure 1
ORTEP drawing of E-14j.
Scheme 1
Scheme 1
Gold-catalyzed oxygen/nitrene transfer to alkyne: concept
Scheme 2
Scheme 2
Rationale for the formation of the E-C-N double bond
See this image and copyright information in PMC

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References

    1. Li C-W, Pati K, Lin G-Y, Sohel SMA, Hung H-H, Liu R-S. Angew Chem, Int Ed. 2010 doi: 10.1002/anie.201004647. - DOI - PubMed
    2. Cui L, Zhang G, Peng Y, Zhang L. Org Lett. 2009;11:1225–1228. - PubMed
    3. Cui L, Ye L, Zhang L. Chem Commun. 2010;46:3351–3353. - PMC - PubMed
    1. Shapiro ND, Toste FD. J Am Chem Soc. 2007;129:4160–4161. - PubMed
    2. Li G, Zhang L. Angew Chem, Int Ed. 2007;46:5156–5159. - PubMed
    3. Davies PW, Albrecht SJC. Angew Chem, Int Ed. 2009;48:8372–8375. - PubMed
    4. Davies PW. 2010;82:1537–1544. - PubMed
    1. Cui L, Peng Y, Zhang L. J Am Chem Soc. 2009;131:8394–8395. - PubMed
    1. Yeom HS, Lee Y, Lee JE, Shin S. Org Biomol Chem. 2009;7:4744–4752. - PubMed
    2. Yeom HS, Lee Y, Jeong J, So E, Hwang S, Lee JE, Lee SS, Shin S. Angew Chem, Int Ed. 2010;49:1611–1614. - PubMed
    3. Yeom HS, Lee JE, Shin S. Angew Chem, Int Ed. 2008;47:7040–7043. - PubMed
    1. Lin GY, Li CW, Hung SH, Liu RS. Org Lett. 2008;10:5059–5062. - PubMed
    2. Li CW, Lin GY, Liu RS. Chem Eur J. 2010;16:5803–5811. - PubMed
    3. Hashmi ASK, Buehrle M, Salathe R, Bats JW. Adv Synth Catal. 2008;350:2059–2064.

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