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Speciation Control During Suzuki–Miyaura Cross‐Coupling of Haloaryl and Haloalkenyl MIDA Boronic Esters
Author(s) -
Fyfe James W. B.,
Valverde Elena,
Seath Ciaran P.,
Kennedy Alan R.,
Redmond Joanna M.,
Anderson Niall A.,
Watson Allan J. B.
Publication year - 2015
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201500970
Subject(s) - pinacol , boronic acid , phenylboronic acid , chemistry , adduct , suzuki reaction , coupling (piping) , combinatorial chemistry , organic chemistry , catalysis , palladium , materials science , metallurgy
Abstract Boronic acid solution speciation can be controlled during the Suzuki–Miyaura cross‐coupling of haloaryl N ‐methyliminodiacetic acid (MIDA) boronic esters to enable the formal homologation of boronic acid derivatives. The reaction is contingent upon control of the basic biphase and is thermodynamically driven: temperature control provides highly chemoselective access to either BMIDA adducts at room temperature or boronic acid pinacol ester (BPin) products at elevated temperature. Control experiments and solubility analyses have provided some insight into the mechanistic operation of the formal homologation process.