Article Synopsis
- Cyclobutadiene is a highly reactive antiaromatic hydrocarbon that has been a topic of interest for chemists for over 60 years, but its limited use in synthesis is due to its complicated and hazardous preparation.
- Researchers have developed a scalable, metal-free cyclobutadiene reagent called diethyldiazabicyclohexene dicarboxylate.
- This new reagent facilitates a range of reactions, including a [4 + 2] cycloaddition with electron-deficient alkenes and a three-step synthesis of dipiperamide G, showcasing its versatility in product derivatizations like bromocyclobutadiene.
Video Abstracts
Category Ranking
98%
Total Visits
921
Avg Visit Duration
2 minutes
Citations
20
Article Abstract
Cyclobutadiene is a highly reactive antiaromatic hydrocarbon that has fascinated chemists for over 60 years. However, its preparation and uses in chemical synthesis are sparing, in part due to its lengthy synthesis that generates hazardous byproducts including excess heavy metals. Herein, we report a scalable, metal-free cyclobutadiene reagent, diethyldiazabicyclohexene dicarboxylate, and explore its intermolecular [4 + 2] cycloaddition with various electron-deficient alkenes. We also demonstrate its utility in a three-step synthesis of dipiperamide G and a diverse array of product derivatizations including bromocyclobutadiene.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1021/jacs.3c01591 | DOI Listing |
Publication Analysis
Top Keywords
metal-free cyclobutadiene
8
cyclobutadiene reagent
8
reagent intermolecular
4
intermolecular cycloadditions
4
cycloadditions cyclobutadiene
4
cyclobutadiene highly
4
highly reactive
4
reactive antiaromatic
4
antiaromatic hydrocarbon
4
hydrocarbon fascinated
4