Abstract
Borylated aryl alkynes have been synthesized via one-pot iridium catalyzed C–H borylation (CHB)/Sonogashira cross-coupling of aryl bromides. Direct borylation of aryl alkynes encountered problems related to the reactivity of the alkyne under CHB conditions. However, tolerance of aryl bromides to CHB made possible a subsequent Sonogashira cross-coupling to access the desired borylated aryl alkynes.
Highlights
Boronic acids and esters serve as precursors for a variety of functional groups and as synthetic handles for C–C bond formation [1,2]
Few tactical advances have expanded the chemoselectivity of iridium-catalyzed C–H borylation (CHB)
We art began by subjecting as alkynyl arenes to CHB conditions
Summary
Boronic acids and esters serve as precursors for a variety of functional groups and as synthetic handles for C–C bond formation [1,2]. It is likely that in these examples the presence of two bulky substituents on the alkyne hinder its reactivity, allowing for chemoselective borylation of the porphyrin moiety (1, 2) or the polyarene skeleton (3, 4). The dichotomy of these results was the first subject of our study. The preparation of borylated aromatic alkynes usually involves introduction of the boronic. The of borylated aromatic alkynesalkynes usually involves introduction of the boronic ester/acid. Wehalides hypothesized that by courtesy of CHB halogen tolerance it would be possibleit borylation of aromatic [44].
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