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

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 oxidati...

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Bibliographic Details
Published in:Journal of organic chemistry 2017-05, Vol.82 (9), p.4907-4917
Main Authors: Li, You-Gui, Li, Li, Yang, Ming-Yue, He, Gang, Kantchev, Eric Assen B
Format: Article
Language:English
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Summary: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 TsNHCOOCH2CCl3, a novel reagent that permits deprotection of the products under both acidic and basic conditions, is used.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.6b03089