Oxidative Cross-Coupling of Two Different Phenols: An Efficient Route to Unsymmetrical Biphenols

Nagnath Yadav More; Masilamani Jeganmohan

doi:10.1021/acs.orglett.5b01324

Oxidative Cross-Coupling of Two Different Phenols: An Efficient Route to Unsymmetrical Biphenols

Nagnath Yadav More
, Masilamani Jeganmohan

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

81 Scopus citations

Abstract

An efficient synthesis of unsymmetrical biphenols via the oxidative cross-coupling of two different phenols in the presence of K₂S₂O₈ and Bu₄N⁺·HSO₃^- (10 mol %) in CF₃COOH at ambient conditions is described. 1:1 Cross-coupling of substituted phenols with naphthols and 1:2 cross-coupling of naphthols with phenol are also disclosed. By using Bu₄N⁺·HSO₃^-, the homocoupling of phenols or naphthols was controlled. In these reactions, the ortho C-H bond of two different phenols and the ortho and para C-H bond of phenols were coupled together.

Original language	English
Pages (from-to)	3042-3045
Number of pages	4
Journal	Organic Letters
Volume	17
Issue number	12
DOIs	https://doi.org/10.1021/acs.orglett.5b01324
State	Published - 19 Jun 2015
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

Access to Document

10.1021/acs.orglett.5b01324

Cite this

@article{60d6025f94734fb48bee1b02238531aa,

title = "Oxidative Cross-Coupling of Two Different Phenols: An Efficient Route to Unsymmetrical Biphenols",

abstract = "An efficient synthesis of unsymmetrical biphenols via the oxidative cross-coupling of two different phenols in the presence of K2S2O8 and Bu4N+·HSO3- (10 mol \%) in CF3COOH at ambient conditions is described. 1:1 Cross-coupling of substituted phenols with naphthols and 1:2 cross-coupling of naphthols with phenol are also disclosed. By using Bu4N+·HSO3-, the homocoupling of phenols or naphthols was controlled. In these reactions, the ortho C-H bond of two different phenols and the ortho and para C-H bond of phenols were coupled together.",

author = "More, \{Nagnath Yadav\} and Masilamani Jeganmohan",

note = "Publisher Copyright: {\textcopyright} 2015 American Chemical Society.",

year = "2015",

month = jun,

day = "19",

doi = "10.1021/acs.orglett.5b01324",

language = "English",

volume = "17",

pages = "3042--3045",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "12",

}

TY - JOUR

T1 - Oxidative Cross-Coupling of Two Different Phenols

T2 - An Efficient Route to Unsymmetrical Biphenols

AU - More, Nagnath Yadav

AU - Jeganmohan, Masilamani

PY - 2015/6/19

Y1 - 2015/6/19

N2 - An efficient synthesis of unsymmetrical biphenols via the oxidative cross-coupling of two different phenols in the presence of K2S2O8 and Bu4N+·HSO3- (10 mol %) in CF3COOH at ambient conditions is described. 1:1 Cross-coupling of substituted phenols with naphthols and 1:2 cross-coupling of naphthols with phenol are also disclosed. By using Bu4N+·HSO3-, the homocoupling of phenols or naphthols was controlled. In these reactions, the ortho C-H bond of two different phenols and the ortho and para C-H bond of phenols were coupled together.

AB - An efficient synthesis of unsymmetrical biphenols via the oxidative cross-coupling of two different phenols in the presence of K2S2O8 and Bu4N+·HSO3- (10 mol %) in CF3COOH at ambient conditions is described. 1:1 Cross-coupling of substituted phenols with naphthols and 1:2 cross-coupling of naphthols with phenol are also disclosed. By using Bu4N+·HSO3-, the homocoupling of phenols or naphthols was controlled. In these reactions, the ortho C-H bond of two different phenols and the ortho and para C-H bond of phenols were coupled together.

UR - https://www.scopus.com/pages/publications/84935009419

U2 - 10.1021/acs.orglett.5b01324

DO - 10.1021/acs.orglett.5b01324

M3 - Article

AN - SCOPUS:84935009419

SN - 1523-7060

VL - 17

SP - 3042

EP - 3045

JO - Organic Letters

JF - Organic Letters

IS - 12

ER -

Oxidative Cross-Coupling of Two Different Phenols: An Efficient Route to Unsymmetrical Biphenols

Abstract

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this