Ohmic Heating-Assisted Synthesis of 3-Arylquinolin-4(1H)-ones by a Reusable and Ligand-Free Suzuki-Miyaura Reaction in Water

• Type: Article in International Scientific Journal
• Date: 2015

Authors

Pinto, J (Author) Other; Silva, VLM (Author) Other; Silva, AMG (Author) REIT; Luis M N B F Santos (Author) FCUP; Silva, AMS (Author) Other

Journal

Title: Journal of Organic Chemistry

Vol. 80

Pages: 6649-6659

ISSN: 0022-3263

Publisher: American Chemical Society

Indexing

ISI Web of Knowledge - 25 Citations

Scopus - 27 Citations

Other information

Authenticus ID: P-00G-DXS

DOI: 10.1021/acs.joc.5b00793

Abstract (EN): Potential bioactive 3-arylquinolin-4(1H)-ones were synthesized under ohmic heating using an efficient, reusable, and ligand-free protocol developed for the Suzuki-Miyaura coupling of 1-substituted-3-iodoquinolin-4(1H)-ones with several boronic acids in water using Pd(OAc)(2) as a catalyst and tetrabutylammonium bromide (TBAB) as the phase transfer catalyst. Good substrate generality, ease of execution, short reaction time, and practicability make this method exploitable for the generation of libraries of B ring-substituted 3-arylquinolin-4(1H)-ones. After a simple workup, the Pd/catalyst-H2O-TBAB system could be reused for at least seven cycles without significant loss of activity.

Language: English

Type (Professor's evaluation): Scientific

No. of pages: 11