Prev. Article Next Article Table of Contents

Article

Rhodium-Catalyzed Tandem Cyclization: Formation of 1H-Indenes and 1-Alkylideneindans from Arylboronate Esters in Aqueous Media

Supporting Info

Mark Lautens* and Tzvetelina Marquardt

Davenport Chemical Laboratories, Department of Chemistry, University of Toronto, 80 St. George Street, Toronto, Ontario M5S 3H6, Canada

J. Org. Chem., 2004, 69 (14), pp 4607–4614

DOI: 10.1021/jo049722p

Publication Date (Web): June 11, 2004

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, mlautens@chem.utoronto.ca

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.

View: Full Text HTML | Hi-Res PDF

Tools

SciFinder Links

History

Published In Issue July 09, 2004
Received February 16, 2004

Recommend & Share

Related Content

Addition of Bifunctional Organoboron Reagents to Strained Alkenes. Carbon−Carbon Bond Formation with Rh(I) Catalysis in Aqueous MediaThe Journal of Organic Chemistry
- Addition of Bifunctional Organoboron Reagents to Strained Alkenes. Carbon−Carbon Bond Formation with Rh(I) Catalysis in Aqueous Media
  Mark Lautens and John Mancuso
  The Journal of Organic Chemistry 2004 69 (10), pp 3478–3487
  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. ...
  Abstract | Full Text HTML | Hi-Res PDF
Iridium-Catalyzed Addition of Acid Chlorides to Terminal AlkynesJournal of the American Chemical Society
- Iridium-Catalyzed Addition of Acid Chlorides to Terminal Alkynes
  Tomohiro Iwai, Tetsuaki Fujihara, Jun Terao and Yasushi Tsuji
  Journal of the American Chemical Society 2009 131 (19), pp 6668–6669
  Abstract: An iridium N-heterocyclic carbene (NHC) complex, IrCl(cod)(IPr), successfully catalyzed an addition of common aromatic acid chlorides to terminal alkynes to afford (Z)-β-chloro-α,β-unsaturated ketones regio- and stereoselectively. When the NHC ligand (IPr)...
  Abstract | Full Text HTML | PDF w/ Links | Hi-Res PDF
Diastereoselective Formation of Indanes from Arylboronate Esters Catalyzed by Rhodium(I) in Aqueous MediaOrganic Letters
- Diastereoselective Formation of Indanes from Arylboronate Esters Catalyzed by Rhodium(I) in Aqueous Media
  Mark Lautens and John Mancuso
  Organic Letters 2002 4 (12), pp 2105–2108
  Abstract: Arylboronate esters bearing a pendant Michael-acceptor alkene can add to norbornene and cyclize to give indane systems in yields ranging from 62% to 95% with high diastereomeric excess (>20:1). The reaction is performed in an organic/aqueous emulsion and ...
  Abstract | Full Text HTML | Hi-Res PDF

Article

Rhodium-Catalyzed Tandem Cyclization: Formation of 1H-Indenes and 1-Alkylideneindans from Arylboronate Esters in Aqueous Media

Abstract

Tools

SciFinder Links

History

Recommend & Share

Related Content

Addition of Bifunctional Organoboron Reagents to Strained Alkenes. Carbon−Carbon Bond Formation with Rh(I) Catalysis in Aqueous Media

Iridium-Catalyzed Addition of Acid Chlorides to Terminal Alkynes

Diastereoselective Formation of Indanes from Arylboronate Esters Catalyzed by Rhodium(I) in Aqueous Media

Other ACS content by these authors:

JOURNALS

BOOKS

MAGAZINE

COMMUNITIES

DIRECTORIES & DATABASES