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Reactive trans-dimetallated alkenes from alkynes

Reductive anti-1,2-dimetallation of alkynes proceeds through the use of sodium dispersion as a reducing agent and an organomagnesium or organoaluminum halide as a reduction-resistant electrophile. The reaction stereoselectively generates trans-1,2-dimagnesio- or 1,2-dialuminoalkenes, which show useful reactivity.

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Fig. 1: Generation of trans-1,2-dimagnesioalkenes and trans-1,2-dialuminoalkenes.

References

  1. Juhász, K., Magyar, Á. & Hell, Z. Transition-metal-catalyzed cross-coupling reactions of Grignard reagents. Synthesis 53, 983–1002 (2021). A review article that presents the utility of Grignard reagents in modern organic synthesis.

    Article  Google Scholar 

  2. Levin, G., Jagur-Grodzinski, J. & Szwarc, M. Chemistry of radical anions and dianions of diphenylacetylene. J. Am. Chem. Soc. 92, 2268–2275 (1970). This paper reports the instability of 1,2-dimetallated species.

    Article  CAS  Google Scholar 

  3. Dange, D. et al. Acyclic 1,2-dimagnesioethanes/-ethene derived from magnesium(i) compounds: multipurpose reagents for organometallic synthesis. Chem. Sci. 10, 3208–3216 (2019). This paper reports an example of the synthesis of 1,2-dimetallated species starting from a highly elaborate inorganic precursor.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  4. Fukazawa, M., Takahashi, F., Nogi, K., Sasamori, T. & Yorimitsu, H. Reductive difunctionalization of aryl alkenes with sodium metal and reduction-resistant alkoxy-substituted electrophiles. Org. Lett. 22, 2303–2307 (2020). This paper reports the use of trialkoxyboranes as reduction-resistant electrophiles.

    Article  CAS  PubMed  Google Scholar 

Download references

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This is a summary of: Takahashi, F., Kurogi, T. & Yorimitsu, H. Synthesis of trans-1,2-dimetalloalkenes through reductive anti-dimagnesiation and dialumination of alkynes. Nat. Synth. https://doi.org/10.1038/s44160-022-00189-z (2022).

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Reactive trans-dimetallated alkenes from alkynes. Nat. Synth 2, 90–91 (2023). https://doi.org/10.1038/s44160-022-00190-6

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  • DOI: https://doi.org/10.1038/s44160-022-00190-6

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