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. 2010 Jun 18;12(12):2848-51.
doi: 10.1021/ol1009575.

Pd(II)-catalyzed oxidative 1,1-diarylation of terminal olefins

Erik W Werner  1 , Kaveri B Urkalan, Matthew S Sigman
Affiliations

Pd(II)-catalyzed oxidative 1,1-diarylation of terminal olefins

Erik W Werner et al. Org Lett. .

Abstract

Evaluation of the scope of a Pd(II)-catalyzed oxidative 1,1-diarylation reaction of terminal olefins using aryl stannanes is reported. The reaction is shown to be tolerant of functionality commonly encountered in organic synthesis; however, the reaction outcome was found to be dependent on the nature of the aryl stannane used. A mechanistic rationale for the observation of this influence is provided.

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Figures

Figure 1
Figure 1
Hammett plot
Scheme 1
Scheme 1
Diarylation of styrenes
Scheme 2
Scheme 2
1,1-Diarylation of nonene
See this image and copyright information in PMC

References

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    1. For examples of hydrofunctionalization using a similar strategy, see: Gligorich KM, Schultz MJ, Sigman MS. J. Am. Chem. Soc. 2006;128:2794–2795. Gligorich KM, Cummings SA, Sigman MS. J. Am. Chem. Soc. 2007;129:14193–14195. Podhajsky SM, Sigman MS. Organometallics. 2007;26:5680–5686. Iwai Y, Gligorich KM, Sigman MS. Angew. Chem., Int. Ed. 2008;47:3219–3222. Urkalan KB, Sigman MS. J. Am. Chem. Soc. 2009;131:18042–18043.

    1. For examples of palladium-catalyzed diamination reactions see: Bar GLJ, Lloyd-Jones GC, Booker-Milburn KI. J. Am. Chem. Soc. 2005;127:7308–7309. Du H, Zhao B, Shi Y. J. Am. Chem. Soc. 2007;129:762–763. Du H, Yuan W, Zhao B, Shi Y. J. Am Chem. Soc. 2007;129:11688–11689. Xu L, Shi Y. J. Org. Chem. 2008;73:749–751. Du H, Yuan W, Zhao B, Shi Y. J. Am. Chem. Soc. 2007;129:7496–7497. Du H, Zhao B, Shi Y. J. Am. Chem. Soc. 2008;130:8590–8591.

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