An expeditious aqueous Suzuki-Miyaura method for the arylation of bromophenols

Joel S. Freundlich; Howard E. Landis

doi:10.1016/j.tetlet.2006.04.027

An expeditious aqueous Suzuki-Miyaura method for the arylation of bromophenols

Joel S. Freundlich, Howard E. Landis

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

38 Scopus citations

Abstract

The development of a novel Suzuki-Miyaura method has been achieved to allow the efficient arylation of bromophenols. A range of functionality is tolerated with regard to the boronic acid coupling partner and the reaction exhibits complete chemoselectivity for the C_aryl-Br bond versus the C_aryl-Cl bond in the aryl halide input. The experimental protocol features a short reaction time of 15 min, utilizes inexpensive Pd/C as a catalyst, and is conducted with water as the solvent.

Original language	English (US)
Pages (from-to)	4275-4279
Number of pages	5
Journal	Tetrahedron Letters
Volume	47
Issue number	25
DOIs	https://doi.org/10.1016/j.tetlet.2006.04.027
State	Published - Jun 19 2006
Externally published	Yes

All Science Journal Classification (ASJC) codes

Biochemistry
Drug Discovery
Organic Chemistry

Keywords

Green chemistry
Microwave chemistry
Phenols
Suzuki-Miyaura coupling

Access to Document

10.1016/j.tetlet.2006.04.027

Cite this

@article{c0e543ef72154dbdb0f7000df381ccec,

title = "An expeditious aqueous Suzuki-Miyaura method for the arylation of bromophenols",

abstract = "The development of a novel Suzuki-Miyaura method has been achieved to allow the efficient arylation of bromophenols. A range of functionality is tolerated with regard to the boronic acid coupling partner and the reaction exhibits complete chemoselectivity for the Caryl-Br bond versus the Caryl-Cl bond in the aryl halide input. The experimental protocol features a short reaction time of 15 min, utilizes inexpensive Pd/C as a catalyst, and is conducted with water as the solvent.",

keywords = "Green chemistry, Microwave chemistry, Phenols, Suzuki-Miyaura coupling",

author = "Freundlich, {Joel S.} and Landis, {Howard E.}",

note = "Funding Information: We would like to thank the Medicines for Malaria Venture for financial support and Dr. Istv{\'a}n Pelczer at the Princeton University NMR facility for aid with NMR experiments. ",

year = "2006",

month = jun,

day = "19",

doi = "10.1016/j.tetlet.2006.04.027",

language = "English (US)",

volume = "47",

pages = "4275--4279",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Limited",

number = "25",

}

TY - JOUR

T1 - An expeditious aqueous Suzuki-Miyaura method for the arylation of bromophenols

AU - Freundlich, Joel S.

AU - Landis, Howard E.

N1 - Funding Information: We would like to thank the Medicines for Malaria Venture for financial support and Dr. István Pelczer at the Princeton University NMR facility for aid with NMR experiments.

PY - 2006/6/19

Y1 - 2006/6/19

N2 - The development of a novel Suzuki-Miyaura method has been achieved to allow the efficient arylation of bromophenols. A range of functionality is tolerated with regard to the boronic acid coupling partner and the reaction exhibits complete chemoselectivity for the Caryl-Br bond versus the Caryl-Cl bond in the aryl halide input. The experimental protocol features a short reaction time of 15 min, utilizes inexpensive Pd/C as a catalyst, and is conducted with water as the solvent.

AB - The development of a novel Suzuki-Miyaura method has been achieved to allow the efficient arylation of bromophenols. A range of functionality is tolerated with regard to the boronic acid coupling partner and the reaction exhibits complete chemoselectivity for the Caryl-Br bond versus the Caryl-Cl bond in the aryl halide input. The experimental protocol features a short reaction time of 15 min, utilizes inexpensive Pd/C as a catalyst, and is conducted with water as the solvent.

KW - Green chemistry

KW - Microwave chemistry

KW - Phenols

KW - Suzuki-Miyaura coupling

UR - http://www.scopus.com/inward/record.url?scp=33646496144&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=33646496144&partnerID=8YFLogxK

U2 - 10.1016/j.tetlet.2006.04.027

DO - 10.1016/j.tetlet.2006.04.027

M3 - Article

AN - SCOPUS:33646496144

SN - 0040-4039

VL - 47

SP - 4275

EP - 4279

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 25

ER -

An expeditious aqueous Suzuki-Miyaura method for the arylation of bromophenols

Abstract

All Science Journal Classification (ASJC) codes

Keywords

Access to Document

Other files and links

Fingerprint

Cite this