Synthesis of arylbenziodoxoles using pseudocyclic benziodoxole triflate and arenes

Akira Yoshimura; Scott M. Larson; Gunnar B. Frahm; Christopher D. Huss; Gregory T. Rohde; Victor N. Nemykin; Mekhman S. Yusubov; Akio Saito; Viktor V. Zhdankin

doi:10.24820/ARK.5550190.P011.324

Synthesis of arylbenziodoxoles using pseudocyclic benziodoxole triflate and arenes

Akira Yoshimura, Scott M. Larson, Gunnar B. Frahm, Christopher D. Huss, Gregory T. Rohde, Victor N. Nemykin, Mekhman S. Yusubov, Akio Saito, Viktor V. Zhdankin

Chemistry & Biochemistry

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

4 Scopus citations

Abstract

An acid activated pseudocyclic hypervalent iodine reagent, 2-[hydroxy(trifluoromethanesufonyloxy)]-iodobenzoic acid, can easily react with various arenes in the presence of trifluoromethanesulfonic acid to produce pseudocyclic diaryliodonium triflate salts. This synthetic procedure proceeds under mild conditions to afford the respective iodonium salts in moderate to good yields. Several pseudocyclic diaryliodonium triflate salts structures have been confirmed by X-ray crystallography. Obtained products can be easily converted to cyclic hypervalent iodine(III) compounds, arylbenziodoxolones, in moderate to good yields under basic conditions.

Original language	English (US)
Journal	Arkivoc
Volume	2020
Issue number	4
DOIs	https://doi.org/10.24820/ARK.5550190.P011.324
State	Published - Sep 24 2020

Bibliographical note

Funding Information:
This work was supported by a research grant from the Russian Science Foundation (RSF-16-13-10081-P) and National Science Foundation (CHE-1759798). A.S. is thankful to JSPS Fund for the Promotion of Joint International Research (Grant No 16KK0199) and JST CREST (No. JRMJCR19R2).

Publisher Copyright:
© 2020 Arkat. All rights reserved.

Keywords

Arylbenziodoxolones
Benziodoxole
Cyclization
Hypervalent iodine reagent
Pseudocyclic diaryliodonium salts

Access

10.24820/ARK.5550190.P011.324

OpenUrl availability

Full text

Cite this

@article{0676e587607e4768995e0774fe4daf7c,

title = "Synthesis of arylbenziodoxoles using pseudocyclic benziodoxole triflate and arenes",

abstract = "An acid activated pseudocyclic hypervalent iodine reagent, 2-[hydroxy(trifluoromethanesufonyloxy)]-iodobenzoic acid, can easily react with various arenes in the presence of trifluoromethanesulfonic acid to produce pseudocyclic diaryliodonium triflate salts. This synthetic procedure proceeds under mild conditions to afford the respective iodonium salts in moderate to good yields. Several pseudocyclic diaryliodonium triflate salts structures have been confirmed by X-ray crystallography. Obtained products can be easily converted to cyclic hypervalent iodine(III) compounds, arylbenziodoxolones, in moderate to good yields under basic conditions.",

keywords = "Arylbenziodoxolones, Benziodoxole, Cyclization, Hypervalent iodine reagent, Pseudocyclic diaryliodonium salts",

author = "Akira Yoshimura and Larson, {Scott M.} and Frahm, {Gunnar B.} and Huss, {Christopher D.} and Rohde, {Gregory T.} and Nemykin, {Victor N.} and Yusubov, {Mekhman S.} and Akio Saito and Zhdankin, {Viktor V.}",

note = "Funding Information: This work was supported by a research grant from the Russian Science Foundation (RSF-16-13-10081-P) and National Science Foundation (CHE-1759798). A.S. is thankful to JSPS Fund for the Promotion of Joint International Research (Grant No 16KK0199) and JST CREST (No. JRMJCR19R2). Publisher Copyright: {\textcopyright} 2020 Arkat. All rights reserved.",

year = "2020",

month = sep,

day = "24",

doi = "10.24820/ARK.5550190.P011.324",

language = "English (US)",

volume = "2020",

journal = "Arkivoc",

issn = "1551-7004",

publisher = "Arkat USA",

number = "4",

}

TY - JOUR

T1 - Synthesis of arylbenziodoxoles using pseudocyclic benziodoxole triflate and arenes

AU - Yoshimura, Akira

AU - Larson, Scott M.

AU - Frahm, Gunnar B.

AU - Huss, Christopher D.

AU - Rohde, Gregory T.

AU - Nemykin, Victor N.

AU - Yusubov, Mekhman S.

AU - Saito, Akio

AU - Zhdankin, Viktor V.

N1 - Funding Information: This work was supported by a research grant from the Russian Science Foundation (RSF-16-13-10081-P) and National Science Foundation (CHE-1759798). A.S. is thankful to JSPS Fund for the Promotion of Joint International Research (Grant No 16KK0199) and JST CREST (No. JRMJCR19R2). Publisher Copyright: © 2020 Arkat. All rights reserved.

PY - 2020/9/24

Y1 - 2020/9/24

N2 - An acid activated pseudocyclic hypervalent iodine reagent, 2-[hydroxy(trifluoromethanesufonyloxy)]-iodobenzoic acid, can easily react with various arenes in the presence of trifluoromethanesulfonic acid to produce pseudocyclic diaryliodonium triflate salts. This synthetic procedure proceeds under mild conditions to afford the respective iodonium salts in moderate to good yields. Several pseudocyclic diaryliodonium triflate salts structures have been confirmed by X-ray crystallography. Obtained products can be easily converted to cyclic hypervalent iodine(III) compounds, arylbenziodoxolones, in moderate to good yields under basic conditions.

AB - An acid activated pseudocyclic hypervalent iodine reagent, 2-[hydroxy(trifluoromethanesufonyloxy)]-iodobenzoic acid, can easily react with various arenes in the presence of trifluoromethanesulfonic acid to produce pseudocyclic diaryliodonium triflate salts. This synthetic procedure proceeds under mild conditions to afford the respective iodonium salts in moderate to good yields. Several pseudocyclic diaryliodonium triflate salts structures have been confirmed by X-ray crystallography. Obtained products can be easily converted to cyclic hypervalent iodine(III) compounds, arylbenziodoxolones, in moderate to good yields under basic conditions.

KW - Arylbenziodoxolones

KW - Benziodoxole

KW - Cyclization

KW - Hypervalent iodine reagent

KW - Pseudocyclic diaryliodonium salts

UR - http://www.scopus.com/inward/record.url?scp=85094161226&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85094161226&partnerID=8YFLogxK

U2 - 10.24820/ARK.5550190.P011.324

DO - 10.24820/ARK.5550190.P011.324

M3 - Article

AN - SCOPUS:85094161226

SN - 1551-7004

VL - 2020

JO - Arkivoc

JF - Arkivoc

IS - 4

ER -

Synthesis of arylbenziodoxoles using pseudocyclic benziodoxole triflate and arenes

Abstract

Bibliographical note

Keywords

Access

OpenUrl availability

Other files and links

Fingerprint

Cite this