Direct Synthesis of N‐Acyl Sulfonimidamides and N‐Sulfonimidoyl Amidines from Sulfonimidoyl Azides
- 15 May 2018
- journal article
- research article
- Published by Wiley in Advanced Synthesis & Catalysis
- Vol. 360 (13) , 2465-2469
Abstract
Herein, we describe the preparation of sulfonimidoyl azides, and demonstrate their utility in the construction of N‐acyl sulfonimidamides and N‐sulfonimidoyl amidines. N‐Acyl sulfonimidamides were synthesized in good to very good yields via “on water” copper‐catalyzed three‐component coupling between sulfonimidoyl azide, alkynes and water. The use of amines as nucleophiles yielded a wide range of N‐sulfonimidoyl amidines. Both reactions were completed in very short time at room temperature under mild conditions, thus establishing the potential of sulfonimidoyl azides, the aza‐analogues of sulfonyl azides, as an excellent precursor to derive functionalized sulfonimidamides in one step. magnified imageKeywords
Funding Information
- DST-INSPIRE (GAP-135739)
This publication has 32 references indexed in Scilit:
- Synthesis of Novel Aryl and Heteroaryl Acyl Sulfonimidamides via Pd-Catalyzed Carbonylation Using a Nongaseous PrecursorOrganic Letters, 2013
- Efficient Synthesis of 1-Sulfonyl-1,2,3-triazolesOrganic Letters, 2010
- Catalytic stereoselective alkene aziridination with sulfonimidamidesTetrahedron: Asymmetry, 2010
- Synthesis of Amino-Functionalized Sulfonimidamides and Their Application in the Enantioselective Henry ReactionThe Journal of Organic Chemistry, 2010
- Synthesis of Enantiopure Sulfonimidamides and Elucidation of Their Absolute Configuration by Comparison of Measured and Calculated CD Spectra and X‐Ray Crystal Structure DeterminationChemistry – A European Journal, 2009
- Toward a Synthetically Useful Stereoselective C−H Amination of HydrocarbonsJournal of the American Chemical Society, 2007
- Efficient Diastereoselective Intermolecular Rhodium‐Catalyzed C-H AminationAngewandte Chemie International Edition, 2006
- Efficient Diastereoselective Intermolecular Rhodium‐Catalyzed C-H AminationAngewandte Chemie, 2006
- Diastereoselective rhodium-catalyzed nitrene transfer starting from chiral sulfonimidamide-derived iminoiodanesTetrahedron: Asymmetry, 2005
- Sulfonimidamides: Efficient Chiral Iminoiodane Precursors for Diastereoselective Copper-Catalyzed Aziridination of OlefinsOrganic Letters, 2004