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Synfacts 2013; 9(4): 0421
DOI: 10.1055/s-0032-1318384
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart · New York

Ni-Catalyzed Suzuki Arylation of Unactivated Tertiary Alkyl Halides

Contributor(s):
Paul Knochel
,
Christoph Sämann
Zultanski SL, Fu GC * Massachusetts Institute of Technology, Cambridge and California Institute of Technology, Pasadena, USA
Nickel-Catalyzed Carbon-Carbon Bond-Forming Reactions of Unactivated Tertiary Alkyl Halides: Suzuki Arylations.

J. Am. Chem. Soc. 2013;
135: 624-627
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Further Information

Publication History

Publication Date:
15 March 2013 (online)

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Key words

Suzuki cross-coupling - tertiary alkyl halides - nickel

Significance

The first nickel-catalyzed Suzuki cross-coupling reaction of unactivated tertiary alkyl halides has been disclosed. Both the nickel catalyst as well as the bipyridine ligand are commercially available. The desired products have been obtained in excellent yields.


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Comment

The described reaction is very versatile since the synthesis of the all-carbon quaternary carbon centers does not suffer from isomerization of the alkyl group. Preliminary mechanistic studies indicate the generation of a radical intermediate along the reaction pathway.


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