Abstract
Control of boronic acid solution speciation is presented as a new strategy for the chemoselective synthesis of boronic esters. Manipulation of the solution equilibria within a cross-coupling milieu enables the formal homologation of aryl and alkenyl boronic acid pinacol esters. The generation of a new, reactive boronic ester in the presence of an active palladium catalyst also facilitates streamlined iterative catalytic C=C bond formation and provides a method for the controlled oligomerization of sp2-hybridized boronic esters.
Highlights
Control of boronic acid solution speciation is presented as a new strategy for the chemoselective synthesis of boronic esters
Common methods for the preparation of sp2 boronic acid pinacol (BPin) esters generally rely upon the stoichiometric manipulation of a single boron species (Figure 1 a)
Chemoselective synthesis of a boronic ester based on the control of speciation is a concept that would represent a fundamental advance in the field and
Summary
Control of boronic acid solution speciation is presented as a new strategy for the chemoselective synthesis of boronic esters. We show that controlling the solution equilibria of boronic acid pinacol (BPin) and N-methyliminodiacetic acid (BMIDA) esters[7] during the course of a Suzuki–Miyaura cross-coupling event enables chemoselective formal homologation[8] of BPin esters (Figure 1 b).
Sign-in/Register to view highlights & summary Sign-in/Register to access full text options 
Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Schedule a callDisclaimer: All third-party content on this website/platform is and will remain the property of their respective owners and is provided on "as is" basis without any warranties, express or implied. Use of third-party content does not indicate any affiliation, sponsorship with or endorsement by them. Any references to third-party content is to identify the corresponding services and shall be considered fair use under The CopyrightLaw.
