Addition of Bifunctional Organoboron Reagents to Strained Alkenes. Carbon−Carbon Bond Formation with Rh(I) Catalysis in Aqueous Media
- 21 April 2004
- journal article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 69 (10), 3478-3487
- https://doi.org/10.1021/jo049874k
Abstract
Arylboronate esters bearing a pendant Michael-type acceptor olefin undergo transmetalation with a rhodium-based catalytic complex to generate a functionalized organorhodium intermediate that can cyclize onto strained olefins in good to excellent yields. The catalytic system involves the use of an electron-rich, sterically bulky ligand to stabilize the organorhodium intermediate and reduce the incidence of protodeboronation in aqueous media.Keywords
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