Synlett 2019; 30(16): 1843-1849
DOI: 10.1055/s-0037-1611843
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© Georg Thieme Verlag Stuttgart · New York

Organocerium: A New Contender for Halogen–Metal Exchanges

Arif Music
,
Dorian Didier*
Ludwig-Maximilians-Universität, Department of Chemistry and Pharmacy, Butenandtstraße 5–13, 81377 Munich, Germany   Email: dorian.didier@cup.uni-muenchen.de
› Author Affiliations
The authors are grateful to the Fonds der Chemischen Industrie and the Ludwig-Maximilians Universität for financial support.
Further Information

Publication History

Received: 05 April 2019

Accepted after revision: 07 May 2019

Publication Date:
03 June 2019 (online)

Abstract

In the context of our current research on dependable and sustainable methods for C–C bond-forming reactions, we have recently developed new strategies to generate organocerium reagents through simple bromide–cerium exchanges. n-Bu3Ce enabled a fast and general access to functionalized triaryl- and alkenyl cerium species from the corresponding aryl- and alkenyl bromides. A broad range of these new organocerium species was engaged in Zweifel’s olefination, allowing for the synthesis of widely substituted alkene derivatives in a stereospecific way. Herein, we place the formation of organocerium species in the context of known organometallic reagents (Li, Mg, Zn, Cu, Ca, La, and Sm) generated through halogen–metal exchange reactions and their application in further transformations.

 
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