Abstract We report the oxidative dimerization reaction of siloxydienes derived from simple enones that creates a new gamma‐gamma (γ‐γ) C−C bond using catalytic iron and benzoyl peroxide as the terminal oxidant in acetonitrile solvent at ambient temperature. The reaction shows a broad substrate scope including cyclic and acyclic siloxydienes derived from ketones, aldehydes, and esters, which are converted to 1,8‐dicarbonyl compounds under mild catalytic reaction conditions in 19–89 % yield across 30 examples. The method is suitable for the coupling of sterically demanding carbon centers, including the formation of vicinal quaternary centers. Conceptually, the dienol ether serves as a precursor to a conjugated radical cation, which undergoes highly site selective γ‐dimerization reactions. The γ‐γ dimerization strategy is applied to the synthesis of a bioactive analogue of honokiol.
more »
« less
Flickering gamma-ray flashes, the missing link between gamma glows and TGFs
- PAR ID:
- 10582676
- Author(s) / Creator(s):
- ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; more »
- Publisher / Repository:
- Nature
- Date Published:
- Journal Name:
- Nature
- Volume:
- 634
- Issue:
- 8032
- ISSN:
- 0028-0836
- Page Range / eLocation ID:
- 53 to 56
- Format(s):
- Medium: X
- Sponsoring Org:
- National Science Foundation
An official website of the United States government

