Iodonium salts as efficient iodine(III)-based noncovalent organocatalysts for Knorr-type reactions

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Iodonium salts as efficient iodine(III)-based noncovalent organocatalysts for Knorr-type reactions. / Yunusova, Sevilya N.; Novikov, Alexander S.; Soldatova, Natalia S.; Vovk, Mikhail A.; Bolotin, Dmitrii S.

In: RSC Advances, Vol. 11, No. 8, 22.01.2021, p. 4574–4583.

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

BibTeX

@article{0c067ee043924bac8b106b5a165b8b79,

title = "Iodonium salts as efficient iodine(III)-based noncovalent organocatalysts for Knorr-type reactions",

abstract = "Hypervalent iodine(iii)-derivatives display higher catalytic activity than other aliphatic and aromatic iodine(i)- or bromine(i)-containing substrates for a Knorr-type reaction of N-acetyl hydrazides with acetyl acetone to give N-acyl pyrazoles. The highest activity was observed for dibenziodolium triflate, for which 10 mol% resulted in the generation of N-acyl pyrazole from acyl hydrazide and acetyl acetone typically at 50 °C for 3.5-6 h with up to 99% isolated yields. 1H NMR titration data and DFT calculations indicate that the catalytic activity of the iodine(iii) is caused by the binding with a ketone. This journal is",

keywords = "Нековалентный катализ, иодониевые соли, механизм реакции, BRONSTED ACID, HALOGEN BONDS, ASYMMETRIC ORGANOCATALYSIS, ORGANIC-SYNTHESIS, CATALYSIS, COMPLEXES, SUBSTITUTION, ACTIVATION, PRODUCTS, ELEMENTS",

author = "Yunusova, {Sevilya N.} and Novikov, {Alexander S.} and Soldatova, {Natalia S.} and Vovk, {Mikhail A.} and Bolotin, {Dmitrii S.}",

note = "Publisher Copyright: {\textcopyright} The Royal Society of Chemistry.",

year = "2021",

month = jan,

day = "22",

doi = "10.1039/D0RA09640G",

language = "English",

volume = "11",

pages = "4574–4583",

journal = "RSC Advances",

issn = "2046-2069",

publisher = "Royal Society of Chemistry",

number = "8",

}

RIS

TY - JOUR

T1 - Iodonium salts as efficient iodine(III)-based noncovalent organocatalysts for Knorr-type reactions

AU - Yunusova, Sevilya N.

AU - Novikov, Alexander S.

AU - Soldatova, Natalia S.

AU - Vovk, Mikhail A.

AU - Bolotin, Dmitrii S.

N1 - Publisher Copyright: © The Royal Society of Chemistry.

PY - 2021/1/22

Y1 - 2021/1/22

N2 - Hypervalent iodine(iii)-derivatives display higher catalytic activity than other aliphatic and aromatic iodine(i)- or bromine(i)-containing substrates for a Knorr-type reaction of N-acetyl hydrazides with acetyl acetone to give N-acyl pyrazoles. The highest activity was observed for dibenziodolium triflate, for which 10 mol% resulted in the generation of N-acyl pyrazole from acyl hydrazide and acetyl acetone typically at 50 °C for 3.5-6 h with up to 99% isolated yields. 1H NMR titration data and DFT calculations indicate that the catalytic activity of the iodine(iii) is caused by the binding with a ketone. This journal is

AB - Hypervalent iodine(iii)-derivatives display higher catalytic activity than other aliphatic and aromatic iodine(i)- or bromine(i)-containing substrates for a Knorr-type reaction of N-acetyl hydrazides with acetyl acetone to give N-acyl pyrazoles. The highest activity was observed for dibenziodolium triflate, for which 10 mol% resulted in the generation of N-acyl pyrazole from acyl hydrazide and acetyl acetone typically at 50 °C for 3.5-6 h with up to 99% isolated yields. 1H NMR titration data and DFT calculations indicate that the catalytic activity of the iodine(iii) is caused by the binding with a ketone. This journal is

KW - Нековалентный катализ

KW - иодониевые соли

KW - механизм реакции

KW - BRONSTED ACID

KW - HALOGEN BONDS

KW - ASYMMETRIC ORGANOCATALYSIS

KW - ORGANIC-SYNTHESIS

KW - CATALYSIS

KW - COMPLEXES

KW - SUBSTITUTION

KW - ACTIVATION

KW - PRODUCTS

KW - ELEMENTS

UR - http://www.scopus.com/inward/record.url?scp=85100015489&partnerID=8YFLogxK

UR - https://www.mendeley.com/catalogue/15333fa7-15d5-3a56-988c-62e2c3b15a99/

U2 - 10.1039/D0RA09640G

DO - 10.1039/D0RA09640G

M3 - Article

AN - SCOPUS:85100015489

VL - 11

SP - 4574

EP - 4583

JO - RSC Advances

JF - RSC Advances

SN - 2046-2069

IS - 8

ER -

ID: 73230395