Single and double Suzuki-Miyaura couplings with symmetric dihalobenzenes

David J. Sinclair; Michael S. Sherburn

doi:10.1021/jo050105q

Single and double Suzuki-Miyaura couplings with symmetric dihalobenzenes

David J. Sinclair, Michael S. Sherburn^*

^*Corresponding author for this work

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

106 Citations (Scopus)

Abstract

(Chemical Equation Presented) m- or p-diiodobenzene undergoes selective double coupling reactions with arylboronic acids and esters. Selectivity for double coupling over single coupling is remarkably strong: even with a diiodobenzene:monoboronic acid ratio of 10:1, the products of double coupling are formed in good yields. Steric hindrance and electronic influences of the boronic acid or ester, and reaction conditions do not appear to impact significantly upon the outcome of the reaction. In contrast, m- and p-dibromobenzenes undergo single couplings with aryl boronic acids with high selectivity.

Original language	English
Pages (from-to)	3730-3733
Number of pages	4
Journal	Journal of Organic Chemistry
Volume	70
Issue number	9
DOIs	https://doi.org/10.1021/jo050105q
Publication status	Published - 29 Apr 2005

Access to Document

10.1021/jo050105q

Cite this

@article{0498ad1b6aa7425c8c4711b48a43ef7c,

title = "Single and double Suzuki-Miyaura couplings with symmetric dihalobenzenes",

abstract = "(Chemical Equation Presented) m- or p-diiodobenzene undergoes selective double coupling reactions with arylboronic acids and esters. Selectivity for double coupling over single coupling is remarkably strong: even with a diiodobenzene:monoboronic acid ratio of 10:1, the products of double coupling are formed in good yields. Steric hindrance and electronic influences of the boronic acid or ester, and reaction conditions do not appear to impact significantly upon the outcome of the reaction. In contrast, m- and p-dibromobenzenes undergo single couplings with aryl boronic acids with high selectivity.",

author = "Sinclair, {David J.} and Sherburn, {Michael S.}",

year = "2005",

month = apr,

day = "29",

doi = "10.1021/jo050105q",

language = "English",

volume = "70",

pages = "3730--3733",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

number = "9",

}

TY - JOUR

T1 - Single and double Suzuki-Miyaura couplings with symmetric dihalobenzenes

AU - Sinclair, David J.

AU - Sherburn, Michael S.

PY - 2005/4/29

Y1 - 2005/4/29

N2 - (Chemical Equation Presented) m- or p-diiodobenzene undergoes selective double coupling reactions with arylboronic acids and esters. Selectivity for double coupling over single coupling is remarkably strong: even with a diiodobenzene:monoboronic acid ratio of 10:1, the products of double coupling are formed in good yields. Steric hindrance and electronic influences of the boronic acid or ester, and reaction conditions do not appear to impact significantly upon the outcome of the reaction. In contrast, m- and p-dibromobenzenes undergo single couplings with aryl boronic acids with high selectivity.

AB - (Chemical Equation Presented) m- or p-diiodobenzene undergoes selective double coupling reactions with arylboronic acids and esters. Selectivity for double coupling over single coupling is remarkably strong: even with a diiodobenzene:monoboronic acid ratio of 10:1, the products of double coupling are formed in good yields. Steric hindrance and electronic influences of the boronic acid or ester, and reaction conditions do not appear to impact significantly upon the outcome of the reaction. In contrast, m- and p-dibromobenzenes undergo single couplings with aryl boronic acids with high selectivity.

UR - http://www.scopus.com/inward/record.url?scp=17744384723&partnerID=8YFLogxK

U2 - 10.1021/jo050105q

DO - 10.1021/jo050105q

M3 - Article

SN - 0022-3263

VL - 70

SP - 3730

EP - 3733

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 9

ER -

Single and double Suzuki-Miyaura couplings with symmetric dihalobenzenes

Abstract

Access to Document

Other files and links

Fingerprint

Cite this