Organohypervalent heterocycles

Kumar, Ravi; Dohi, Toshifumi; Zhdankin, Viktor V.

doi:10.1039/d2cs01055k

Cited by 6 publications

(2 citation statements)

References 647 publications

(908 reference statements)

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“…In that direction, several transition metal-free synthetic methodologies have already been developed. [3][4][5][6][7][8][9][10] Arylation reaction has vast potential in generating a variety of biologically active scaffolds and materials with diverse applications. A few review articles have been published recently that advocate the importance of transition metal-free arylation.…”

Section: Introductionmentioning

confidence: 99%

Transition‐Metal Free Arylation of Therapeutically Important Heterocycles

Priyadarshan,

Tripathi,

Venneti

et al. 2024

ChemistrySelect

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The transition‐metal‐free synthesis of organic compounds especially heterocycles is in resonance with one of the twelve principles proposed by Prof. Paul Anastas in his renowned work towards the sustainable development of green chemistry. Traditional‐metal‐catalyzed reactions often involve expensive or toxic metal catalysts, and there is a growing interest in developing more sustainable and environmentally friendly methods. The arylation of heterocycles is an important area of research in organic chemistry, particularly in the synthesis of biologically active compounds and pharmaceuticals. Arylation of heterocycles at different positions enhances the potency and stability of biologically and pharmaceutically important scaffolds. In this review, an overview of the synthetic protocols developed for the arylation of a variety of heterocyclic compounds including, pyrroles, pyridines, thiophene, indole, oxindoles, purines, xanthene, etc. has been described.

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Section: Introductionmentioning

confidence: 99%

Transition‐Metal Free Arylation of Therapeutically Important Heterocycles

Priyadarshan,

Tripathi,

Venneti

et al. 2024

ChemistrySelect

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“…Owing to the large atomic size and wide coordination space, heavy atoms are capable of forming more highly-coordinated states than four-coordinated states, and the structural properties of the resulting compounds have attracted much attention. 1–3 Their coordination flexibility allows the coordination-number shift caused by environmental changes and therefore has been applied as a key component for developing chemical reactions 4–7 and stimuli-responsive systems. 8,9 In the main group elements, the highly-coordinated states can be classified as hypervalent states beyond the octet rule, where hypervalent compounds are characterized by the formation of relatively polarized three-center four-electron (3c–4e) bonds without d orbitals.…”

Section: Introductionmentioning

confidence: 99%

Preparation of seven-coordinated hypervalent tin(iv)-fused azobenzene and applications for stimuli-responsive π-conjugated polymer films

Gon,

Morisaki,

Tanimura

et al. 2024

Dalton Trans.

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Stimuli‐Responsive Optical Materials Based on Hypervalent Antimony‐Containing Conjugated Molecules

Tanimura,

Gon,

Tanaka

et al. 2024

Adv Funct Materials

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Stimuli‐responsive materials have been applied for sensor devices because they can transform and amplify various target stimuli into observable signals. Much effort has been devoted to exploring effective molecular designs for obtaining stimuli‐responsive behaviors by taking advantage of the unique optoelectronic properties of π‐conjugated molecules involving various elements. This study focuses on the modulation of the electronic state of the π‐conjugated scaffolds by the oxidation number change of the hypervalent antimony. This study demonstrate that the strength of the intramolecular interaction between hypervalent antimony and the π‐conjugated framework can be tuned with ligand structure, substituent effect, and oxidation number shifts of hypervalent antimony. In particular, the color changes represented by hypsochromic and bathochromic wavelength shifts of optical bands are achieved by the oxidative reaction of hypervalent antimony in the solid state. Significantly, the direction of the color changes can be confidently predicted by quantum chemical calculations. The findings, based on the electronic interaction between π‐conjugated scaffolds and hypervalent main‐group elements, provide logical design strategies for advanced stimuli‐responsive materials.

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Organohypervalent heterocycles

Abstract: This review summarizes structural and synthetic aspects of heterocyclic molecules incorporating an atom of a hypervalent main-group element. The higher thermal stability of hypervalent heterocycles, as compared to their acyclic analogs, adds special feature to their chemistry.

Cited by 6 publications

References 647 publications

Transition‐Metal Free Arylation of Therapeutically Important Heterocycles

Transition‐Metal Free Arylation of Therapeutically Important Heterocycles

Preparation of seven-coordinated hypervalent tin(iv)-fused azobenzene and applications for stimuli-responsive π-conjugated polymer films

Stimuli‐Responsive Optical Materials Based on Hypervalent Antimony‐Containing Conjugated Molecules

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