Biomaterial Database

Rhodium-catalyzed selective olefination of arene esters via C-H bond activation. 2011

Sae Hume Park, and Ji Young Kim, and Sukbok Chang

Department of Chemistry and Molecular-Level Interface Research Center, Korea Advanced Institute of Science and Technology, Daejeon 305-701, Korea.

A new catalytic procedure of ortho-olefination of benzoates and benzaldehydes has been developed. Ester and carboxaldehyde units were revealed to be effective chelating groups in focusing the activation of aryl C-H bonds ortho to the directing moieties under the Rh-catalyzed oxidative conditions. The reaction is highly regioselective with a range of benzoates and benzaldehydes enabling the efficient olefination with acrylates, acrylic acid, and styrenes.

UI	MeSH Term	Description	Entries
D010084	Oxidation-Reduction	A chemical reaction in which an electron is transferred from one molecule to another. The electron-donating molecule is the reducing agent or reductant; the electron-accepting molecule is the oxidizing agent or oxidant. Reducing and oxidizing agents function as conjugate reductant-oxidant pairs or redox pairs (Lehninger, Principles of Biochemistry, 1982, p471).	Redox,Oxidation Reduction
D002244	Carbon	A nonmetallic element with atomic symbol C, atomic number 6, and atomic weight [12.0096; 12.0116]. It may occur as several different allotropes including DIAMOND; CHARCOAL; and GRAPHITE; and as SOOT from incompletely burned fuel.	Carbon-12,Vitreous Carbon,Carbon 12,Carbon, Vitreous
D002384	Catalysis	The facilitation of a chemical reaction by material (catalyst) that is not consumed by the reaction.	Catalyses
D004952	Esters	Compounds derived from organic or inorganic acids in which at least one hydroxyl group is replaced by an –O-alkyl or another organic group. They can be represented by the structure formula RCOOR’ and are usually formed by the reaction between an acid and an alcohol with elimination of water.	Ester
D006859	Hydrogen	The first chemical element in the periodic table with atomic symbol H, and atomic number 1. Protium (atomic weight 1) is by far the most common hydrogen isotope. Hydrogen also exists as the stable isotope DEUTERIUM (atomic weight 2) and the radioactive isotope TRITIUM (atomic weight 3). Hydrogen forms into a diatomic molecule at room temperature and appears as a highly flammable colorless and odorless gas.	Protium,Hydrogen-1
D000475	Alkenes	Unsaturated hydrocarbons of the type Cn-H2n, indicated by the suffix -ene. (Grant & Hackh's Chemical Dictionary, 5th ed, p408)	Alkene,Olefin,Olefins,Pentene,Pentenes
D001547	Benzaldehydes	Compounds that consist of a benzene ring with a formyl group. They occur naturally in the seeds of many fruits and are used as FLAVORING AGENTS and fragrances, as well as precursors in pharmaceutical and plastics manufacturing.
D001565	Benzoates	Derivatives of BENZOIC ACID. Included under this heading are a broad variety of acid forms, salts, esters, and amides that contain the carboxybenzene structure.	Benzoate,Benzoic Acids,Acids, Benzoic
D012238	Rhodium	A hard and rare metal of the platinum group, atomic number 45, atomic weight 102.905, symbol Rh.	Rhodium-103,Rhodium 103
D015394	Molecular Structure	The location of the atoms, groups or ions relative to one another in a molecule, as well as the number, type and location of covalent bonds.	Structure, Molecular,Molecular Structures,Structures, Molecular