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A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones

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Gold-Catalyzed Complementary Nitroalkyne Internal Redox Process: A DFT Study.

K Vipin Raj^1,2, Pawan S Dhote^2,3, Kumar Vanka^1,2

¹Physical and Materials Chemistry Division, CSIR-National Chemical Laboratory, Pune, India.

Frontiers in Chemistry

|July 26, 2021

Summary

This summary is machine-generated.

This study explores gold-catalyzed reactions, focusing on the cycloisomerization of o-nitroarylalkyne derivatives. Theoretical investigations reveal insights into regio-selectivity and the stability of key gold carbene intermediates.

Keywords:

DFT calculation cycloisomerization gold-catalysis internal redox α-oxo gold carbene

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Area of Science:

Organic Synthesis
Organometallic Chemistry
Computational Chemistry

Background:

Gold catalysis has emerged as a powerful tool in modern organic synthesis.
Significant advancements in synthetic methodologies utilizing homogeneous gold catalysis have been achieved over the past two decades.
Reactions involving alpha-oxo gold carbene and alpha-imino gold carbene intermediates are of particular interest due to their synthetic utility and the fundamental questions surrounding their bonding.

Purpose of the Study:

To investigate the theoretical aspects of gold-catalyzed cycloisomerization reactions.
To understand the influence of substitution on the regio-selectivity of these reactions.
To determine the relative stabilities of crucial alpha-oxo gold carbene intermediates.

Main Methods:

Theoretical investigations were employed to study the reaction mechanisms.
Density Functional Theory (DFT) calculations were likely utilized to analyze electronic structures and energy profiles.
Analysis of regio-selectivity based on substituent effects was performed.

Main Results:

The study documents theoretical investigations into the regio-selectivity of gold-catalyzed cycloisomerization of o-nitroarylalkyne derivatives.
The dependence of regio-selectivity on substitution patterns was elucidated.
Relative stabilities of the alpha-oxo gold carbene intermediates were comparatively studied.

Conclusions:

Theoretical insights into the regio-selectivity of gold-catalyzed cycloisomerization reactions were provided.
The findings contribute to a deeper understanding of the factors governing these important synthetic transformations.
This work aids in the rational design of new gold-catalyzed reactions and the synthesis of complex molecules.