Addition of Bifunctional Organoboron Reagents to Strained Alkenes. Carbon−Carbon Bond Formation with Rh(I) Catalysis in Aqueous Media
- 21 April 2004
- journal article
- research 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
This publication has 36 references indexed in Scilit:
- Merry-Go-Round Multiple Alkylation on Aromatic Rings via Rhodium CatalysisJournal of the American Chemical Society, 2000
- Synthesis of Water-Soluble, Aliphatic Phosphines and Their Application to Well-Defined Ruthenium Olefin Metathesis CatalystsOrganometallics, 1996
- A Simple and Convenient Preparation of [(Ph3P)4Rh2(.mu.-OH)2] and Its Reactions with C-H, O-H, and M-H AcidsOrganometallics, 1995
- The Atom Economy—A Search for Synthetic EfficiencyScience, 1991
- The Palladium‐Catalyzed Cross‐Coupling Reactions of Organotin Reagents with Organic Electrophiles [New Synthetic Methods (58)]Angewandte Chemie International Edition in English, 1986
- Carbon-carbon bond formation promoted by transition metal carbonyls. 19. General synthesis of tropane alkaloids via the polybromo ketone-iron carbonyl reactionJournal of the American Chemical Society, 1978
- Electrophilic Displacement Reactions. XVI. Metal Ion Catalysis in the Protodeboronation of Areneboronic Acids1-3Journal of the American Chemical Society, 1964
- Electrophilic Displacement Reactions. XII. Substituent Effects in the Protodeboronation of Areneboronic Acids1-3Journal of the American Chemical Society, 1961
- Electrophilic Displacement Reactions. XI. Solvent Isotope Effects in the Protodeboronation of Areneboronic Acids1-3Journal of the American Chemical Society, 1961
- Electrophilic Displacement Reactions. X. General Acid Catalysis in the Protodeboronation of Areneboronic Acids1-3Journal of the American Chemical Society, 1961