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FeTPPCl/FeCl 3 Co-Catalyzed One-Pot Green Synthesis of α-Diaryl-β-alkynol Derivatives via Propargylic Carbocation Chemistry.

Authors :
Song L
Ni D
Han W
Tang J
Yang F
Liu S
Source :
The Journal of organic chemistry [J Org Chem] 2021 Jul 16; Vol. 86 (14), pp. 9306-9316. Date of Electronic Publication: 2021 Jul 06.
Publication Year :
2021

Abstract

A green and highly efficient one-pot method for α-diaryl-β-alkynol derivatives in water at room temperature was developed using the cocatalysis of a Lewis acid and meso-tetraphenylporphyrin iron(III) chloride (FeTPPCl). The unprecedented transformation was promoted by a modulation of the charge properties of propargylic carbocation chemistry and the use of an in situ-generated oxonium ylide as a matching nucleophile. The reaction was performed in water at room temperature with a highly step-economic manipulation in good to excellent yields and with a broad substrate scope. Water also acts as the third reactant for the one-pot transformation. Notably, the FeTPPCl catalyst can be directly reused four times with a slight discount in yields.

Details

Language :
English
ISSN :
1520-6904
Volume :
86
Issue :
14
Database :
MEDLINE
Journal :
The Journal of organic chemistry
Publication Type :
Academic Journal
Accession number :
34228462
Full Text :
https://doi.org/10.1021/acs.joc.1c00474