AI Article Synopsis
- The study focuses on an efficient method for converting carbonyl compounds, particularly ketones, into valuable alkenes using a nickel catalyst and hydrazine.
- This new approach offers advantages over traditional methods like the Shapiro reaction, including compatibility with various substrates and milder reaction conditions.
- The process yields environmentally friendly byproducts and demonstrates practical applicability through successful large-scale synthesis, highlighting its potential for pharmaceutical development.
Article Abstract
The direct conversion of naturally abundant carbonyl compounds provides a powerful platform for the efficient synthesis of valuable chemicals. In particular, the conversion of ketones to alkenes is a commonly encountered chemical transformation, often achieved via the multistep Shapiro reaction with tosylhydrazone and over stoichiometric organolithium or Grignard reagent. Herein, we report an earth abundant nickel-catalyzed alkenylation of naturally abundant methylene ketones to afford a wide range of alkene derivatives, mediated by hydrazine. The protocol features a broad substrate scope (including alkyl ketones, aryl ketones, and aldehydes), good functional group compatibility, mild reaction conditions, water tolerance, and only environmentally friendly N, H, and HO as theoretical byproducts. Moreover, gram-scale synthesis with good yield and generation of pharmaceutical intermediates highlighted its practical applicability.
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| http://www.ncbi.nlm.nih.gov/pmc/articles/PMC9400169 | PMC |
| http://dx.doi.org/10.1021/jacsau.2c00320 | DOI Listing |
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