Rhodium-Catalyzed Tandem Cyclization: Formation of 1H-Indenes and 1-Alkylideneindans from Arylboronate Esters in Aqueous Media
- 11 June 2004
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 69 (14), 4607-4614
- https://doi.org/10.1021/jo049722p
Abstract
Arylboronate esters bearing a pendant Michael-type acceptor olefin or acetylene linkage undergo transmetalation with a rhodium-based catalytic complex to generate a functionalized organorhodium intermediate which can cyclize onto nonterminal acetylenes in good to excellent yields. The catalytic system involves the use of electron-rich, sterically bulky ligands as tri-tert-butylphosphonium tetrafluoroborate stabilizing the organorhodium intermediates and reduces the incidence of protodeboronation in aqueous media.Keywords
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