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J Org Chem. 2017 May 05;82(9):4907-4917. doi: 10.1021/acs.joc.6b03089. Epub 2017 Apr 26.

A Bulky Disulfoxide Ligand for Pd-Catalyzed Oxidative Allylic C-H Amination with 2,2,2-Trichloroethyl Tosyl Carbamate.

The Journal of organic chemistry

You-Gui Li, Li Li, Ming-Yue Yang, Gang He, Eric Assen B Kantchev

Affiliations

  1. School of Chemistry and Chemical Engineering, Hefei University of Technology , 193 Tunxi Road, Hefei 230009, China.

PMID: 28421757 DOI: 10.1021/acs.joc.6b03089

Abstract

Challenging substrates and conditions in homogeneous catalysis pose stringent demands on the ligands used. A novel, bulky, 1-adamantyl-substituted disulfoxide ligand designed after a systematic evaluation of the electronic and steric properties of disulfoxide substituents permits the allylic oxidative C-N coupling reaction to proceed at lower catalyst loading while requiring a smaller excess of reagents. Additionally, this ligand improves the yields when TsNHCOOCH

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