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Synthesis 2024; 56(21): 3307-3313
DOI: 10.1055/a-2326-6416
DOI: 10.1055/a-2326-6416
paper
Special Issue PSRC-10 (10th Pacific Symposium on Radical Chemistry)
Sodium-Mediated Reductive anti-Dimagnesiation of Diarylacetylenes with Magnesium Bromide
This work was supported by Japan Science and Technology Agency (JST) Core Research for Evolutional Science and Technology (CREST, Grant Number JPMJCR19R4) as well as Japan Society for the Promotion of Science (JSPS) KAKENHI Grant Numbers JP19H00895 and JP24H02208 to H.Y.
This paper is dedicated to Professor Dr. Thorsten Bach on his 60th birthday.
Abstract
Diarylacetylenes undergo anti-dimagnesiation using magnesium bromide and sodium dispersion to afford (E)-1,2-dimagnesioalkenes. This dimagnesiation utilizes simple magnesium bromide as a reduction-resistant electrophile, contrasting with the previously reported dimagnesiation using tricky organomagnesium halides. The resulting vicinal double Grignard reagents react with various electrophiles to yield multisubstituted alkenes stereoselectively.
Key words
organomagnesium compounds - sodium dispersion - alkynes - electron transfer - multisubstituted alkenesSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-2326-6416.
- Supporting Information
Publication History
Received: 28 April 2024
Accepted after revision: 14 May 2024
Accepted Manuscript online:
14 May 2024
Article published online:
28 May 2024
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Selective examples of reductive transformations using Na dispersion:
Our examples of reductive transformations using Na dispersion: