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- Title
Synthesis of Fulvene Vinyl Ethers by Gold Catalysis.
- Authors
Ahrens, Alexander; Schwarz, Julia; Lustosa, Danilo M.; Pourkaveh, Raheleh; Hoffmann, Marvin; Rominger, Frank; Rudolph, Matthias; Dreuw, Andreas; Hashmi, A. Stephen K.
- Abstract
Gold‐catalyzed cyclization of 1,5‐diynes with ketones as reagents and solvent provides diversely substituted vinyl ethers under mild conditions. The regioselectivity of such gold‐catalyzed cyclizations is usually controlled by the scaffold of the diyne. Herein, we report the first solvent‐controlled switching of regioselectivity from a 6‐endo‐dig‐ to 5‐endo‐dig‐cyclization in these transformations, providing fulvene derivatives. With respect to the functional‐group tolerance, aryl fluorides, chlorides, bromides, and ethers are tolerated. Furthermore, the mechanism and selectivity are put to scrutiny by experimental studies and a thermodynamic analysis of the product. Additionally, 6‐(vinyloxy)fulvenes are a hitherto unknown class of compounds. Their reactivity is briefly evaluated, to give insights into their potential applications.
- Subjects
VINYL ethers; CATALYSIS; FULVENES; KETONES; ETHERS; FLUORIDES; ARYL chlorides
- Publication
Chemistry - A European Journal, 2020, Vol 26, Issue 23, p5280
- ISSN
0947-6539
- Publication type
Academic Journal
- DOI
10.1002/chem.202000338