Palladium-Catalyzed Multi-Component Reactions of N-Tosylhydrazones, 2-Iodoanilines and CO2 towards 4-Aryl-2-Quinolinones

Song Sun; Wei-Ming Hu; Ning Gu; Jiang Cheng

doi:10.1002/chem.201604256

Palladium-Catalyzed Multi-Component Reactions of N-Tosylhydrazones, 2-Iodoanilines and CO₂ towards 4-Aryl-2-Quinolinones

Chemistry. 2016 Dec 23;22(52):18729-18732. doi: 10.1002/chem.201604256. Epub 2016 Nov 17.

Authors

Song Sun¹, Wei-Ming Hu¹, Ning Gu¹, Jiang Cheng¹

Affiliation

¹ School of Petrochemical Engineering, Jiangsu Key Laboratory of Advanced Catalytic Materials & Technology, and Jiangsu Province Key Laboratory of Fine Petrochemical Engineering, Changzhou University, Gehu Road 1, Changzhou, 213164, P. R. China.

PMID: 27785839
DOI: 10.1002/chem.201604256

Abstract

A palladium-catalyzed three-component reaction between N-tosylhydrazones, 2-iodoanilines and atmospheric pressure CO₂ was developed whereby a tandem carbene migration insertion/lactamization strategy afforded 4-aryl-2-quinolinones in moderate to good yields. Notably, a wide range of functional groups were tolerated in this procedure. This protocol features the simultaneous formation of four novel bonds; two C-C, one C=C and one C-N (amide), representing an efficient methodology for incorporation of CO₂ into heterocycles.

Keywords: 4-aryl-2-quinolinone; N-tosylhydrazone; carbon dioxide fixation; heterocycles; multi-component reaction.