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Rhodium-catalyzed tandem cyclization: formation of 1H-indenes and 1-alkylideneindans from arylboronate esters in aqueous media.

Authors
  • Lautens, Mark
  • Marquardt, Tzvetelina
Type
Published Article
Journal
The Journal of organic chemistry
Publication Date
Jul 09, 2004
Volume
69
Issue
14
Pages
4607–4614
Identifiers
PMID: 15230582
Source
Medline
License
Unknown

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.

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