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. 2013 Jan 28;52(5):1371-3.
doi: 10.1002/anie.201209338. Epub 2013 Jan 7.

Versatile reactivity of rhodium-iminocarbenes derived from N-sulfonyl triazoles

Anton V Gulevich  1 , Vladimir Gevorgyan
Affiliations

Versatile reactivity of rhodium-iminocarbenes derived from N-sulfonyl triazoles

Anton V Gulevich et al. Angew Chem Int Ed Engl. .
No abstract available

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Figures

Scheme 1
Scheme 1
Use of N-sulfonyl triazole to form Rh–iminocarbene.
Scheme 2
Scheme 2
The RhII-catalyzed rearrangement of triazolyl alcohols. Conditions A (Miura and Murakami[10]): CHCl3, 140°C, microwave, 15 min. Conditions B (Fokin[11]): CHCl3, 70°C, 5–60 min. Oct=octanoate, Ts=4-toluenesulfonyl.
See this image and copyright information in PMC

References

    1. For selected reviews on the reactivity of Rh carbenoids, see: Timmons DJ, Doyle MP. J. Organomet. Chem. 2001;617–618:98–104. Davies HML, Manning JR. Nature. 2008;451:417–424. Evans PA, editor. Modern Rhodium Catalyzed Organic Reactions. Weinheim: Wiley-VCH; 2005.

    1. See, for example: Gilchrist TL, Gymer GE. Adv. Heterocycl. Chem. 1974;16:33.

    1. For earlier reports on the ring-opening of N-sulfonyl 1,2,3-triazoles, see: Harmon RE, Stanley F, Gupta SK, Johnson J. J. Org. Chem. 1970;35:3444–3448. Himbert G, Regitz M. Chem. Ber. 1972;105:2963–2974. Himbert G, Regitz M. Synthesis. 1972:571–573.

    1. Horneff T, Chuprakov S, Chernyak N, Gevorgyan V, Fokin VV. J. Am. Chem. Soc. 2008;130:14972–14974. - PMC - PubMed
    1. Chuprakov S, Kwok SW, Zhang L, Lercher L, Fokin VV. J. Am. Chem. Soc. 2009;131:18034–18035. - PMC - PubMed
    2. Grimster N, Zhang L, Fokin VV. J. Am. Chem. Soc. 2010;132:2510–2511. - PMC - PubMed

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