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Synthesis 2021; 53(03): 447-460
DOI: 10.1055/s-0040-1706055
DOI: 10.1055/s-0040-1706055
short review
Are Organozirconium Reagents Applicable in Current Organic Synthesis?
This work was supported by the Agentúra na Podporu Výskumu a Vývoja (Slovak Research and Development Agency) (Grant No. APVV-18-0242).
Abstract
The search for mild, user-friendly, easily accessible, and robust organometallic reagents is an important feature of organometallic chemistry. Ideally, new methodologies employing organometallics should be developed with respect to practical applications in syntheses of target compounds. In this short review, we investigate if organozirconium reagents can fulfill these criteria. Organozirconium compounds are typically generated via in situ hydrozirconation of alkenes or alkynes with the Schwartz reagent. Alkyl and alkenylzirconium reagents have proven to be convenient in conjugate additions, allylic substitutions, cross-coupling reactions, and additions to carbonyls or imines. Furthermore, the Schwartz reagent itself is a useful reducing agent for polar functional groups.
1 Introduction
2 Synthesis and Generation of the Schwartz Reagent
3 Structure and Properties of Cp2Zr(H)Cl
4 Reactivity of Organozirconium Reagents
4.1 Asymmetric Conjugate Addition
4.2 Asymmetric Allylic Alkylations
4.3 Desymmetrization Reactions
4.4 Cross-Coupling Reactions
4.5 1,2-Additions
5 Conclusions
Publication History
Received: 16 July 2020
Accepted after revision: 03 September 2020
Article published online:
01 October 2020
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