Open AccessRuthenium-Catalyzed Peri- and Ortho-Alkynylation with Bromoalkynes via Insertion and Elimination
Author(s) -
Eric Tan,
А. И. Коновалов,
Gabriela Araceli Fernández,
Ruth Dorel,
Antonio M. Echavarren
Publication year - 2017
Publication title -
organic letters
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.94
H-Index - 239
eISSN - 1523-7060
pISSN - 1523-7052
DOI - 10.1021/acs.orglett.7b02655
Subject(s) - chemistry , alkynylation , metalation , catalysis , ruthenium , medicinal chemistry , bromide , functional group , alkyne , group (periodic table) , organic chemistry , polymer
The alkynylation of naphthols takes place with total regiocontrol at the peri position of the hydroxyl group in the presence of [RuCl 2 (p-cymene)] 2 as the catalyst. This reaction features high functional group tolerance. The related ortho-alkynylation of benzoic acids proceeds under similar conditions and also shows wide functional group tolerance. Both reactions proceed through metalation, insertion of the alkyne, and bromide elimination.