Formal regiocontrolled hydroboration of unbiased internal alkynes via borylation/allylic alkylation of terminal alkynes.

Autor: Moure AL; Departamento de Química Orgánica, Facultad de Ciencias, Universidad Autónoma de Madrid (UAM), Cantoblanco, 28049 Madrid, Spain., Mauleón P, Gómez Arrayás R, Carretero JC
Jazyk: angličtina
Zdroj: Organic letters [Org Lett] 2013 Apr 19; Vol. 15 (8), pp. 2054-7. Date of Electronic Publication: 2013 Apr 09.
DOI: 10.1021/ol4007663
Abstrakt: 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.
Databáze: MEDLINE