Rhodium-Catalyzed Synthesis of Imines and Esters from Benzyl Alcohols and Nitroarenes: Change in Catalyst Reactivity Depending on the Presence or Absence of the Phosphine Ligand

Taemoon Song; Ji Eun Park; Young Keun Chung

doi:10.1021/acs.joc.8b00197

Rhodium-Catalyzed Synthesis of Imines and Esters from Benzyl Alcohols and Nitroarenes: Change in Catalyst Reactivity Depending on the Presence or Absence of the Phosphine Ligand

J Org Chem. 2018 Apr 6;83(7):4197-4203. doi: 10.1021/acs.joc.8b00197. Epub 2018 Mar 19.

Authors

Taemoon Song¹, Ji Eun Park¹, Young Keun Chung¹

Affiliation

¹ Department of Chemistry, College of Natural Sciences , Seoul National University , Seoul 08826 , Korea.

PMID: 29536727
DOI: 10.1021/acs.joc.8b00197

Abstract

The [Rh(COD)Cl]₂/xantphos/Cs₂CO₃ system efficiently catalyzes the reductive N-alkylation of aryl nitro compounds with alcohols by a borrowing-hydrogen strategy to afford the corresponding imine products in good to excellent yields. In the absence of xantphos, the [Rh(COD)Cl]₂/Cs₂CO₃ catalytic system behaves as an effective catalyst for the dehydrogenative coupling of alcohols to esters, with nitrobenzene as a hydrogen acceptor. The reactivity of the rhodium catalytic system can be easily manipulated to selectively afford the imine or ester.

Publication types

Research Support, Non-U.S. Gov't