Silver- and Base-Enabled SOMOphilic Alkynylation of Alkylboronic Acids with Bromoalkynes

Alkynyl-containing molecules hold significant importance in organic synthesis, drug discovery, and materials science. Herein, we report an efficient protocol for the C(sp)-C(sp³) cross-coupling of bromoalkynes with primary, secondary, and tertiary alkylboronic acids. Mechanistic experiments suggest that silver and base enable the generation of an alkyl radical intermediate from the alkylboronic acid and then undergo a cascade of α-addition and β-elimination with alkynyl bromides, leading to the construction of C(sp)-C(sp³) bonds. This strategy features readily available starting materials, diverse substrates, and mild and easily handled reaction conditions.