Comparative Study of the Catalytic Activity of Hypervalent Halogen(III) and Chalcogen(IV) Salts in the Imine–Isocyanide Coupling

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Comparative Study of the Catalytic Activity of Hypervalent Halogen(III) and Chalcogen(IV) Salts in the Imine–Isocyanide Coupling. / Сафинская, Яна Валерьевна ; Ильин, Михаил Вячеславович.

In: Russian Journal of General Chemistry, Vol. 94, No. 10, 19.11.2024, p. 2632–2637.

Research output: Contribution to journal › Article › peer-review

BibTeX

@article{94a3998ffcd14bd4a29c2ec9a496d14c,

title = "Comparative Study of the Catalytic Activity of Hypervalent Halogen(III) and Chalcogen(IV) Salts in the Imine–Isocyanide Coupling",

abstract = "Abstract: In this study, the catalytic activity of halonium and chalconium salts was explored, and special attention was focused on their application as σ-hole donating species in noncovalent organocatalysis. The catalytic performance of a series of halonium (ClIII, BrIII, IIII) and chalconium (SIV, SeIV, TeIV) salts was evaluated in the imine–isocyanide coupling, which is a key method for synthesizing biologically active compounds being one of the steps of Groebke–Blackburn–Bienaym{\'e} reaction. Analysis of the kinetic data obtained via utilization of 1H NMR spectroscopy revealed that the iodine-based salt demonstrated the highest activity among the chosen halogen bond donors, while telluronium salt outperformed their sulfonium and selenonium counterparts in the chalcogen bond donating moiety.",

keywords = "chalcogen bonding, electrophilic activation, halogen bonding, noncovalent organocatalysis, σ-hole interactions",

author = "Сафинская, {Яна Валерьевна} and Ильин, {Михаил Вячеславович}",

year = "2024",

month = nov,

day = "19",

doi = "10.1134/S1070363224100086",

language = "English",

volume = "94",

pages = "2632–2637",

journal = "Russian Journal of General Chemistry",

issn = "1070-3632",

publisher = "МАИК {"}Наука/Интерпериодика{"}",

number = "10",

}

RIS

TY - JOUR

T1 - Comparative Study of the Catalytic Activity of Hypervalent Halogen(III) and Chalcogen(IV) Salts in the Imine–Isocyanide Coupling

AU - Сафинская, Яна Валерьевна

AU - Ильин, Михаил Вячеславович

PY - 2024/11/19

Y1 - 2024/11/19

N2 - Abstract: In this study, the catalytic activity of halonium and chalconium salts was explored, and special attention was focused on their application as σ-hole donating species in noncovalent organocatalysis. The catalytic performance of a series of halonium (ClIII, BrIII, IIII) and chalconium (SIV, SeIV, TeIV) salts was evaluated in the imine–isocyanide coupling, which is a key method for synthesizing biologically active compounds being one of the steps of Groebke–Blackburn–Bienaymé reaction. Analysis of the kinetic data obtained via utilization of 1H NMR spectroscopy revealed that the iodine-based salt demonstrated the highest activity among the chosen halogen bond donors, while telluronium salt outperformed their sulfonium and selenonium counterparts in the chalcogen bond donating moiety.

AB - Abstract: In this study, the catalytic activity of halonium and chalconium salts was explored, and special attention was focused on their application as σ-hole donating species in noncovalent organocatalysis. The catalytic performance of a series of halonium (ClIII, BrIII, IIII) and chalconium (SIV, SeIV, TeIV) salts was evaluated in the imine–isocyanide coupling, which is a key method for synthesizing biologically active compounds being one of the steps of Groebke–Blackburn–Bienaymé reaction. Analysis of the kinetic data obtained via utilization of 1H NMR spectroscopy revealed that the iodine-based salt demonstrated the highest activity among the chosen halogen bond donors, while telluronium salt outperformed their sulfonium and selenonium counterparts in the chalcogen bond donating moiety.

KW - chalcogen bonding

KW - electrophilic activation

KW - halogen bonding

KW - noncovalent organocatalysis

KW - σ-hole interactions

UR - https://www.mendeley.com/catalogue/54da7f85-5257-3dd9-8ab8-d4bd000d4b41/

U2 - 10.1134/S1070363224100086

DO - 10.1134/S1070363224100086

M3 - Article

VL - 94

SP - 2632

EP - 2637

JO - Russian Journal of General Chemistry

JF - Russian Journal of General Chemistry

SN - 1070-3632

IS - 10

ER -

ID: 126788600