Related Experiment Video
Updated: May 28, 2025

Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes
Published on: April 1, 2013
Synthesis of Phosphinylated Naphthalene Diimides and Radical Anions: A SeT-Mediated Route Circumvents the Use of
Rustam Tamim1, Poonam Saini1, Krishna Kumar M S1
1Supramolecular and Material Chemistry Lab, School of Physical Sciences, Jawaharlal Nehru University, New Delhi 110067, India.
Abstract:
Phosphinylation of π-scaffolds is of huge current interest; however, the ensuing C-P(O) bond formation necessitates catalyst, light, heat, etc. We report that electron-deficient halogenated naphthalene diimide (NDI) scaffolds can enable catalyst-free, room-temperature phosphinylation via a possible single-eT-mediated reaction. The arylphosphinylated NDIs show multielectron acceptor property, and LUMO of -4.24 eV, rendering the Ph2PO group equally potent as the electron-withdrawing C≡N group. Thus, in situ reduction can be propelled leading to radical anions and dianions.
Related Concept Videos
Preparation of Nitriles
Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions
Radical Substitution: Hydrogenolysis of Alkyl Halides with Tributyltin Hydride
The bonds formed in this reaction are stronger than the bonds broken, making it energetically favorable. The reaction follows a radical chain mechanism similar to radical halogenation...
Preparation of 1° Amines: Gabriel Synthesis
Strong bases like NaOH or KOH deprotonate the phthalimide to form the corresponding anion, which acts as a nucleophile. Further, the anion attacks an...
Radical Reactivity: Nucleophilic Radicals
Radical Reactivity: Intramolecular vs Intermolecular
![[DPEPhosbcpCu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2FCDNSource%2Fteasers%2F59739.jpg&w=3840&q=50)
