Back to Search
Start Over
5-Norbornene-2-carboxylic acid: Another catalytic mediator for Catellani-type reactions
- Source :
- Tetrahedron. 75:1774-1780
- Publication Year :
- 2019
- Publisher :
- Elsevier BV, 2019.
-
Abstract
- Mediators play a central role in Catellani-type reactions. Herein we reported the discovery of inexpensive 5-norbornene-2-carboxylic acid (N4) as a general catalytic mediator (20 mol%) to facilitate ortho C–H activation and the following C–C bond formation of aryl iodides. Firstly, a cooperative catalytic system comprising N4 and a palladium/XPhos complex was developed for the novel Catellani/redox-relay Heck cascade to construct tetrahydronaphthalenes and indanes that contain a quaternary carbon stereogenic center. The striking feature of this work was the avoidance of stoichiometric NBE mediator that are usually required for Catellani-type reactions. Then, preliminary results demonstrated that N4 could act as a general catalytic mediator to replace NBE for other Catellani-type reactions, which will undoubtedly inspire future developments in the field of cooperative catalysis. Finally, control experiments indicated that the carboxylic acid moiety of N4 plays an essential role in its ability to serve as a superior mediator.
- Subjects :
- chemistry.chemical_classification
010405 organic chemistry
Chemistry
Carboxylic acid
Aryl
Organic Chemistry
chemistry.chemical_element
010402 general chemistry
01 natural sciences
Biochemistry
Combinatorial chemistry
0104 chemical sciences
Catalysis
Stereocenter
chemistry.chemical_compound
XPhos
Drug Discovery
Moiety
Norbornene
Palladium
Subjects
Details
- ISSN :
- 00404020
- Volume :
- 75
- Database :
- OpenAIRE
- Journal :
- Tetrahedron
- Accession number :
- edsair.doi...........d5292c7089ef000a9c41816b1c1da17f