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Synfacts 2014; 10(9): 0966
DOI: 10.1055/s-0034-1378963
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart · New York

Cobalt-Catalyzed Migratory Arylzincation

Contributor(s):
Paul Knochel
,
Thomas Klatt
Tan B.-H, Yoshikai N * Nanyang Technological University, Singapore, Singapore
Cobalt-Catalyzed Addition of Arylzinc Reagents to Norbornene Derivatives through 1,4-Cobalt Migration.

Org. Lett. 2014;
16: 3392-3395
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Publication History

Publication Date:
18 August 2014 (online)

 
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Key words

cobalt - zinc - 1,4-migration

Significance

Tan and Yoshikai describe a cobalt–diphosphine-catalyzed addition reaction of an arylzinc reagent to a norbornene derivative. The reaction involves the insertion of the norbornene into an arylcobalt species, alkyl-to-aryl 1,4-cobalt migration, and transmetalation between the resulting o-(2-exo-norbornyl)arylcobalt species and the arylzinc reagent.


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Comment

The authors show that the resulting o-(2-exo-norbornyl)arylzinc species undergo reactions with common organic electrophiles under copper or palladium catalysis; for example allylation, acylation, and cross-coupling reactions.


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