Literature DB >> 32459499

SuFEx Activation with Ca(NTf2)2: A Unified Strategy to Access Sulfamides, Sulfamates, and Sulfonamides from S(VI) Fluorides.

Subham Mahapatra1, Cristian P Woroch2, Todd W Butler1, Sabrina N Carneiro2, Sabrina C Kwan2, Samuel R Khasnavis2, Junha Gu2, Jason K Dutra1, Beth C Vetelino1, Justin Bellenger1, Christopher W Am Ende1, Nicholas D Ball2.   

Abstract

A method to activate sulfamoyl fluorides, fluorosulfates, and sulfonyl fluorides with calcium triflimide and DABCO for SuFEx with amines is described. The reaction was applied to a diverse set of sulfamides, sulfamates, and sulfonamides at room temperature under mild conditions. Additionally, we highlight this transformation to parallel medicinal chemistry to generate a broad array of nitrogen-based S(VI) compounds.

Entities:  

Year:  2020        PMID： 32459499     DOI： 10.1021/acs.orglett.0c01397

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  13 in total

1.  Accelerated SuFEx Click Chemistry For Modular Synthesis.

Authors:  Christopher J Smedley; Joshua A Homer; Timothy L Gialelis; Andrew S Barrow; Rebecca A Koelln; John E Moses
Journal:  Angew Chem Int Ed Engl       Date:  2021-12-07       Impact factor: 15.336

2.  Diversity oriented clicking delivers β-substituted alkenyl sulfonyl fluorides as covalent human neutrophil elastase inhibitors.

Authors:  Yunfei Cheng; Gencheng Li; Christopher J Smedley; Marie-Claire Giel; Seiya Kitamura; Jordan L Woehl; Giulia Bianco; Stefano Forli; Joshua A Homer; John R Cappiello; Dennis W Wolan; John E Moses; K Barry Sharpless
Journal:  Proc Natl Acad Sci U S A       Date:  2022-09-07       Impact factor: 12.779

3.  Modular Two-Step Route to Sulfondiimidamides.

Authors:  Ze-Xin Zhang; Charles Bell; Mingyan Ding; Michael C Willis
Journal:  J Am Chem Soc       Date:  2022-06-21       Impact factor: 16.383

4.  Calcium Bistriflimide-Mediated Sulfur(VI)-Fluoride Exchange (SuFEx): Mechanistic Insights toward Instigating Catalysis.

Authors:  Brian Han; Samuel R Khasnavis; Matthew Nwerem; Michael Bertagna; Nicholas D Ball; O Maduka Ogba
Journal:  Inorg Chem       Date:  2022-06-14       Impact factor: 5.436

5.  SuFExable NH-Pyrazoles via 1,3-Dipolar Cycloadditions of Diazo Compounds with Bromoethenylsulfonyl Fluoride.

Authors:  Pavel Yamanushkin; Kemal Kaya; Mark Aldren M Feliciano; Brian Gold
Journal:  J Org Chem       Date:  2022-02-10       Impact factor: 4.198

6.  Development of BRD4 inhibitors as anti-inflammatory agents and antidotes for arsenicals.

Authors:  Marina Fosso Yatchang; Bini Mathew; Ritesh K Srivastava; Jasim Khan; Suhail Muzaffar; Sixue Zhang; Mousheng Wu; Ling Zhai; Pedro Ruiz; Anupam Agarwal; James R Bostwick; Mark J Suto; Mohammad Athar; Corinne E Augelli-Szafran
Journal:  Bioorg Med Chem Lett       Date:  2022-03-19       Impact factor: 2.940

7.  Complementary Base Lowers the Barrier in SuFEx Click Chemistry for Primary Amine Nucleophiles.

Authors:  Jan-Niclas Luy; Ralf Tonner
Journal:  ACS Omega       Date:  2020-11-23

8.  Introducing SuFNucs: Sulfamoyl-Fluoride-Functionalized Nucleosides That Undergo Sulfur Fluoride Exchange Reaction.

Authors:  Mikołaj Chrominski; Kamil Ziemkiewicz; Joanna Kowalska; Jacek Jemielity
Journal:  Org Lett       Date:  2022-06-30       Impact factor: 6.072

9.  Synthesis of unsymmetrical sulfamides and polysulfamides via SuFEx click chemistry.

Authors:  Ryan W Kulow; Jiun Wei Wu; Cheoljae Kim; Quentin Michaudel
Journal:  Chem Sci       Date:  2020-07-13       Impact factor: 9.825

10.  Modular Synthesis of Alkenyl Sulfamates and β-Ketosulfonamides via Sulfur(VI) Fluoride Exchange (SuFEx) Click Chemistry and Photomediated 1,3-Rearrangement.

Authors:  Felipe Cesar Sousa E Silva; Katarzyna Doktor; Quentin Michaudel
Journal:  Org Lett       Date:  2021-06-20       Impact factor: 6.072
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