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. 2008;47(43):8224-7.
doi: 10.1002/anie.200803184.

A palladium-catalyzed dehydrogenative diamination of terminal olefins

Bin Wang  1 , Haifeng Du, Yian Shi
Affiliations

A palladium-catalyzed dehydrogenative diamination of terminal olefins

Bin Wang et al. Angew Chem Int Ed Engl. 2008.
No abstract available

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Figures

Figure 1
Figure 1
The X-ray structure of compound 5f
Scheme 1
Scheme 1
Scheme 2
Scheme 2
Scheme 3
Scheme 3
Scheme 4
Scheme 4
A proposed catalytic cycle for diamination
Scheme 5
Scheme 5
Scheme 6
Scheme 6
See this image and copyright information in PMC

References

    1. For leading reviews, see: Lucet D, Gall TL, Mioskowski C. Angew. Chem. Int. Ed. 1998;37:2580.Mortensen MS, O'Doherty GA. Chemtracts: Organic Chemistry. 2005;18:555.Kotti SRSS, Timmons C, Li G. Chem. Biol. Drug. Des. 2006;67:101.

    1. For examples of metal-mediated diaminations, see: Co: Becker PN, White MA, Bergman RG. J. Am. Chem. Soc. 1980;102:5676. Hg: Barluenga J, Alonso-Cires L, Asensio G. Synthesis. 1979:962. Mn: Fristad WE, Brandvold TA, Peterson JR, Thompson SR. J. Org. Chem. 1985;50:3647. Os: Chong AO, Oshima K, Sharpless KB. J. Am. Chem. Soc. 1977;99:3420.Muñiz K. Eur. J. Org. Chem. 2004:2243.Muñiz K, Nieger M. Synlett. 2003:211.Muñiz K, Nieger M. Chem. Commun. 2005:2729. Pd: Bäckvall J-E. Tetrahedron Lett. 1978:163. Tl: Aranda VG, Barluenga J, Aznar F. Synthesis. 1974:504.

    1. For recent Cu(II)-mediated intramolecular diamination, see: Zabawa TP, Kasi D, Chemler SR. J. Am. Chem. Soc. 2005;127:11250.Zabawa TP, Chemler SR. Org. Lett. 2007;9:2035.

    1. For Rh(II), Fe(III)-catalyzed diamination with TsNCl2, see: Li G, Wei H-X, Kim SH, Carducci MD. Angew. Chem. Int. Ed. 2001;40:4277.Wei H-X, Kim SH, Li G. J. Org. Chem. 2002;67:4777.

    1. For a recent Pd(II)-catalyzed intermolecular diamination of conjugated dienes, see: Bar GLJ, Lloyd-Jones GC, Booker-Milburn KI. J. Am. Chem. Soc. 2005;127:7308.

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