Biomaterial Database

One-pot synthesis of 2,4-disubstituted indoles from N-tosyl-2,3-dichloroaniline using palladium-dihydroxyterphenylphosphine catalyst. 2014

Miyuki Yamaguchi, and Kei Manabe

School of Pharmaceutical Sciences, University of Shizuoka , 52-1 Yada, Suruga-ku, Shizuoka 422-8526, Japan.

4-Chloroindoles were synthesized from readily available 2,3-dichloroaniline derivatives and terminal alkynes. The catalyst composed of palladium and dicyclohexyl(dihydroxyterphenyl)phosphine (Cy-DHTP) enabled ortho-selective Sonogashira coupling, and subsequent cyclization afforded 4-chloroindoles in high yields. This transformation was successfully applied to the one-pot synthesis of 2,4-disubstituted indoles via Suzuki-Miyaura coupling after indole formation.

UI	MeSH Term	Description	Entries
D007211	Indoles	Benzopyrroles with the nitrogen at the number one carbon adjacent to the benzyl portion, in contrast to ISOINDOLES which have the nitrogen away from the six-membered ring.
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.
D010720	Phosphines	Inorganic or organic compounds derived from phosphine (PH3) by the replacement of H atoms. (From Grant & Hackh's Chemical Dictionary, 5th ed)
D002384	Catalysis	The facilitation of a chemical reaction by material (catalyst) that is not consumed by the reaction.	Catalyses
D000814	Aniline Compounds	Compounds that include the aminobenzene structure.	Phenylamine,Phenylamines,Anilines,Compounds, Aniline
D013730	Terphenyl Compounds	Compounds consisting of benzene rings linked to each other in either ortho, meta or para positions. Permitted are any substitutions, but ring fusion to any of the benzene rings is not allowed.	Triphenyl Compounds,Compounds, Terphenyl,Compounds, Triphenyl
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