Route to 3-Amidino Indoles via Pd(II)-Catalyzed C–H Bond Activation

Autor:	Jonas Rydfjord, Bobo Skillinghaug, Mats Larhed, Luke R. Odell, Peter Brandt
Rok vydání:	2017
Předmět:	Indole test C h bond 010405 organic chemistry Ligand Stereochemistry Organic Chemistry 010402 general chemistry 01 natural sciences Biochemistry 0104 chemical sciences Catalysis Amidine chemistry.chemical_compound chemistry Cyanamide Physical and Theoretical Chemistry
Zdroj:	Organic Letters. 19:4066-4069
ISSN:	1523-7052 1523-7060
DOI:	10.1021/acs.orglett.7b01836
Popis:	We report a facile synthesis of 3-amidino indoles from indoles and cyanamides. The reaction is Pd(II)-catalyzed and proceeds via C-H bond activation of the indole in its 3-position followed by a 1,2-addition of the resulting indole-palladium σ-complex to a cyanamide, which provides the corresponding amidine. The preference for 4,5-diazafluoren-9-one (DAF) as the ligand is investigated using DFT calculations, and a plausible reaction pathway is presented.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::5d198f01149e61a1bdf3f44bf4971b6c https://doi.org/10.1021/acs.orglett.7b01836 Zobrazit plný text záznamu