Generation of Photoinduced Phenalenyl‐Based Radicals: Towards Designing Reductive C−C Coupling Catalysis

Author:

Datta Paramita1ORCID,Goswami Tanmay2,Kandoth Noufal1,Banik Ananya1,Ahmed Jasimuddin1,Bhaskaran Athul Santha3,Saha Ramchandra2,Kuniyil Rositha3,Ghosh Hirendra N.24ORCID,Mandal Swadhin K.1ORCID

Affiliation:

1. Department of Chemical Sciences Indian Institute of Science Education and Research Kolkata Mohanpur 741246 Nadia India

2. Energy and Environmental Unit Institute of Nano Science and Technology (INST) Mohali, Sector-81 Punjab 140306 India

3. Department of Chemistry Indian Institute of Technology Palakkad (IIT PKD) Palakkad 678557 Kerala India

4. Radiation and Photochemistry Division Bhabha Atomic Research Centre Mumbai 400085 India

Abstract

AbstractOrganic photoredox catalysis is a versatile tool for accessing a wide range of synthetic transformations. Towards the development of a new class of organophotoredox catalysts, we have employed phenalenyl, an odd alternant hydrocarbon (OAH), for reductive C−C coupling reactions. Phenalenyl can adopt a stable open‐shell state (radical), using its non‐bonding molecular orbital. To date, chemically induced phenalenyl‐based radicals have been extensively explored in designing various intriguing organic materials and recently towards electron transfer catalysis. However, the photochemical generation of phenalenyl‐based radicals is rare. In this work, we report the photoinduced generation of phenalenyl‐based radicals with detailed mechanistic studies such as steady‐state absorption, time‐resolved transient absorption spectroscopy, and in‐situ absorption kinetic experiments to authenticate the generation of photo‐induced phenalenyl radicals. In addition, we present results demonstrating that this novel catalytic species can be applied to reductive pinacol coupling catalysis and reductive alkylation of terminal alkynes.

Publisher

Wiley

Subject

Organic Chemistry,Physical and Theoretical Chemistry,Analytical Chemistry

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