Synthetic Utilization of Polynitro Aromatic Compounds. 5. Multi-Centered Reactivity Pattern in Reactions of 4,6-Dinitro-1,2-benzisothiazoles and -isothiazol-3(2H)-ones with C-, N-, O-, S-, and F-Nucleophiles

Gakh, Andrei A.; Zlotin, Sergei G.; Kislitsin, P. G.; Kucherov, Fedor A.; Serebryakov, Evgeny A.; Strelenko, Yury A.

doi:10.3987/com-06-10862

Cited by 6 publications

(1 citation statement)

References 4 publications

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“…In vicarious nucleophilic substitution, the nucleophile carries a leaving group X in the α position, so that HX can be eliminated upon nucleophilic attack to an electron-deficient arene, often an arene with a π-accepting functional group, such as nitro arenes (Scheme ). Elimination initially forms an exocyclic double bond, and subsequent tautomerization restores aromaticity with a formal replacement of the hydride by a nucleophile. The two-electron oxidation equivalent is inherent to the nucleophile–X bond that is no longer present in the product.…”

Section: Nucleophilic Aromatic Substitution (Snar)mentioning

confidence: 99%

A Perspective on Late-Stage Aromatic C–H Bond Functionalization

2022

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Late-stage functionalization of C–H bonds (C–H LSF) can provide a straightforward approach to the efficient synthesis of functionalized complex molecules. However, C–H LSF is challenging because the C–H bond must be functionalized in the presence of various other functional groups. In this Perspective, we evaluate aromatic C–H LSF on the basis of four criteriareactivity, chemoselectivity, site-selectivity, and substrate scopeand provide our own views on current challenges as well as promising strategies and areas of growth going forward.

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Section: Nucleophilic Aromatic Substitution (Snar)mentioning

confidence: 99%