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

Eric Tan | Zendy; Andrey I. Konovalov | Zendy; Gabriela A. Fernández | Zendy; Ruth Dorel | Zendy; Antonio M. Echavarren | Zendy

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

Author(s) -

Eric Tan,

Andrey I. Konovalov,

Gabriela A. 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 , ruthenium , catalysis , alkynylation , peri , combinatorial chemistry , medicinal chemistry , organic chemistry , philosophy , theology

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.

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