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Air-stable zirconocene bis(perfluorobutanesulfonate) as a highly efficient catalyst for synthesis of α-aminophosphonates via Kabachnik–Fields reaction under solvent-free condition

Paper ID Volume ID Publish Year Pages File Format Full-Text
50438 46794 2014 4 PDF Available
Title
Air-stable zirconocene bis(perfluorobutanesulfonate) as a highly efficient catalyst for synthesis of α-aminophosphonates via Kabachnik–Fields reaction under solvent-free condition
Abstract

•A general and mild protocol for the synthesis of α-aminophosphonates•Catalytic amount of Cp2Zr(OSO2C4F9)2·2H2O exhibited higher catalytic activity.•The good-to-excellent yields were obtained under solvent-free condition.•Catalyst can be reused without significant loss of activity in a test of five cycles.•A plausible mechanistic approach has also been proposed.

Zirconocene bis(perfluorobutanesulfonate) [Cp2Zr(OSO2C4F9)2·2H2O] was successfully synthesized by treatment of Cp2ZrCl2 with C4F9SO3Ag, and was found to have the nature of air-stability, water tolerance, high thermal stability and strong Lewis acidity. This complex showed high catalytic efficiency for the synthesis of α-aminophosphonates via Kabachnik–Fields reaction of aldehydes/ketones, amines and diethyl phosphite under mild and solvent-free conditions. Furthermore, it can be reused without loss of activity in a test of five cycles. Compared with our previously reported complex of Cp2Zr(OSO2C8F17)2·3H2O·THF, this complex showed better catalytic activity.

Graphical abstractA general mild and efficient, one-pot, solvent-free protocol for the synthesis of α-aminophosphonates has been developed via the Kabachnik–Fields reaction of aldehydes/ketones, amines and diethyl phosphite using recyclable catalyst zirconocene bis(perfluorobutanesulfonate). On account of its stability as well as storability, this catalyst should find a broad range of utility.Figure optionsDownload full-size imageDownload as PowerPoint slide

Keywords
Zirconocene; Perfluorobutanesulfonate; Lewis acid; Kabachnik–Fields reaction; α-Aminophosphonates
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Air-stable zirconocene bis(perfluorobutanesulfonate) as a highly efficient catalyst for synthesis of α-aminophosphonates via Kabachnik–Fields reaction under solvent-free condition
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Publisher
Database: Elsevier - ScienceDirect
Journal: Catalysis Communications - Volume 43, 5 January 2014, Pages 184–187
Authors
, , , , , , , ,
Subjects
Physical Sciences and Engineering Chemical Engineering Catalysis
Get Full-Text Now
Don't Miss Today's Special Offer
Price was $35.95
You save - $31
Price after discount Only $4.95
100% Money Back Guarantee
Full-text PDF Download
Online Support
Any Questions? feel free to contact us