Ruthenium-Catalyzed Peri- and Ortho-Alkynylation with Bromoalkynes via Insertion and Elimination

• DOI: 10.1021/acs.orglett.7b02655
• Publication Date: 2017-10-04T15:37:12Z
• Authors: Eric Tan; Andrey I. Konovalov; Gabriela A. Ferná...; Ruth Dorel; Antonio M. Echava...
• Keywords: Naphtols; Ruthenium catalyst; Benzoic acids; https://purl.org/becyt/ford/1.4; Alkynylation; https://purl.org/becyt/ford/1; 54; 01 natural sciences; 0104 chemical sciences

The alkynylation of naphthols takes place with total regiocontrol at the peri position of the hydroxyl group in the presence of [RuCl2(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.