Next Article in Journal
Studies on the Inclusion Complexes of Daidzein with β-Cyclodextrin and Derivatives
Next Article in Special Issue
Recent Advances in Organocatalyzed Domino C–C Bond-Forming Reactions
Previous Article in Journal
A Seed Expansion Graph Clustering Method for Protein Complexes Detection in Protein Interaction Networks
Previous Article in Special Issue
Non-Covalent Organocatalyzed Domino Reactions Involving Oxindoles: Recent Advances
Article Menu
Issue 12 (December) cover image

Export Article

Open AccessArticle
Molecules 2017, 22(12), 2181; doi:10.3390/molecules22122181

Novel Chiral Bis-Phosphoramides as Organocatalysts for Tetrachlorosilane-Mediated Reactions

Dipartimento di Chimica, Università Degli Studi di Milano, via Golgi 19, 20133 Milan, Italy
*
Authors to whom correspondence should be addressed.
Received: 5 October 2017 / Revised: 30 November 2017 / Accepted: 5 December 2017 / Published: 8 December 2017
(This article belongs to the Collection Recent Advances in Organocatalysis)
View Full-Text   |   Download PDF [1688 KB, uploaded 8 December 2017]   |  

Abstract

The formation of novel chiral bidentate phosphoroamides structures able to promote Lewis base-catalyzed Lewis acid-mediated reactions was investigated. Two different classes of phosphoroamides were synthetized: the first class presents a phthalic acid/primary diamine moiety, designed with the aim to perform a self-assembly recognition process through hydrogen bonds; the second one is characterized by the presence of two phosphoroamides as side arms connected to a central pyridine unit, able to chelate SiCl4 in a 2:1 adduct. These species were tested as organocatalysts in the stereoselective allylation of benzaldehyde and a few other aromatic aldehydes with allyl tributyltin in the presence of SiCl4 with good results. NMR studies confirm that only pyridine-based phosphoroamides effectively coordinate tetrachlorosilane and may lead to the generation of a self-assembled entity that would act as a promoter of the reaction. Although further work is necessary to clarify and confirm the formation of the hypothesized adduct, the study lays the foundation for the design and the synthesis of chiral supramolecular organocatalysts. View Full-Text
Keywords: phosphoroamides; metal-free catalysis; hypervalent silicon; allylation; self-assembly phosphoroamides; metal-free catalysis; hypervalent silicon; allylation; self-assembly
Figures

Figure 1

This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

Supplementary material

Scifeed alert for new publications

Never miss any articles matching your research from any publisher
  • Get alerts for new papers matching your research
  • Find out the new papers from selected authors
  • Updated daily for 49'000+ journals and 6000+ publishers
  • Define your Scifeed now

SciFeed Share & Cite This Article

MDPI and ACS Style

Rossi, S.; Ziliani, M.; Annunziata, R.; Benaglia, M. Novel Chiral Bis-Phosphoramides as Organocatalysts for Tetrachlorosilane-Mediated Reactions. Molecules 2017, 22, 2181.

Show more citation formats Show less citations formats

Note that from the first issue of 2016, MDPI journals use article numbers instead of page numbers. See further details here.

Related Articles

Article Metrics

Article Access Statistics

1

Comments

[Return to top]
Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert
Back to Top