Aminium cation-radical catalysed selective hydration of (E)-aryl enynes

Giel, Marie-Claire, Barrow, Andrew S, Smedley, Christopher J, Lewis, William, Moses, John E (June 2021) Aminium cation-radical catalysed selective hydration of (E)-aryl enynes. Chemical Communications. ISSN 1359-7345

DOI: 10.1039/d1cc02257a


The hydration of carbon-carbon triple bonds is an important and atom economic synthetic transformation. Herein, we report a mild and selective method for the catalytic Markovnikov hydration of (E)-aryl enynes to the corresponding enones, mediated through the bench-stable aminium salt, tris(4-bromophenyl)ammoniumyl hexachloroantimonate (TBPA). The chemoselective and diastereoselective method proceeds under neutral metal-free conditions, delivering excellent product yields from terminal and internal alkyne units. The synthesis of biologically important (E)-3-styrylisocoumarins, including a formal synthesis of the natural product achlisocoumarin III, demonstrates the utility of this novel transformation.

Item Type: Paper
Subjects: chemistry
CSHL Authors:
Communities: CSHL Cancer Center Program
CSHL Cancer Center Program > Gene Regulation and Inheritance Program
CSHL labs > Moses lab
SWORD Depositor: CSHL Elements
Depositing User: CSHL Elements
Date: 22 June 2021
Date Deposited: 24 Jun 2021 15:22
Last Modified: 13 Feb 2024 16:55
PMCID: PMC8895482
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