Brønsted Acid-Mediated Hydrative Arylation of Unactivated Alkynes

Daniel Kaiser; Luís F Veiros; Nuno Maulide

doi:10.1002/chem.201600432

Brønsted Acid-Mediated Hydrative Arylation of Unactivated Alkynes

Chemistry. 2016 Mar 24;22(14):4727-32. doi: 10.1002/chem.201600432. Epub 2016 Feb 25.

Authors

Daniel Kaiser¹, Luís F Veiros², Nuno Maulide³

Affiliations

¹ Faculty of Chemistry, Institute of Organic Chemistry, University of Vienna, Währinger Strasse 38, 1090, Vienna, Austria.
² Centro de Química Estrutural, Instituto Superior Técnico, Universidade de Lisboa, Av. Rovisco Pais 1, 1049-001, Lisboa, Portugal.
³ Faculty of Chemistry, Institute of Organic Chemistry, University of Vienna, Währinger Strasse 38, 1090, Vienna, Austria. nuno.maulide@univie.ac.at.

PMID: 26918863
DOI: 10.1002/chem.201600432

Abstract

The Brønsted acid-mediated reaction of unactivated alkynes with aryl sulfoxides leads to simultaneous hydration and intermolecular C-C bond formation. This solvent- and metal-free transformation directly delivers α-arylated carbonyl compounds as the products of a formal hydrative arylation in an atom-economical manner. The products bear useful synthetic handles for further functionalization.

Keywords: alkynes; arylation; organic chemistry; rearrangement; sulfoxides.

Publication types

Research Support, Non-U.S. Gov't