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

Echavarren, Antonio M.

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

Version 2 2017-11-09, 05:31

Version 1 2017-10-04, 15:20

Posted on 2017-11-09 - 05:31

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.

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Tan, Eric; Konovalov, Andrey I.; Fernández, Gabriela A.; Dorel, Ruth; Echavarren, Antonio M. (2017). Ruthenium-Catalyzed Peri- and Ortho-Alkynylation with Bromoalkynes via Insertion and Elimination. ACS Publications. Collection. https://doi.org/10.1021/acs.orglett.7b02655

https://doi.org/10.1021/acs.orglett.7b02655

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