Biomaterial Database

Palladium-catalyzed carbonylation of aryl tosylates and mesylates. 2008

Rachel H Munday, and Joseph R Martinelli, and Stephen L Buchwald

Department of Chemistry, Room 18-490, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, USA.

A general protocol for the palladium-catalyzed carbonylation of aryl tosylates and mesylates to form esters has been developed using a catalyst system derived from Pd(OAc)2 and the bulky, bidentate dcpp ligand. The system operates under mild conditions: atmospheric CO pressure and temperatures of 80-110 degrees C. A broad substrate scope has been demonstrated allowing carbonylation of electron-rich, electron-poor, and heterocyclic tosylates and mesylates, and the reaction shows wide functional group tolerance.

UI	MeSH Term	Description	Entries
D008024	Ligands	A molecule that binds to another molecule, used especially to refer to a small molecule that binds specifically to a larger molecule, e.g., an antigen binding to an antibody, a hormone or neurotransmitter binding to a receptor, or a substrate or allosteric effector binding to an enzyme. Ligands are also molecules that donate or accept a pair of electrons to form a coordinate covalent bond with the central metal atom of a coordination complex. (From Dorland, 27th ed)	Ligand
D008698	Mesylates	Organic salts or esters of methanesulfonic acid.	Mesilate,Methanesulfonates,Mesilates,Mesylate,Methylenesulfonates
D009942	Organometallic Compounds	A class of compounds of the type R-M, where a C atom is joined directly to any other element except H, C, N, O, F, Cl, Br, I, or At. (Grant & Hackh's Chemical Dictionary, 5th ed)	Metallo-Organic Compound,Metallo-Organic Compounds,Metalloorganic Compound,Organometallic Compound,Metalloorganic Compounds,Compound, Metallo-Organic,Compound, Metalloorganic,Compound, Organometallic,Compounds, Metallo-Organic,Compounds, Metalloorganic,Compounds, Organometallic,Metallo Organic Compound,Metallo Organic Compounds
D010165	Palladium	A chemical element having an atomic weight of 106.4, atomic number of 46, and the symbol Pd. It is a white, ductile metal resembling platinum, and following it in abundance and importance of applications. It is used in dentistry in the form of gold, silver, and copper alloys.
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
D000438	Alcohols	Alkyl compounds containing a hydroxyl group. They are classified according to relation of the carbon atom: primary alcohols, R-CH2OH; secondary alcohols, R2-CHOH; tertiary alcohols, R3-COH. (From Grant & Hackh's Chemical Dictionary, 5th ed)
D013237	Stereoisomerism	The phenomenon whereby compounds whose molecules have the same number and kind of atoms and the same atomic arrangement, but differ in their spatial relationships. (From McGraw-Hill Dictionary of Scientific and Technical Terms, 5th ed)	Molecular Stereochemistry,Stereoisomers,Stereochemistry, Molecular,Stereoisomer
D014105	Tosyl Compounds	Toluenesulfonyl compounds with general formula CH3C6H4S(O2)R” widely used to block amino groups in the course of syntheses of drugs and other biologically active compounds.	Toluenesulfonyl Compounds,Compounds, Toluenesulfonyl,Compounds, Tosyl
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