C-CN bond formation: an overview of diverse strategies

Nitrile or cyano compounds are an important part of structural motifs in dyes, agrochemicals, medicinal compounds, and electronic materials. Also, aryl nitrile is an important intermediate in the preparation of numerous compounds via transformations such as hydrolysis, hydration, reduction, cycloadd...

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Published inChemical communications (Cambridge, England) Vol. 57; no. 18; pp. 221 - 2232
Main Authors Pimparkar, Sandeep, Koodan, Adithyaraj, Maiti, Siddhartha, Ahmed, Nesreen S, Mostafa, Mohamed Mokhtar M, Maiti, Debabrata
Format Journal Article
LanguageEnglish
Published England Royal Society of Chemistry 04.03.2021
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Summary:Nitrile or cyano compounds are an important part of structural motifs in dyes, agrochemicals, medicinal compounds, and electronic materials. Also, aryl nitrile is an important intermediate in the preparation of numerous compounds via transformations such as hydrolysis, hydration, reduction, cycloadditions, and nucleophilic additions. Such methods are beneficial for introducing sensitive functional groups in various positions in the multi-step synthesis of natural products and medicinal compounds. In the past decades, various cyanation methods have been reported in the vast arena of chemistry, which have made several building blocks accessible. Previously reported cyanation reviews, letters, and perspectives are written in parts. Thus, today a comprehensive review that will be able to guide readers through the vast pool of C-CN bond forming reactions via different approaches is obligatory. The present feature article depicts the various areas of cyanation methodologies that are based on the metal catalyst used, directed, non-directed, electrochemical, photochemical, asymmetric, and radical based approaches. This feature article will serve as a comprehensive tool to navigate the C-CN (cyanation) reactions across the vast area in synthetic chemistry. Aim for cyanation : a comprehensive overview on various approaches on C-CN bond formation in arenes/heteroarenes by activated halides/pseudohalide, directed, non-directed, electro-catalyzed, photoredox-catalyzed, and radical approaches.
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Prof. Dr Debabrata Maiti received his PhD from John Hopkins University (USA) in 2008 under the supervision of Prof. Kenneth D. Karlin. After postdoctoral studies at the Massachusetts Institute of Technology (MIT) with Prof. Stephen L. Buchwald (2008-2010), he joined the Department of Chemistry at IIT Bombay in 2011. His research interests are focused on the development of new and sustainable synthetic and catalytic methods, aliphatic & aromatic distal C-H activation, photocatalysis, electrocatalysis, heterocycle synthesis, and lignin valorisation.
Dr. Sandeep Pimparkar was born and brought up in Nasik (Maharashtra) India. After his MSc in organic chemistry, he joined as a junior research fellow at IISER Pune, India with Dr. M. Jeganmohan. Later, in 2015, he joined Prof. Debabrata Maiti's research group for PhD at IIT Bombay (IITB-Monash Research Academy). During his PhD, he mainly studied the design & discovery of templates for distal C-H activation of aliphatic and aromatics by using transition metal catalysis.
Prof. Dr Nesreen S. Ahmed completed her Master of Science in 1996 from Ain Shams University, Cairo, Egypt and a PhD in 2000 from the same University. She was an assistant Professor of Organic Chemistry at the Department of Therapeutic Chemistry, Pharmaceutical, and Drug Industries Research Division, National Research Center (NRC), Dokki, Cairo, Egypt. She was delegated as Associate Professor (2006-2018) in the Department of Chemistry at the King Abdulaziz University (KAU), Jeddah, Saudi Arabia. Her scientific interest is in medicinal chemistry, heterocyclic compounds, and green chemistry. She is experienced in the preparation, elucidation, and biological tests of new organic compounds.
Mr. Adithyaraj Koodan was born and brought up in Kerala, India. He obtained his Integrated MSc in chemistry from Integrated Science Education and Research Centre, Visva-Bharati, India. He did his final year MSc dissertation project under Prof. Debabarata Maiti from Indian Institute of Technology Bombay, India on transition metal catalyzed remote C-H functionalization reactions.
Prof. Dr Mohamed Mokhtar got his Master's degree in 1993 from Zagazig University and PhD in 1997 from Cairo University, Cairo, Egypt. He was a researcher from DAAD, in Karlsruhe, Germany in 1998-1999. He was invited as a research fellow to the Surface Chemistry and Catalysis Department, Ulm University, Ulm, Germany in 2003 and at Erlangen-Nuremberg University (FAU), Germany in 2007. His dual roles at the NRC and the KAU are just the latest in a string of leadership roles he has held in the scientific research field for almost 30 years. His focus is in advanced materials and heterogeneous catalysis.
ions under the supervision of Prof. Maolin Guo. He then studied the amidosulfates-mediated peptide formation under potential early-earth conditions at the Indian Institute of Technology, Bombay with Prof. Samir Maji, and Prof. Debabrata Maiti. He is now appointed as Assistant Professor at Vellore Institute of Technology, Bhopal, India in the Bioengineering department.
Prof. Dr Siddhartha Maiti was born in India. In 2016 for his PhD at the University of Massachusetts Dartmouth (USA), he studied the development of fluorescent sensor for the bioimaging of iron
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ISSN:1359-7345
1364-548X
DOI:10.1039/d0cc07783f