Carboxylate-Enhanced Rhodium(III)-Catalyzed Aryl C–H Alkylation with Conjugated Alkenes under Mild Conditions

 

 

Zhao Zhang^†§, Mengyao Tang^†§, Shengnan Han^†, Lutz Ackermann^‡, and Jie Li^*†

^† School of Pharmaceutical Sciences, Jiangnan University, Lihu Road 1800, 214122 Wuxi, P.R. China

^‡ Institut für Organische und Biomolekulare Chemie, Georg-August-Universität Göttingen, Tammannstrasse 2, 37077 Göttingen, Germany

J. Org. Chem., Article ASAP

DOI: 10.1021/acs.joc.6b02672

Publication Date (Web): December 2, 2016

Copyright © 2016 American Chemical Society

*E-mail: jjackli@jiangnan.edu.cn.

Abstract

 

 

 

 

Rhodium(III)-catalyzed C–H bond functionalization for the synthesis of β-aryl aldehydes and ketones from (hetero)aryl oximes, pyri(mi)dine, as well as pyrazoles and α,β-unsaturated carbonyl compounds has been developed under exceedingly mild reaction conditions. Thus, the versatile rhodium(III) catalysis features high step- and atom-economy, oxidant-free reaction conditions, and broad substrate scope.

Supporting Information

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The Supporting Information is available free of charge on the ACS Publications website at DOI: 10.1021/acs.joc.6b02672.

• Characterization of new compounds (¹H, ¹³C, ¹⁹F NMR and NOESY spectra) and mechanistic studies (KIE experiments, etc.) (PDF)

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