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- Title
Enantioselective Cross‐Exchange between C−I and C−C σ Bonds.
- Authors
Sun, Yu‐Li; Wang, Xing‐Ben; Sun, Feng‐Na; Chen, Qian‐Qian; Cao, Jian; Xu, Zheng; Xu, Li‐Wen
- Abstract
A palladium‐catalyzed enantioselective intramolecular σ‐bond cross‐exchange between C−I and C−C bonds is realized, providing chiral indanones bearing an alkyl iodide group and an all‐carbon quaternary stereocenter. Pd/TADDOL‐derived phosphoramidite is found to be an efficient catalytic system for both C−C bond cleavage and alkyl iodide reductive elimination. In addition to aryl iodides, aryl bromides can also be used for this transformation in the presence of KI. Density‐functional theory (DFT) calculation studies support the ring‐opening of cyclobutanones occuring through an oxidative addition/reductive elimination process involving PdIV species.
- Subjects
PALLADIUM catalysts; ENANTIOSELECTIVE catalysis; CARBON-carbon bonds; ALKYL iodide; DENSITY functional theory; CYCLOBUTANONES
- Publication
Angewandte Chemie, 2019, Vol 131, Issue 20, p6819
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.201902029