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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Veröffentlicht in:Organic & biomolecular chemistry 2024-05, Vol.22 (19), p.3772-3798
Hauptverfasser: Das, Bubul, Dahiya, Anjali, Patel, Bhisma K
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Sprache:eng
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Zusammenfassung: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.
ISSN:1477-0520
1477-0539
DOI:10.1039/d4ob00281d