Research

Chemical Sciences

Title :

Electrochemical Gold Catalysis: Discovering Methods for 1,2-Difunctionalization of C-C Multiple Bonds

Area of research :

Chemical Sciences

Principal Investigator :

Dr. Nitin T. Patil, Indian Institute Of Science Education And Research (IISER) Bhopal, Madhya Pradesh

Timeline Start Year :

2022

Timeline End Year :

2025

Contact info :

Equipments :

Details

Executive Summary :

Owing to the inherent carbophilic activation property, gold has emerged as the best catalyst for the functionalization of C-C multiple bonds; however, in the majority of the cases, the scope of such transformations has remained confined to afford monofunctionalized products. In this context, achieving gold-catalyzed 1,2-difunctionalization of C-C multiple bonds to access complex molecular scaffolds has been a crucial long term goal to execute. In this regard, a series of strategies to achieve Au(I)/Au(III) redox cycles have been reported in the literature. These strategies includes: (a) external oxidant empowered Au(I)/Au(III) catalysis; (b) Au(I)/Au(III) catalysis via merged gold/photoredox catalysis and (c) Au(I)/Au(III) catalysis using ethynylbenziodoxolones (EBXs). The above-mentioned strategies suffer from some inherent disadvantages like: a) the requirement of stoichiometric external oxidants, b) harsh reaction conditions, c) poor functional group tolerance, d) requirement of pre-functionalized substrates, e) low atom economy and f) generation of wastes. Taking these limitations into account, a cost-effective and environmentally benign alternative is proposed herein by merging electrochemistry with gold catalysis for the 1,2-difunctionalization of C-C multiple bonds. The proposed concept employs electricity as a green oxidant to facilitate the Au(I)/Au(III) redox cycle under mild reaction conditions. Be noted that there is no report employing electrochemical oxidative gold catalysis for 1,2-difunctionalization of C-C multiple bonds till date. Being entirely different on the mechanistic front, the methodology once established could furnish novel reactivities and selectivities unachieved by the existing strategies involving oxidative gold catalysis. Undoubtedly, the success of this proposal would open up a new horizon in the field of oxidative gold catalysis

Total Budget (INR):

75,17,587

Organizations involved