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.
E. Tan, A.I. Konovalov, G.A. Fernández, R. Dorel, A.M. Echavarren
Org. Lett. 2017, 19 (20), 5561-5564
DOI:
10.1021/acs.orglett.7b02655
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