Mild and selective base-free C–H arylation of heteroarenes

Autor:	Franziska Schoenebeck, Timothy Noël, Nico Erdmann, Indrek Kalvet, Alexander V. Nyuchev, Hannes P. L. Gemoets, Volker Hessel
Přispěvatelé:	Micro Flow Chemistry and Synthetic Meth.
Jazyk:	angličtina
Rok vydání:	2016
Předmět:	010405 organic chemistry Chemistry Base free Substrate (chemistry) chemistry.chemical_element General Chemistry 010402 general chemistry 01 natural sciences 0104 chemical sciences 3. Good health Reagent ddc:540 Organic chemistry Selectivity Palladium
Zdroj:	Chemical science 8(2), 1046-1055 (2017). doi:10.1039/C6SC02595A Chemical Science, 2017(2):8, 1046-1055. Royal Society of Chemistry
ISSN:	2041-6520
DOI:	10.1039/c6sc02595a
Popis:	A mild and selective C–H arylation strategy for indoles, benzofurans and benzothiophenes is described. The arylation method engages aryldiazonium salts as arylating reagents in equimolar amounts. The protocol is operationally simple, base free, moisture tolerant and air tolerant. It utilizes low palladium loadings (0.5 to 2.0 mol% Pd), short reaction times, green solvents (EtOAc/2-MeTHF or MeOH) and is carried out at room temperature, providing a broad substrate scope (47 examples) and excellent selectivity (C-2 arylation for indoles and benzofurans, C-3 arylation for benzothiophenes). Mechanistic experiments and DFT calculations support a Heck–Matsuda type coupling mechanism.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::370cf1d1af949a97b4aa2f30fb4b2c0c https://doi.org/10.1039/c6sc02595a Zobrazit plný text záznamu