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Formal Regiocontrolled Hydroboration of Unbiased Internal Alkynes via Borylation/Allylic Alkylation of Terminal Alkynes

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journal contribution
posted on 2013-04-19, 00:00 authored by Abraham L. Moure, Pablo Mauleón, Ramón Gómez Arrayás, Juan Carlos Carretero
In accessing trisubstituted vinyl boronates from terminal alkynes, a propargyl directing (2-pyridyl)sulfonyl group allows terminal alkynes to undergo Cu-catalyzed B2(pin)2-borylation and subsequent Cu-catalyzed allylic alkylation with Grignard reagents without affecting the pinacolboronate moiety, thereby formally enabling a highly stereo- and regiocontrolled access to hydroboration products of unbiased dialkyl internal alkynes.