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Synfacts 2016; 12(2): 0179
DOI: 10.1055/s-0035-1561147
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart · New York

Photoredox-Generated α-Amino Radicals Used in (Hetero)Arylation

Rezensent(en):
Paul Knochel
,
Sarah Fernandez
El Khatib M, Serafim RA. M, Molander GA * University of Pennsylvania, USA and University of São Paulo, Brazil
α-Arylation/Heteroarylation of Chiral α-Aminomethyltrifluoroborates by Synergistic Iridium Photoredox/Nickel Cross-Coupling Catalysis.

Angew. Chem. Int. Ed. 2016;
55: 254-258
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Publikationsverlauf

Publikationsdatum:
19. Januar 2016 (online)

 
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Key words

iridium - nickel - photochemistry - amino acids

Significance

Molander and co-workers report the arylation of chiral α-aminomethyltrifluoroborates by a synergistic dual catalysis strategy using iridium photoredox and nickel cross-coupling. α-Amino radical generation from the chiral N-trifluoroboratomethyl salt, followed by arylation, leads to enantiopure benzylic amines in high yields.


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Comment

This new Csp3–Csp3 bond-formation process uses abundant and inexpensive amino acids, and also has the advantage of the stability and storability of its reagents. Moreover, the reactions proceed at room temperature, under mild conditions.


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