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Widely Exploited, Yet Unreported: Regiocontrolled Synthesis and the Suzuki–Miyaura Reactions of Bromooxazole Building Blocks
Author(s) -
Solomin Vitalii V.,
Radchenko Dmytro S.,
Slobodyanyuk Evgeniy Y.,
Geraschenko Oleksandr V.,
Vashchenko Bohdan V.,
Grygorenko Oleksandr O.
Publication year - 2019
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201900032
Subject(s) - chemistry , electrophile , aryl , combinatorial chemistry , bromine , alkyl , halogenation , coupling reaction , organic chemistry , scope (computer science) , catalysis , computer science , programming language
An approach to synthesis of 2‐, 4‐, and 5‐bromooxazoles is described. The method was optimized, and its scope was extended to all three isomeric parents, as well as various alkyl‐ and aryl‐substituted bromooxazoles. It was found that direct regiocontrolled lithiation followed by reaction with electrophilic bromine source was common for all substrates and led exclusively to the target substituted 2‐, 4‐ and 5‐bromooxazoles on multigram scale. The utility of the multipurpose building blocks obtained in this work was demonstrated in the Suzuki–Miyaura cross‐coupling reaction under parallel synthesis conditions.