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Double Suzuki cross‐coupling reaction of pyrimidine boronic acid: synthesis of new versatile dielectrophile
Author(s) -
Naseer Muhammad Moazzam,
Hameed Shahid
Publication year - 2012
Publication title -
applied organometallic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.53
H-Index - 71
eISSN - 1099-0739
pISSN - 0268-2605
DOI - 10.1002/aoc.2865
Subject(s) - chemistry , suzuki reaction , aniline , boronic acid , supramolecular chemistry , reactivity (psychology) , coupling reaction , nucleophile , combinatorial chemistry , pyrimidine , reactive intermediate , polymer chemistry , organic chemistry , aryl , stereochemistry , molecule , catalysis , medicine , alkyl , alternative medicine , pathology
The double Suzuki cross‐coupling reaction has successfully been applied for the synthesis of 5,5′‐(5‐butoxy‐1,3‐phenylene)bis(2‐chloropyrimidine) with two reactive chloro groups and an alkoxy side chain starting from 2‐chloropyrimidin‐5‐ylboronic acid and 1,3‐dibromo‐5‐butoxybenzene. The reactivity of this dielectrophile was tested by reaction with aniline and phenol, a nitrogen and oxygen nucleophile, respectively. The new dielectrophile would further provide an ideal platform for the construction of large hetero‐atom bridged macrocycles for desired properties and functions in supramolecular and material chemistry. Copyright © 2012 John Wiley & Sons, Ltd.