Oxidative phenol-arene and phenol-phenol cross-coupling using periodic acid

Peng Cheng Gao; Huan Chen; Vladimir Grigoryants; Qiang Zhang

doi:10.1016/j.tet.2019.02.021

Oxidative phenol-arene and phenol-phenol cross-coupling using periodic acid

Peng Cheng Gao
, Huan Chen
, Vladimir Grigoryants
, Qiang Zhang

Chemistry

University at Albany

SUNY Albany

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

6 Scopus citations

Abstract

A simple, metal-free protocol for unsymmetrical biaryl coupling using H ₅ IO ₆ is reported. H ₅ IO ₆ was evaluated for a novel application in the oxidative cross-coupling of phenol-arene, phenol-phenol, and phenol-naphthol compounds. In this work, most of the couplings were completed within 30 min at ambient temperature. 30 coupling products were conveniently obtained using only 0.5 equivalent of H ₅ IO ₆ in HFIP. A mechanism by which the transformation occurs is proposed.

Original language	English
Pages (from-to)	2004-2011
Number of pages	8
Journal	Tetrahedron
Volume	75
Issue number	13
DOIs	https://doi.org/10.1016/j.tet.2019.02.021
State	Published - Mar 29 2019

Keywords

Metal-free
Oxidative cross-coupling
Periodic acid

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10.1016/j.tet.2019.02.021

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title = "Oxidative phenol-arene and phenol-phenol cross-coupling using periodic acid",

abstract = " A simple, metal-free protocol for unsymmetrical biaryl coupling using H 5 IO 6 is reported. H 5 IO 6 was evaluated for a novel application in the oxidative cross-coupling of phenol-arene, phenol-phenol, and phenol-naphthol compounds. In this work, most of the couplings were completed within 30 min at ambient temperature. 30 coupling products were conveniently obtained using only 0.5 equivalent of H 5 IO 6 in HFIP. A mechanism by which the transformation occurs is proposed.",

keywords = "Metal-free, Oxidative cross-coupling, Periodic acid",

author = "Gao, \{Peng Cheng\} and Huan Chen and Vladimir Grigoryants and Qiang Zhang",

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doi = "10.1016/j.tet.2019.02.021",

language = "English",

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T1 - Oxidative phenol-arene and phenol-phenol cross-coupling using periodic acid

AU - Gao, Peng Cheng

AU - Chen, Huan

AU - Grigoryants, Vladimir

AU - Zhang, Qiang

PY - 2019/3/29

Y1 - 2019/3/29

N2 - A simple, metal-free protocol for unsymmetrical biaryl coupling using H 5 IO 6 is reported. H 5 IO 6 was evaluated for a novel application in the oxidative cross-coupling of phenol-arene, phenol-phenol, and phenol-naphthol compounds. In this work, most of the couplings were completed within 30 min at ambient temperature. 30 coupling products were conveniently obtained using only 0.5 equivalent of H 5 IO 6 in HFIP. A mechanism by which the transformation occurs is proposed.

AB - A simple, metal-free protocol for unsymmetrical biaryl coupling using H 5 IO 6 is reported. H 5 IO 6 was evaluated for a novel application in the oxidative cross-coupling of phenol-arene, phenol-phenol, and phenol-naphthol compounds. In this work, most of the couplings were completed within 30 min at ambient temperature. 30 coupling products were conveniently obtained using only 0.5 equivalent of H 5 IO 6 in HFIP. A mechanism by which the transformation occurs is proposed.

KW - Metal-free

KW - Oxidative cross-coupling

KW - Periodic acid

UR - https://www.scopus.com/pages/publications/85061834628

U2 - 10.1016/j.tet.2019.02.021

DO - 10.1016/j.tet.2019.02.021

M3 - Article

SN - 0040-4020

VL - 75

SP - 2004

EP - 2011

JO - Tetrahedron

JF - Tetrahedron

IS - 13

ER -

Oxidative phenol-arene and phenol-phenol cross-coupling using periodic acid

Abstract

Keywords

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