Synthesis of Calix[4]arene Triflates and Their Unusual Chemical Reactivity in Palladium-Catalyzed Reactions
- 3 May 2000
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 65 (11) , 3299-3302
- https://doi.org/10.1021/jo000003u
Abstract
The formation of p-tert-butylcalix[4]arene mono-, bis-, tris-, and tetrakistriflates 3, 2, 4, and 5, respectively, and their respective reactions, under typical Pd-catalyzed carbonylative, Suzuki−Miyaura coupling, or deoxygenation conditions are described. A novel, nonsolvent-derived 1:1 clathrate (6) of benzophenone and 3 was formed from the palladium-catalyzed carbonylative reaction of phenylboronic acid and 2. The X-ray crystal structure of this first nonsolvent-derived clathrate of a calix[4]arene derivative is reported. Another 1:1 clathrate of triethylamine and 3 was formed during the attempted Pd-catalyzed deoxygenation of 2.Keywords
This publication has 10 references indexed in Scilit:
- Synthetic and NMR Studies on Calix[n]Arene (n = 4,6,8) Triflates, Mesylates, and TosylatesSupramolecular Chemistry, 1998
- Calixarenes RevisitedPublished by Royal Society of Chemistry (RSC) ,1998
- Palladium-Catalyzed Carbonylative Cross-Coupling Reaction of Arylboronic Acids with Aryl Electrophiles: Synthesis of Biaryl KetonesThe Journal of Organic Chemistry, 1998
- Preparation and Conformation of Monohalotetrahydroxycalix[5]arenesThe Journal of Organic Chemistry, 1996
- Palladium-Catalyzed Cross-Coupling Reactions of Organoboron CompoundsChemical Reviews, 1995
- Inclusion of ions and neutral molecules in calixarenesPublished by Oxford University Press (OUP) ,1991
- Calixarenes. 20. The interaction of calixarenes and aminesJournal of the American Chemical Society, 1987
- The Palladium‐Catalyzed Cross‐Coupling Reactions of Organotin Reagents with Organic Electrophiles [New Synthetic Methods (58)]Angewandte Chemie International Edition in English, 1986
- Proposed structure of heme d, a prosthetic group of bacterial terminal oxidasesJournal of the American Chemical Society, 1985
- Molecular inclusion in functionalized macrocycles 4.the crystal and molecular structure of the cyclo {tetrakis[(5-t-butyl-2-acetoxy-1,3-phenylene)methylene]}-acetic acid (1:1) clathrateJournal of Molecular Structure, 1982