Design and Applications of a SO2 Surrogate in Palladium‐Catalyzed Direct Aminosulfonylation between Aryl Iodides and Amines
Authors:
- 24 December 2020
- journal article
- research article
- Published by Wiley in Angewandte Chemie
- Vol. 133 (13) , 7429-7435
Abstract
A new SO2 surrogate is reported that is cheap, bench‐stable, and can be accessed in just two steps from bulk chemicals. Essentially complete SO2 release is achieved in 5 minutes. Eight established sulfonylation reactions proceeded smoothly by ex situ formation of SO2 by utilizing a two‐chamber system in combination with the SO2 surrogate. Furthermore, we report the first direct aminosulfonylation between aryl iodides and amines. Broad functional group tolerance is demonstrated, and the method is applicable to pharmaceutically relevant substrates, including heterocyclic substrates.Keywords
Funding Information
- National Natural Science Foundation of China (21901168)
- Lundbeck Foundation (R250-2017-1292)
- Danmarks Grundforskningsfond (DNRF118)
- NordForsk (85378)
This publication has 84 references indexed in Scilit:
- DABCO-Bis(sulfur dioxide), DABSO, as a Convenient Source of Sulfur Dioxide for Organic Synthesis: Utility in Sulfonamide and Sulfamide PreparationOrganic Letters, 2011
- Ex SituGeneration of Stoichiometric and Substoichiometric12CO and13CO and Its Efficient Incorporation in Palladium Catalyzed AminocarbonylationsJournal of the American Chemical Society, 2011
- Palladium-Catalyzed Aminosulfonylation of Aryl HalidesJournal of the American Chemical Society, 2010
- Direct Conversion of Thiols to Sulfonyl Chlorides and SulfonamidesThe Journal of Organic Chemistry, 2009
- Aqueous Process Chemistry: The Preparation of Aryl Sulfonyl ChloridesOrganic Process Research & Development, 2009
- Expanding the Diversity of Polycyclic Aromatics Through a Suzuki–Miyaura Cross‐Coupling StrategyEuropean Journal of Organic Chemistry, 2007
- Synthesis of Symmetrical Sulfones from Rongalite: Expansion to Cyclic Sulfones by Ring‐Closing MetathesisEuropean Journal of Organic Chemistry, 2005
- Structure-Based Design: Synthesis and Biological Evaluation of a Series of Novel Cycloamide-Derived HIV-1 Protease InhibitorsJournal of Medicinal Chemistry, 2005
- Annulations with tetrachlorothiophene 1,1-dioxideThe Journal of Organic Chemistry, 1980
- Sulfamoylbenzoic acid ester derivatives as potential local anesthetics. IJournal of Medicinal Chemistry, 1969