BIOMAT Database Logo BIOMAT Database Logo

Pd(II)-catalyzed ortho- or meta-C-H olefination of phenol derivatives. 2013

Hui-Xiong Dai, and Gang Li, and Xing-Guo Zhang, and Antonia F Stepan, and Jin-Quan Yu
Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, USA.

A combination of weakly coordinating auxiliaries and ligand acceleration allows for the development of both ortho- and meta-selective C-H olefination of phenol derivatives. These reactions demonstrate the feasibility of directing C-H functionalizations when functional groups are distal to target C-H bonds. The meta-C-H functionalization of electron-rich phenol derivatives is unprecedented and orthogonal to previous electrophilic substitution of phenols in terms of regioselectivity. These methods are also applied to functionalize α-phenoxyacetic acids, a fibrate class of drug scaffolds.

UI MeSH Term Description Entries
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.
D010636 Phenols Benzene derivatives that include one or more hydroxyl groups attached to the ring structure.
D002384 Catalysis The facilitation of a chemical reaction by material (catalyst) that is not consumed by the reaction. Catalyses
D000085 Acetates Derivatives of ACETIC ACID. Included under this heading are a broad variety of acid forms, salts, esters, and amides that contain the carboxymethane structure. Acetate,Acetic Acid Esters,Acetic Acids,Acids, Acetic,Esters, Acetic Acid
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
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

Related Publications

Hui-Xiong Dai, and Gang Li, and Xing-Guo Zhang, and Antonia F Stepan, and Jin-Quan Yu
Rhodium-catalyzed direct ortho C-H olefination of phenol derivatives.
October 2011, Chemical communications (Cambridge, England),
Hui-Xiong Dai, and Gang Li, and Xing-Guo Zhang, and Antonia F Stepan, and Jin-Quan Yu
Pd(II)-Catalyzed ortho-C-H Olefination/Dearomatization of N-Aryl Ureas: An Approach to Imine Derivatives.
March 2016, Organic letters,
Hui-Xiong Dai, and Gang Li, and Xing-Guo Zhang, and Antonia F Stepan, and Jin-Quan Yu
Pd(II)-catalyzed olefination of sp3 C-H bonds.
March 2010, Journal of the American Chemical Society,
Hui-Xiong Dai, and Gang Li, and Xing-Guo Zhang, and Antonia F Stepan, and Jin-Quan Yu
Pd(II)-catalyzed enantioselective C-H olefination of diphenylacetic acids.
January 2010, Journal of the American Chemical Society,
Hui-Xiong Dai, and Gang Li, and Xing-Guo Zhang, and Antonia F Stepan, and Jin-Quan Yu
Pd-catalyzed directed ortho-C-H alkenylation of phenylalanine derivatives.
March 2015, The Journal of organic chemistry,
Hui-Xiong Dai, and Gang Li, and Xing-Guo Zhang, and Antonia F Stepan, and Jin-Quan Yu
Pd(ii)-catalyzed remote regiodivergent ortho- and meta-C-H functionalizations of phenylethylamines.
October 2015, Chemical science,
Hui-Xiong Dai, and Gang Li, and Xing-Guo Zhang, and Antonia F Stepan, and Jin-Quan Yu
Pd(II)-catalyzed ortho-C-H oxidation of arylacetic acid derivatives: synthesis of benzofuranones.
February 2014, Organic letters,
Hui-Xiong Dai, and Gang Li, and Xing-Guo Zhang, and Antonia F Stepan, and Jin-Quan Yu
Ruthenium(II)-Catalyzed Regioselective Ortho C-H Allenylation of Electron-Rich Aniline and Phenol Derivatives.
February 2020, The Journal of organic chemistry,
Hui-Xiong Dai, and Gang Li, and Xing-Guo Zhang, and Antonia F Stepan, and Jin-Quan Yu
Ortho arylation of acetanilides via Pd(II)-catalyzed C-H functionalization.
May 2007, Journal of the American Chemical Society,
Hui-Xiong Dai, and Gang Li, and Xing-Guo Zhang, and Antonia F Stepan, and Jin-Quan Yu
Ruthenium-Catalyzed Meta-Selective C-H Difluoromethylation of Phenol Derivatives.
November 2020, The Journal of organic chemistry,
Copied contents to your clipboard!