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- Title
Forging Medium Rings via I(I)/I(III)‐Catalyzed Diene Carbofunctionalization.
- Authors
Yu, You‐Jie; Häfliger, Joel; Wang, Zi‐Xuan; Daniliuc, Constantin G.; Gilmour, Ryan
- Abstract
A main‐group catalysis‐based strategy to access 8‐membered carbocycles via the direct carbofunctionalization of 2‐phenethyl‐substituted 1,3‐dienes is disclosed. Through the intervention of an I(I)/I(III) catalysis cycle, the synthesis of densely functionalized, fluorinated benzocyclooctenes can be achieved in an operationally simple manner. Modulating the oxidation/activation regime, and the external nucleophile, the process has been extended to unify the challenging cyclization with formation of allylic C−O, C−N, and C−C bonds (>30 examples). Derivatization of the product benzocyclooctenes is demonstrated together with X‐ray conformational analysis, preliminary validation of enantioselective catalysis and a scalable resolution protocol.
- Subjects
ENANTIOSELECTIVE catalysis; DERIVATIZATION; RING formation (Chemistry); CATALYSIS; CONFORMATIONAL analysis
- Publication
Angewandte Chemie, 2023, Vol 135, Issue 38, p1
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.202309789