C-H functionalization of amines with aryl halides by nickel-photoredox catalysis.

Chem Sci 2016 Dec 28;7(12):7002-7006. Epub 2016 Jul 28.

Department of Chemistry, Princeton University, Princeton, NJ 08544, USA.

We describe the functionalization of α-amino C-H bonds with aryl halides using a combination of nickel and photoredox catalysis. This direct C-H, C-X coupling uses inexpensive and readily available starting materials to generate benzylic amines, an important class of bioactive molecules. Mechanistically, this method features the direct arylation of α-amino radicals mediated by a nickel catalyst. This reactivity is demonstrated for a range of aryl halides and -aryl amines, with orthogonal scope to existing C-H activation and photoredox methodologies. We also report reactions with several complex aryl halides, demonstrating the potential utility of this approach in late-stage functionalization.

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http://dx.doi.org/10.1039/C6SC02815BDOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC5207500PMC
December 2016
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References

(Supplied by CrossRef)

Godula et al.
Science 2006

Yamaguchi et al.
Angew. Chem., Int. Ed. 2012

Wencel-Delord et al.
Nat. Chem. 2013

Jazzar et al.
Chem.–Eur. J. 2010

Baudoin et al.
Chem. Soc. Rev. 2011

Ackermann et al.
Chem. Rev. 2011

Daugulis et al.
Acc. Chem. Res. 2009

Lyons et al.
Chem. Rev. 2010

Chen et al.
Angew. Chem., Int. Ed. 2009

Kakiuchi et al.
Synthesis 2008

Bellina et al.
Chem. Rev. 2010

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