Solvent and Base in One: Tetra‐ n ‐butylammonium Acetate as a Multi‐Purpose Ionic Liquid Medium for Ru‐Catalyzed Directed Mono‐ and Di‐ o ‐C–H Arylation Reactions | Zendy

Zou YaLing | Zendy; Wang ZhenYu | Zendy; Feng YinMao | Zendy; Li YouGui | Zendy; Kantchev Eric Assen B. | Zendy

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Solvent and Base in One: Tetra‐ n ‐butylammonium Acetate as a Multi‐Purpose Ionic Liquid Medium for Ru‐Catalyzed Directed Mono‐ and Di‐ o ‐C–H Arylation Reactions

Author(s) -

Zou YaLing,

Wang ZhenYu,

Feng YinMao,

Li YouGui,

Kantchev Eric Assen B.

Publication year - 2017

Publication title -

european journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.825

H-Index - 155

eISSN - 1099-0690

pISSN - 1434-193X

DOI - 10.1002/ejoc.201701022

Subject(s) - chemistry , ionic liquid , catalysis , acetophenone , bromide , medicinal chemistry , aryl , organic chemistry , base (topology) , solvent , imine , alkyl , mathematical analysis , mathematics

Ru‐catalyzed directed o ‐C–H arylation reactions of 2‐phenylpyridine, N ‐phenylpyrazole, acetophenone N ‐( p ‐methoxyphenyl)imine, and 2‐phenyloxazoline proceed in good to excellent yields with a number of functionalized aryl and heteroaryl bromides in neat Bu 4 NOAc at 120 °C. The acetate ion acts as the base and the relatively low melting point Bu 4 N salts (a mixture of acetate and bromide) behave as an ionic liquid. Arylation reactions of 2‐phenyloxazoline proceed with concomitant oxazolidine cleavage to give 2‐( N ‐acetylamino)ethyl benzoates promoted by side product CH 3 COOH. The dual‐purpose ionic liquid medium is compatible with both ligandless Ru for di‐arylation (optimal pre‐catalyst: RuCl 3 · x H 2 O) and Ru‐phosphane (optimal pre‐catalyst: [RuCl 2 ( p ‐cymene)] 2 /P( p ‐Tol) 3 1:4) catalysts (1–5 mol‐%) for selective mono‐arylation.

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