Issue 19, 2024

Isothiocyanates: happy-go-lucky reagents in organic synthesis

Abstract

Owing to their unique structural features, isothiocyanates (ITCs) are a class of highly useful and inimitable reagents as the –N[double bond, length as m-dash]C[double bond, length as m-dash]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[double bond, length as m-dash]C[double bond, length as m-dash]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.

Graphical abstract: Isothiocyanates: happy-go-lucky reagents in organic synthesis

Article information

Article type
Review Article
Submitted
21 Feb 2024
Accepted
18 Apr 2024
First published
19 Apr 2024

Org. Biomol. Chem., 2024,22, 3772-3798

Isothiocyanates: happy-go-lucky reagents in organic synthesis

B. Das, A. Dahiya and B. K. Patel, Org. Biomol. Chem., 2024, 22, 3772 DOI: 10.1039/D4OB00281D

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