Isothiocyanates: happy-go-lucky reagents in organic synthesis
Owing to their unique structural features, isothiocyanates (ITCs) are a class of highly useful and inimitable reagents as the -N&z.dbd;C&z.dbd;S group serves both as electrophile and nucleophile in organic synthesis. ITCs share a rich legacy in organic, medicinal, and combinatorial chemistry...
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| Published in | Organic & biomolecular chemistry Vol. 22; no. 19; pp. 3772 - 3798 |
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| Main Authors | , , |
| Format | Journal Article |
| Language | English |
| Published |
England
Royal Society of Chemistry
15.05.2024
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| Subjects | |
| Online Access | Get full text |
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| Summary: | Owing to their unique structural features, isothiocyanates (ITCs) are a class of highly useful and inimitable reagents as the -N&z.dbd;C&z.dbd;S group serves both as electrophile and nucleophile in organic synthesis. ITCs share a rich legacy in organic, medicinal, and combinatorial chemistry. Compared to their oxygen equivalents, isocyanates, ITCs are easily available, less unpleasant, and somewhat less harmful to work with (mild conditions) which makes them happy-go-lucky reagents. Functionalized ITCs can finely tune the reactivity of the -N&z.dbd;C&z.dbd;S group and thus can be exploited in the late-stage functionalization processes. This review's primary aim is to outline ITC chemistry in the construction and derivatization of heterocycles through the lens of sustainability. For ease and brevity, the sections are divided based on reactive centers present in functionalized ITCs and modes of cyclisation. Scrutinizing their probable unexplored directions for future research studies is also addressed.
This review summarises the reactivity and synthetic procedures of aryl and acyl isothiocyanates, a versatile reagent with multiple reactive centres. |
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| Bibliography: | Bubul Das was born in 1996 in Assam, India. He received his BSc. from Nalbari College, Gauhati University in 2017 and his M.Sc. from Delhi University in 2019. He qualified for the CSIR National Eligibility Test (2018) & GATE (2019) and is currently pursuing his doctoral research under the supervision of Prof. Bhisma K. Patel at the Indian Institute of Technology Guwahati (India) and simultaneously serving as an Assistant Professor at Bagadhar Brahma Kishan College, Jalah, Assam. His research primarily focuses on transition metal-catalyzed C-H bond activation and annulation reaction. Anjali Dahiya was born in 1993 in Haryana, India. She received her BSc (Hons.) and MSc. degrees from Hansraj College, Delhi University in 2013 and 2016 respectively. She qualified for the CSIR National Eligibility Test & GATE in 2016 and did her doctoral research under the supervision of Prof. Bhisma K. Patel at the Indian Institute of Technology in Guwahati (India). Her Ph.D. research was focused on the metal-free cascade reaction of aroyl isothiocyanates and arenediazonium salts. Since 2023, she has been working as a postdoctoral fellow with Prof. Patrick Y. Toullec at the University of Bordeaux. Her current research is to develop novel methodologies involving electrophilic activation of alkynes by chiral Brønsted acids. Bhisma Kumar Patel (born in August 1965) received his B.Sc (Hons) and M.Sc degrees from Sambalpur University, Odisha, India. He was admitted to IIT Kanpur for his PhD in the research group of Prof. S. Ranganathan (FNA) (1988-1994). After three years of post-doctoral tenure with Prof. Dr Fritz Eckstein at the Max Planck Institute for Experimental Medicine (1994-1997), he joined the Department of Chemistry, Indian Institute of Technology Guwahati as an Assistant Professor in April 1997, where he was elevated to the post of Full Professor in August 2005, and HAG Professor in September 2011 and continued as the Head of the Department. His current research interests include Photochemistry, electro chemistry, green chemistry, C-H activation, cross dehydrogenative coupling, metal-catalyzed/metal-free oxidative functionalization, multi-component reactions, and hypervalent iodine-mediated organic transformations. Altogether 30 students have been awarded the PhD degree under his supervision and his research work has resulted in the publication of 198 research papers in journals of international repute and three patents. ObjectType-Article-2 SourceType-Scholarly Journals-1 ObjectType-Feature-3 content type line 23 ObjectType-Review-1 |
| ISSN: | 1477-0520 1477-0539 |
| DOI: | 10.1039/d4ob00281d |