Iodine(III)-Catalyzed Formal [2 + 2 + 1] Cycloaddition Reaction for Metal-Free Construction of Oxazoles

Takuma Yagyu, Yusuke Takemoto, Akira Yoshimura, Viktor V. Zhdankin, Akio Saito

Research output: Contribution to journalArticle

31 Citations (Scopus)

Abstract

The iodine(III) catalyst, in situ generated from iodoarene as a precatalyst with m-CPBA and Tf2NH, promoted the metal-free [2 + 2 + 1] cycloaddition-type reactions of alkynes, nitriles, and oxygen atoms for the regioselective formations of 2,4-disubstituted and 2,4,5-trisubstituted oxazole. A first example of iodine catalysis for multicomponent reactions is represented.

Original languageEnglish
Pages (from-to)2506-2509
Number of pages4
JournalOrganic Letters
Volume19
Issue number10
DOIs
Publication statusPublished - 19 May 2017
Externally publishedYes

Fingerprint

Oxazoles
oxazole
Cycloaddition
Cycloaddition Reaction
cycloaddition
Iodine
iodine
Metals
Nitriles
Alkynes
nitriles
alkynes
Catalysis
metals
catalysis
atoms
oxygen atoms
Oxygen
catalysts
Atoms

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

Iodine(III)-Catalyzed Formal [2 + 2 + 1] Cycloaddition Reaction for Metal-Free Construction of Oxazoles. / Yagyu, Takuma; Takemoto, Yusuke; Yoshimura, Akira; Zhdankin, Viktor V.; Saito, Akio.

In: Organic Letters, Vol. 19, No. 10, 19.05.2017, p. 2506-2509.

Research output: Contribution to journalArticle

@article{608606356d5f48bfab285b96f8351a44,
title = "Iodine(III)-Catalyzed Formal [2 + 2 + 1] Cycloaddition Reaction for Metal-Free Construction of Oxazoles",
abstract = "The iodine(III) catalyst, in situ generated from iodoarene as a precatalyst with m-CPBA and Tf2NH, promoted the metal-free [2 + 2 + 1] cycloaddition-type reactions of alkynes, nitriles, and oxygen atoms for the regioselective formations of 2,4-disubstituted and 2,4,5-trisubstituted oxazole. A first example of iodine catalysis for multicomponent reactions is represented.",
author = "Takuma Yagyu and Yusuke Takemoto and Akira Yoshimura and Zhdankin, {Viktor V.} and Akio Saito",
year = "2017",
month = "5",
day = "19",
doi = "10.1021/acs.orglett.7b00742",
language = "English",
volume = "19",
pages = "2506--2509",
journal = "Organic Letters",
issn = "1523-7060",
publisher = "American Chemical Society",
number = "10",

}

TY - JOUR

T1 - Iodine(III)-Catalyzed Formal [2 + 2 + 1] Cycloaddition Reaction for Metal-Free Construction of Oxazoles

AU - Yagyu, Takuma

AU - Takemoto, Yusuke

AU - Yoshimura, Akira

AU - Zhdankin, Viktor V.

AU - Saito, Akio

PY - 2017/5/19

Y1 - 2017/5/19

N2 - The iodine(III) catalyst, in situ generated from iodoarene as a precatalyst with m-CPBA and Tf2NH, promoted the metal-free [2 + 2 + 1] cycloaddition-type reactions of alkynes, nitriles, and oxygen atoms for the regioselective formations of 2,4-disubstituted and 2,4,5-trisubstituted oxazole. A first example of iodine catalysis for multicomponent reactions is represented.

AB - The iodine(III) catalyst, in situ generated from iodoarene as a precatalyst with m-CPBA and Tf2NH, promoted the metal-free [2 + 2 + 1] cycloaddition-type reactions of alkynes, nitriles, and oxygen atoms for the regioselective formations of 2,4-disubstituted and 2,4,5-trisubstituted oxazole. A first example of iodine catalysis for multicomponent reactions is represented.

UR - http://www.scopus.com/inward/record.url?scp=85019350529&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85019350529&partnerID=8YFLogxK

U2 - 10.1021/acs.orglett.7b00742

DO - 10.1021/acs.orglett.7b00742

M3 - Article

VL - 19

SP - 2506

EP - 2509

JO - Organic Letters

JF - Organic Letters

SN - 1523-7060

IS - 10

ER -