SuFEx-Based Polysulfonate Formation from Ethenesulfonyl Fluoride-Amine Adducts

Wang, Hua; Zhou, Feng; Ren, Gerui; Zheng, Qinheng; Chen, Hongli; Gao, Bing; Klivansky, Liana; Liu, Yi; Wu, Bin; Xu, Qingfeng; Lu, Jianmei; Sharpless, K. Barry; Wu, Peng

doi:10.1002/anie.201701160

Title: SuFEx-Based Polysulfonate Formation from Ethenesulfonyl Fluoride-Amine Adducts

Journal Article · Thu May 18 00:00:00 EDT 2017 · Angewandte Chemie (International Edition)

DOI:https://doi.org/10.1002/anie.201701160· OSTI ID:1425415

Wang, Hua ^[1]; Zhou, Feng ^[2]; Ren, Gerui ^[3]; Zheng, Qinheng ^[4]; Chen, Hongli ^[4]; Gao, Bing ^[4]; Klivansky, Liana ^[5]; Liu, Yi ^[5]; Wu, Bin ^[6]; Xu, Qingfeng ^[6]; Lu, Jianmei ^[6]; Sharpless, K. Barry ^[4]; Wu, Peng ^[7]

The Scripps Research Inst., La Jolla, CA (United States). Dept. of Chemical Physiology and Dept. of Chemistry
The Scripps Research Inst., La Jolla, CA (United States). Dept. of Chemistry; Soochow Univ., Suzhou (China). College of Chemistry, Chemical Engineering and Materials Science, Collaborative Innovation Center of Suzhou, Nano Science and Technology
The Scripps Research Inst., La Jolla, CA (United States). Dept. of Chemistry; Zhejiang Univ., Hangzhou (China). Dept. of Applied Chemistry and School of Food Science and Biotechnology
The Scripps Research Inst., La Jolla, CA (United States). Dept. of Chemistry
Lawrence Berkeley National Lab. (LBNL), Berkeley, CA (United States). The Molecular Foundry
Soochow Univ., Suzhou (China). College of Chemistry, Chemical Engineering and Materials Science, Collaborative Innovation Center of Suzhou, Nano Science and Technology
The Scripps Research Inst., La Jolla, CA (United States). Dept. of Chemical Physiology

In this article, the SuFEx-based polycondensation between bisalkylsulfonyl fluorides (AA monomers) and bisphenol bis(t-butyldimethylsilyl) ethers (BB monomers) using [Ph₃P=N-PPh₃]⁺[HF₂]^- as the catalyst is described. The AA monomers were prepared via the highly reliable Michael addition of ethenesulfonyl fluoride and amines/anilines while the BB monomers were obtained from silylation of bisphenols by t-butyldimethylsilyl chloride. With these reactions, a remarkable diversity of monomeric building blocks was achieved by exploiting readily available amines, anilines, and bisphenols as starting materials. The SuFEx-based polysulfonate formation reaction exhibited excellent efficiency and functional group tolerance, producing polysulfonates with a variety of side chain functionalities in >99 % conversion within 10 min to 1 h. When bearing an orthogonal group on the side chain, the polysulfonates can be further functionalized via click-chemistry-based post-polymerization modification.

View Accepted Manuscript (DOE)

View Accepted Manuscript (Publisher)

Cite

Export

Save

Research Organization:: Lawrence Berkeley National Laboratory (LBNL), Berkeley, CA (United States)

Sponsoring Organization:: USDOE Office of Science (SC), Basic Energy Sciences (BES); National Science Foundation (NSF); National Institutes of Health (NIH); National Natural Science Foundation of China (NNSF); National Basic Research Program of China

Grant/Contract Number:: AC02-05CH11231; CHE 1610987; R01GM113046; 21336005; 21176164; 21371128; 15KJA150008

OSTI ID:: 1425415

Alternate ID(s):: OSTI ID: 1374472

Journal Information:: Angewandte Chemie (International Edition), Vol. 56, Issue 37; ISSN 1433-7851

Publisher:: WileyCopyright Statement

Country of Publication:: United States

Language:: English

Citation Metrics:

Cited by: 105 works

Citation information provided by
Web of Science

References (64)

Sequence Control of Macromers via Iterative Sequential and Exponential Growth Amir, Faheem; Jia, Zhongfan; Monteiro, Michael J. Journal of the American Chemical Society, Vol. 138, Issue 51 https://doi.org/10.1021/jacs.6b10869	journal	December 2016
Click Chemistry: Diverse Chemical Function from a Few Good Reactions Kolb, Hartmuth C.; Finn, M. G.; Sharpless, K. Barry Angewandte Chemie International Edition, Vol. 40, Issue 11, p. 2004-2021 https://doi.org/10.1002/1521-3773(20010601)40:11<2004::AID-ANIE2004>3.0.CO;2-5	journal	June 2001
Generation of C ₂ F ₅ CHN ₂ In Situ and Its First Reaction: [3+2] Cycloaddition with Alkenes Mykhailiuk , Pavel K. Chemistry - A European Journal, Vol. 20, Issue 17 https://doi.org/10.1002/chem.201304840	journal	April 2014
Amine Cured Epoxide Networks: Formation, Structure, and Properties ^† Matějka, Libor Macromolecules, Vol. 33, Issue 10 https://doi.org/10.1021/ma991831w	journal	May 2000
SuFEx Click: New Materials from SO _x F and Silyl Ethers Yatvin, Jeremy; Brooks, Karson; Locklin, Jason Chemistry - A European Journal, Vol. 22, Issue 46 https://doi.org/10.1002/chem.201602926	journal	August 2016
A Convenient Catalyst for Aqueous and Protein Suzuki−Miyaura Cross-Coupling Chalker, Justin M.; Wood, Charlotte S. C.; Davis, Benjamin G. Journal of the American Chemical Society, Vol. 131, Issue 45 https://doi.org/10.1021/ja907150m	journal	November 2009
Sulfur(VI) Fluoride Exchange (SuFEx): Another Good Reaction for Click Chemistry Dong, Jiajia; Krasnova, Larissa; Finn, M. G. Angewandte Chemie International Edition, Vol. 53, Issue 36 https://doi.org/10.1002/anie.201309399	journal	August 2014
Highly Efficient “Click” Functionalization of Poly(3-azidopropyl methacrylate) Prepared by ATRP Sumerlin, Brent S.; Tsarevsky, Nicolay V.; Louche, Guillaume Macromolecules, Vol. 38, Issue 18 https://doi.org/10.1021/ma0511245	journal	September 2005
Post-polymerization functionalization of polyolefins Boaen, Nicole K.; Hillmyer, Marc A. Chemical Society Reviews, Vol. 34, Issue 3 https://doi.org/10.1039/b311405h	journal	January 2005
Postpolymerization Modification of Block Copolymers Romulus, Joy; Henssler, John T.; Weck, Marcus Macromolecules, Vol. 47, Issue 16 https://doi.org/10.1021/ma5009918	journal	August 2014
A Click Ligation Based on SuFEx for the Metal-Free Synthesis of Sugar and Iminosugar Clusters: A Click Ligation Based on SuFEx for the Metal-Free Synthesis of Sugar and Iminosugar Clusters Zelli, Renaud; Tommasone, Stefano; Dumy, Pascal European Journal of Organic Chemistry, Vol. 2016, Issue 30 https://doi.org/10.1002/ejoc.201600732	journal	August 2016
Research in Macromolecular Science: Challenges and Opportunities for the Next Decade Ober, C. K.; Cheng, S. Z. D.; Hammond, P. T. Macromolecules, Vol. 42, Issue 2 https://doi.org/10.1021/ma802463z	journal	January 2009
SuFEx on the Surface: A Flexible Platform for Postpolymerization Modification of Polymer Brushes Yatvin, Jeremy; Brooks, Karson; Locklin, Jason Angewandte Chemie, Vol. 127, Issue 45 https://doi.org/10.1002/ange.201506253	journal	September 2015
Ethensulfonylfluorid: der beste je entdeckte Michael-Akzeptor? Chen, Quan; Mayer, Peter; Mayr, Herbert Angewandte Chemie, Vol. 128, Issue 41 https://doi.org/10.1002/ange.201601875	journal	May 2016
Multifunctional Surface Manipulation Using Orthogonal Click Chemistry Brooks, Karson; Yatvin, Jeremy; McNitt, Christopher D. Langmuir, Vol. 32, Issue 26 https://doi.org/10.1021/acs.langmuir.6b01591	journal	June 2016
Synthesis of Aryl Alkyl and Aryl Vinyl Sulfones via Friedel-Crafts Reactions of Sulfonyl Fluorides Hyatt, John A.; White, Alan W. Synthesis, Vol. 1984, Issue 03 https://doi.org/10.1055/s-1984-30774	journal	January 1984
The Existence of Sulfenes King, J. F.; Durst, T. Journal of the American Chemical Society, Vol. 86, Issue 2 https://doi.org/10.1021/ja01056a038	journal	January 1964
Chemistry of ethenesulfonyl fluoride. Fluorosulfonylethylation of organic compounds Krutak, James J.; Burpitt, Robert D.; Moore, William H. The Journal of Organic Chemistry, Vol. 44, Issue 22 https://doi.org/10.1021/jo01336a022	journal	October 1979
An Efficient Organocatalyzed Interconversion of Silyl Ethers to Tosylates Using DBU and p -Toluenesulfonyl Fluoride Gembus, Vincent; Marsais, Francis; Levacher, Vincent Synlett, Vol. 2008, Issue 10 https://doi.org/10.1055/s-2008-1078407	journal	June 2008
A Stepwise Huisgen Cycloaddition Process: Copper(I)-Catalyzed Regioselective “Ligation” of Azides and Terminal Alkynes Rostovtsev, Vsevolod V.; Green, Luke G.; Fokin, Valery V. Angewandte Chemie International Edition, Vol. 41, Issue 14, p. 2596-2599 https://doi.org/10.1002/1521-3773(20020715)41:14<2596::AID-ANIE2596>3.0.CO;2-4	journal	July 2002
SuFEx-Based Synthesis of Polysulfates Dong, Jiajia; Sharpless, K. Barry; Kwisnek, Luke Angewandte Chemie, Vol. 126, Issue 36 https://doi.org/10.1002/ange.201403758	journal	August 2014
Self-Structured Surface Patterns on Epoxy-Based Azo Polymer Films Induced by Laser Light Irradiation Wang, Xiaolin; Yin, Jianjun; Wang, Xiaogong Macromolecules, Vol. 44, Issue 17 https://doi.org/10.1021/ma200832b	journal	September 2011
Anhydrous Tetrabutylammonium Fluoride Sun, Haoran; DiMagno, Stephen G. Journal of the American Chemical Society, Vol. 127, Issue 7 https://doi.org/10.1021/ja0440497	journal	February 2005
Electrical and optical properties of the system TiO2-xFx Subbarao, S. N.; Yun, Y. H.; Kershaw, R. Inorganic Chemistry, Vol. 18, Issue 2 https://doi.org/10.1021/ic50192a064	journal	February 1979
Polymer “Clicking” by CuAAC Reactions Meldal, Morten Macromolecular Rapid Communications, Vol. 29, Issue 12–13 https://doi.org/10.1002/marc.200800159	journal	July 2008
Palladium-Mediated Cell-Surface Labeling Spicer, Christopher D.; Triemer, Therese; Davis, Benjamin G. Journal of the American Chemical Society, Vol. 134, Issue 2 https://doi.org/10.1021/ja209352s	journal	December 2011
1,3-Dipolare Cycloaddition von Aziden und Alkinen: eine universelle Ligationsmethode in den Polymer- und Materialwissenschaften Lutz, Jean-François Angewandte Chemie, Vol. 119, Issue 7 https://doi.org/10.1002/ange.200604050	journal	February 2007
Synthesis of Functional Polymers by Post-Polymerization Modification Gauthier, Marc A.; Gibson, Matthew I.; Klok, Harm-Anton Angewandte Chemie International Edition, Vol. 48, Issue 1 https://doi.org/10.1002/anie.200801951	journal	November 2008
Enhanced Aqueous Suzuki–Miyaura Coupling Allows Site-Specific Polypeptide ¹⁸ F-Labeling Gao, Zhanghua; Gouverneur, Véronique; Davis, Benjamin G. Journal of the American Chemical Society, Vol. 135, Issue 37 https://doi.org/10.1021/ja4049114	journal	September 2013
Modular synthesis of block copolymers via cycloaddition of terminal azide and alkyne functionalized polymers Opsteen, Joost A.; van Hest, Jan C. M. Chemical Communications, Issue 1 https://doi.org/10.1039/b412930j	journal	January 2005
1,3-Dipolar Cycloadditions of Azides and Alkynes: A Universal Ligation Tool in Polymer and Materials Science Lutz, Jean-François Angewandte Chemie International Edition, Vol. 46, Issue 7 https://doi.org/10.1002/anie.200604050	journal	February 2007
Thermal and mechanical properties of some polysulfonates Work, J. L.; Herweh, J. E. Journal of Polymer Science Part A-1: Polymer Chemistry, Vol. 6, Issue 7 https://doi.org/10.1002/pol.1968.150060723	journal	July 1968
Combination of AGET ATRP and SuFEx for post-polymerization chain-end modifications Li, Shaohua; Beringer, Laura T.; Chen, Siyuan Polymer, Vol. 78 https://doi.org/10.1016/j.polymer.2015.09.055	journal	November 2015
Construction of functional aliphatic polycarbonates for biomedical applications Feng, Jun; Zhuo, Ren-Xi; Zhang, Xian-Zheng Progress in Polymer Science, Vol. 37, Issue 2 https://doi.org/10.1016/j.progpolymsci.2011.07.008	journal	February 2012
Ethenesulfonyl Fluoride: The Most Perfect Michael Acceptor Ever Found? Chen, Quan; Mayer, Peter; Mayr, Herbert Angewandte Chemie International Edition, Vol. 55, Issue 41 https://doi.org/10.1002/anie.201601875	journal	May 2016
The Convergence of Synthetic Organic and Polymer Chemistries Hawker, C. J. Science, Vol. 309, Issue 5738 https://doi.org/10.1126/science.1109778	journal	August 2005
Sulfated Ligands for the Copper(I)-Catalyzed Azide-Alkyne Cycloaddition Wang, Wei; Hong, Senglian; Tran, Andrew Chemistry - An Asian Journal, Vol. 6, Issue 10 https://doi.org/10.1002/asia.201100385	journal	September 2011
SuFEx-Based Synthesis of Polysulfates Dong, Jiajia; Sharpless, K. Barry; Kwisnek, Luke Angewandte Chemie International Edition, Vol. 53, Issue 36 https://doi.org/10.1002/anie.201403758	journal	August 2014
Iterative exponential growth of stereo- and sequence-controlled polymers Barnes, Jonathan C.; Ehrlich, Deborah J. C.; Gao, Angela X. Nature Chemistry, Vol. 7, Issue 10 https://doi.org/10.1038/nchem.2346	journal	September 2015
Marrying click chemistry with polymerization: expanding the scope of polymeric materials Golas, Patricia L.; Matyjaszewski, Krzysztof Chem. Soc. Rev., Vol. 39, Issue 4 https://doi.org/10.1039/B901978M	journal	January 2010
A Heck-Matsuda Process for the Synthesis of β-Arylethenesulfonyl Fluorides: Selectively Addressable Bis-electrophiles for SuFEx Click Chemistry Qin, Hua-Li; Zheng, Qinheng; Bare, Grant A. L. Angewandte Chemie, Vol. 128, Issue 45 https://doi.org/10.1002/ange.201608807	journal	October 2016
Standing on the shoulders of Hermann Staudinger: Post-polymerization modification from past to present Günay, Kemal Arda; Theato, Patrick; Klok, Harm-Anton Journal of Polymer Science Part A: Polymer Chemistry, Vol. 51, Issue 1 https://doi.org/10.1002/pola.26333	journal	October 2012
Combining Ring-Opening Metathesis Polymerization (ROMP) with Sharpless-Type “Click” Reactions: An Easy Method for the Preparation of Side Chain Functionalized Poly(oxynorbornenes) Binder, Wolfgang H.; Kluger, Christian Macromolecules, Vol. 37, Issue 25 https://doi.org/10.1021/ma0480087	journal	December 2004
Return of sulfenes King, James Frederick Accounts of Chemical Research, Vol. 8, Issue 1 https://doi.org/10.1021/ar50085a002	journal	January 1975
Preparation and properties of polyarylsulphonates Vizgert, R. V.; Budenkova, N. M.; Maksimenko, N. N. Polymer Science U.S.S.R., Vol. 31, Issue 7 https://doi.org/10.1016/0032-3950(89)90490-5	journal	January 1989
Schwefel(VI)-fluorid-Austausch (SuFEx): Eine weitere gute Anwendung für die Click-Chemie Dong, Jiajia; Krasnova, Larissa; Finn, M. G. Angewandte Chemie, Vol. 126, Issue 36 https://doi.org/10.1002/ange.201309399	journal	August 2014
Ethenesulfonyl Fluoride (ESF): An On-Water Procedure for the Kilogram-Scale Preparation Zheng, Qinheng; Dong, Jiajia; Sharpless, K. Barry The Journal of Organic Chemistry, Vol. 81, Issue 22 https://doi.org/10.1021/acs.joc.6b01423	journal	October 2016
A Block Copolymer for Functionalisation of Polymersome Surfaces van Dongen, Stijn F. M.; Nallani, Madhavan; Schoffelen, Sanne Macromolecular Rapid Communications, Vol. 29, Issue 4 https://doi.org/10.1002/marc.200700765	journal	February 2008
Synthese funktioneller Polymere durch polymeranaloge Reaktionen Gauthier, Marc A.; Gibson, Matthew I.; Klok, Harm-Anton Angewandte Chemie, Vol. 121, Issue 1 https://doi.org/10.1002/ange.200801951	journal	November 2008
Chelation-assisted CuAAC in star-shaped polymers enables fast self-healing at low temperatures Neumann, S.; Döhler, D.; Ströhl, D. Polymer Chemistry, Vol. 7, Issue 13 https://doi.org/10.1039/C5PY01818H	journal	January 2016
Sulfonyl Fluorides as Alternative to Sulfonyl Chlorides in Parallel Synthesis of Aliphatic Sulfonamides Bogolubsky, Andrey V.; Moroz, Yurii S.; Mykhailiuk, Pavel K. ACS Combinatorial Science, Vol. 16, Issue 4 https://doi.org/10.1021/co400164z	journal	February 2014
A Versatile and Scalable Strategy to Discrete Oligomers Lawrence, Jimmy; Lee, Sang-Ho; Abdilla, Allison Journal of the American Chemical Society, Vol. 138, Issue 19 https://doi.org/10.1021/jacs.6b03127	journal	May 2016
Cycloaddition Reactions of Ehtenesulfonic Acid Derivatives with Nitrones Vessi俊e, Roger; Chanet-Ray, Josette; Z屍oual, Abdellah HETEROCYCLES, Vol. 26, Issue 1 https://doi.org/10.3987/R-1987-01-0101	journal	January 1987
SuFEx on the Surface: A Flexible Platform for Postpolymerization Modification of Polymer Brushes Yatvin, Jeremy; Brooks, Karson; Locklin, Jason Angewandte Chemie International Edition, Vol. 54, Issue 45 https://doi.org/10.1002/anie.201506253	journal	September 2015
Visible Light Photocatalytic Thiol–Ene Reaction: An Elegant Approach for Fast Polymer Postfunctionalization and Step-Growth Polymerization Xu, Jiangtao; Boyer, Cyrille Macromolecules, Vol. 48, Issue 3 https://doi.org/10.1021/ma502460t	journal	January 2015
Analysis of bisphenol A sulfonate–carboxylate polymer Forrette, John E.; Burroughs, James E.; Booker, Christine C. Journal of Applied Polymer Science, Vol. 12, Issue 9 https://doi.org/10.1002/app.1968.070120906	journal	September 1968
Thiol–ene “click” reactions and recent applications in polymer and materials synthesis: a first update Lowe, Andrew B. Polym. Chem., Vol. 5, Issue 17 https://doi.org/10.1039/C4PY00339J	journal	January 2014
Peptidotriazoles on Solid Phase [1,2,3]-Triazoles by Regiospecific Copper(I)-Catalyzed 1,3-Dipolar Cycloadditions of Terminal Alkynes to Azides Tornøe, Christian W.; Christensen, Caspar; Meldal, Morten The Journal of Organic Chemistry, Vol. 67, Issue 9, p. 3057-3064 https://doi.org/10.1021/jo011148j	journal	May 2002
A Heck-Matsuda Process for the Synthesis of β-Arylethenesulfonyl Fluorides: Selectively Addressable Bis-electrophiles for SuFEx Click Chemistry Qin, Hua-Li; Zheng, Qinheng; Bare, Grant A. L. Angewandte Chemie International Edition, Vol. 55, Issue 45 https://doi.org/10.1002/anie.201608807	journal	October 2016
Click-Chemie: diverse chemische Funktionalität mit einer Handvoll guter Reaktionen Kolb, Hartmuth C.; Finn, M. G.; Sharpless, K. Barry Angewandte Chemie, Vol. 113, Issue 11 https://doi.org/10.1002/1521-3757(20010601)113:11<2056::AID-ANGE2056>3.0.CO;2-W	journal	June 2001
A Stepwise Huisgen Cycloaddition Process: Copper(I)-Catalyzed Regioselective “Ligation” of Azides and Terminal Alkynes Rostovtsev, Vsevolod V.; Green, Luke G.; Fokin, Valery V. Angewandte Chemie, Vol. 114, Issue 14, p. 2708-2711 https://doi.org/10.1002/1521-3757(20020715)114:14<2708::AID-ANGE2708>3.0.CO;2-0	journal	July 2002
Iterative Exponential Growth of Stereo- and Sequence-Controlled Polymers Swager, Timothy M.; Schröder, Vera Synfacts, Vol. 12, Issue 01, p. 0037-0037 https://doi.org/10.1055/s-0035-1561070	journal	December 2015
Post-Polymerization Functionalization of Polyolefins Boaen, Nicole K.; Hillmyer, Marc A. ChemInform, Vol. 36, Issue 26 https://doi.org/10.1002/chin.200526251	journal	June 2005
1,3-Dipolar Cycloadditions of Azides and Alkynes: A Universal Ligation Tool in Polymer and Materials Science Lutz, Jean-Francois ChemInform, Vol. 38, Issue 20 https://doi.org/10.1002/chin.200720229	journal	May 2007

Cited By (26)

SuFEx Chemistry of Thionyl Tetrafluoride (SOF ₄ ) with Organolithium Nucleophiles: Synthesis of Sulfonimidoyl Fluorides, Sulfoximines, Sulfonimidamides, and Sulfonimidates Gao, Bing; Li, Suhua; Wu, Peng Angewandte Chemie, Vol. 130, Issue 7 https://doi.org/10.1002/ange.201712145	journal	January 2018
A New Portal to SuFEx Click Chemistry: A Stable Fluorosulfuryl Imidazolium Salt Emerging as an “F−SO ₂ +” Donor of Unprecedented Reactivity, Selectivity, and Scope Guo, Taijie; Meng, Genyi; Zhan, Xiongjie Angewandte Chemie, Vol. 130, Issue 10 https://doi.org/10.1002/ange.201712429	journal	February 2018
Facile Synthesis of Sequence‐Regulated Synthetic Polymers Using Orthogonal SuFEx and CuAAC Click Reactions Yang, Cangjie; Flynn, James P.; Niu, Jia Angewandte Chemie, Vol. 130, Issue 49 https://doi.org/10.1002/ange.201811051	journal	October 2018
Biocompatible SuFEx Click Chemistry: Thionyl Tetrafluoride (SOF ₄ )‐Derived Connective Hubs for Bioconjugation to DNA and Proteins Liu, Feng; Wang, Hua; Li, Suhua Angewandte Chemie, Vol. 131, Issue 24 https://doi.org/10.1002/ange.201902489	journal	May 2019
Facile Synthesis of Sequence‐Regulated Synthetic Polymers Using Orthogonal SuFEx and CuAAC Click Reactions Yang, Cangjie; Flynn, James P.; Niu, Jia Angewandte Chemie International Edition, Vol. 57, Issue 49 https://doi.org/10.1002/anie.201811051	journal	December 2018
Biocompatible SuFEx Click Chemistry: Thionyl Tetrafluoride (SOF ₄ )‐Derived Connective Hubs for Bioconjugation to DNA and Proteins Liu, Feng; Wang, Hua; Li, Suhua Angewandte Chemie International Edition, Vol. 58, Issue 24 https://doi.org/10.1002/anie.201902489	journal	June 2019
Zinc-Mediated Intermolecular Reductive Radical Fluoroalkylsulfination of Unsaturated Carbon-Carbon Bonds with Fluoroalkyl Bromides and Sulfur Dioxide Liu, Yongan; Lin, Qiongzhen; Xiao, Zhiwei Chemistry - A European Journal, Vol. 25, Issue 7 https://doi.org/10.1002/chem.201805526	journal	January 2019
Sulfur (VI) Fluoride Exchange Polymerization for Large Conjugate Chromophores and Functional Main-Chain Polysulfates with Nonvolatile Memory Performance Fan, Huiru; Ji, Yujin; Xu, Qingfeng ChemPlusChem, Vol. 83, Issue 5 https://doi.org/10.1002/cplu.201800067	journal	May 2018
2-Azidoethane-1-sulfonylfluoride (ASF): A Versatile Bis -clickable Reagent for SuFEx and CuAAC Click Reactions: 2-Azidoethane-1-sulfonylfluoride (ASF): A Versatile Bis -clickable Reagent for SuFEx and CuAAC Click Reactions Zhang, Xu; Moku, Balakrishna; Leng, Jing European Journal of Organic Chemistry, Vol. 2019, Issue 8 https://doi.org/10.1002/ejoc.201801825	journal	February 2019
Construction of Di(hetero)arylmethanes Through Pd-Catalyzed Direct Dehydroxylative Cross-Coupling of Benzylic Alcohols and Aryl Boronic Acids Mediated by Sulfuryl Fluoride (SO ₂ F ₂ ): Construction of Di(hetero)arylmethanes Through Pd-Catalyzed Direct Dehydroxylative Cross-Coupling of Benzylic Alcohols and Aryl Boronic Acids Mediated Zhao, Chuang; Zha, Gao-Feng; Fang, Wan-Yin European Journal of Organic Chemistry, Vol. 2019, Issue 8 https://doi.org/10.1002/ejoc.201801888	journal	January 2019
A Transition-Metal-Free One-Pot Cascade Process for Transformation of Primary Alcohols (RCH ₂ OH) to Nitriles (RCN) Mediated by SO ₂ F ₂: A Transition-Metal-Free One-Pot Cascade Process for Transformation of Primary Alcohols (RCH ₂ OH) to Nitriles (RCN) Mediated by SO ₂ F ₂ Jiang, Ying; Sun, Bing; Fang, Wan-Yin European Journal of Organic Chemistry, Vol. 2019, Issue 20 https://doi.org/10.1002/ejoc.201900478	journal	May 2019
Converting ( E )-(Hetero)arylethanesulfonyl Fluorides to ( Z )-(Hetero)arylethanesulfonyl Fluorides Under Light Irradiation: Converting ( E )-(Hetero)arylethanesulfonyl Fluorides to ( Z )-(Hetero)arylethanesulfonyl Fluorides Under Light Irradiation Huang, Yu-Mei; Wang, Shi-Meng; Leng, Jing European Journal of Organic Chemistry, Vol. 2019, Issue 28 https://doi.org/10.1002/ejoc.201900799	journal	July 2019
SO ₂ F ₂ -Activated Efficient Beckmann Rearrangement of Ketoximes for Accessing Amides and Lactams: SO ₂ F ₂ -Activated Efficient Beckmann Rearrangement of Ketoximes for Accessing Amides and Lactams Zhang, Guofu; Zhao, Yiyong; Xuan, Lidi European Journal of Organic Chemistry, Vol. 2019, Issue 30 https://doi.org/10.1002/ejoc.201900844	journal	July 2019
Construction of α-(Hetero)aryl Ethenesulfonyl Fluorides for SuFEx Click Chemistry: Construction of α-(Hetero)aryl Ethenesulfonyl Fluorides for SuFEx Click Chemistry Leng, Jing; Alharbi, Njud S.; Qin, Hua-Li European Journal of Organic Chemistry, Vol. 2019, Issue 35 https://doi.org/10.1002/ejoc.201901106	journal	September 2019
Highly efficient polymerization via sulfur( vi )-fluoride exchange (SuFEx): novel polysulfates bearing a pyrazoline–naphthylamide conjugated moiety and their electrical memory performance Xiao, Xiong; Zhou, Feng; Jiang, Jun Polymer Chemistry, Vol. 9, Issue 8 https://doi.org/10.1039/c7py02042b	journal	January 2018
Unsymmetrical difunctionalization of cyclooctadiene under continuous flow conditions: expanding the scope of ring opening metathesis polymerization Shen, Xianwang; Gong, Honghong; Zhou, Yang Chemical Science, Vol. 9, Issue 7 https://doi.org/10.1039/c7sc04580h	journal	January 2018
The growing applications of SuFEx click chemistry Barrow, A. S.; Smedley, C. J.; Zheng, Q. Chemical Society Reviews, Vol. 48, Issue 17 https://doi.org/10.1039/c8cs00960k	journal	January 2019
Clickable coupling of carboxylic acids and amines at room temperature mediated by SO ₂ F ₂ : a significant breakthrough for the construction of amides and peptide linkages Wang, Shi-Meng; Zhao, Chuang; Zhang, Xu Organic & Biomolecular Chemistry, Vol. 17, Issue 16 https://doi.org/10.1039/c9ob00699k	journal	January 2019
A cascade process for directly converting nitriles (RCN) to cyanamides (RNHCN) via SO ₂ F ₂ -activated Tiemann rearrangement Zhang, Guofu; Zhao, Yiyong; Ding, Chengrong Organic & Biomolecular Chemistry, Vol. 17, Issue 33 https://doi.org/10.1039/c9ob01547g	journal	January 2019
AIE-active polysulfates via a sulfur( vi ) fluoride exchange (SuFEx) click reaction and investigation of their two-photon fluorescence and cyanide detection in water and in living cells Wan, Haibo; Zhou, Shiyuan; Gu, Peiyang Polymer Chemistry, Vol. 11, Issue 5 https://doi.org/10.1039/c9py01448a	journal	January 2020
Applications of sulfuryl fluoride (SO ₂ F ₂ ) in chemical transformations Lekkala, Ravindar; Lekkala, Revathi; Moku, Balakrishna Organic Chemistry Frontiers, Vol. 6, Issue 20 https://doi.org/10.1039/c9qo00747d	journal	January 2019
But-3-ene-1,3-disulfonyl difluoride (BDF): a highly selective SuFEx clickable hub for the quick assembly of sultam-containing aliphatic sulfonyl fluorides Li, Chen; Zheng, Yujie; Rakesh, K. P. Chemical Communications, Vol. 56, Issue 58 https://doi.org/10.1039/d0cc03248d	journal	January 2020
SuFEx-enabled, agnostic discovery of covalent inhibitors of human neutrophil elastase Zheng, Qinheng; Woehl, Jordan L.; Kitamura, Seiya Proceedings of the National Academy of Sciences, Vol. 116, Issue 38 https://doi.org/10.1073/pnas.1909972116	journal	September 2019
Installation of -SO 2 F groups onto primary amides Liu, Jing; Wang, Shi-Meng; Alharbi, Njud S. Beilstein Journal of Organic Chemistry, Vol. 15 https://doi.org/10.3762/bjoc.15.186	journal	January 2019
SuFEx Chemistry of Thionyl Tetrafluoride (SOF ₄ ) with Organolithium Nucleophiles: Synthesis of Sulfonimidoyl Fluorides, Sulfoximines, Sulfonimidamides, and Sulfonimidates Gao, Bing; Li, Suhua; Wu, Peng Angewandte Chemie International Edition, Vol. 57, Issue 7 https://doi.org/10.1002/anie.201712145	journal	January 2018
A New Portal to SuFEx Click Chemistry: A Stable Fluorosulfuryl Imidazolium Salt Emerging as an “F−SO ₂ +” Donor of Unprecedented Reactivity, Selectivity, and Scope Guo, Taijie; Meng, Genyi; Zhan, Xiongjie Angewandte Chemie International Edition, Vol. 57, Issue 10 https://doi.org/10.1002/anie.201712429	journal	January 2018

Similar Records

SuFEx‐Based Polysulfonate Formation from Ethenesulfonyl Fluoride–Amine Adducts

Journal Article · Thu May 18 00:00:00 EDT 2017 · Angewandte Chemie · OSTI ID:1425415

Wang, Hua; Zhou, Feng; Ren, Gerui; +10 more

SuFExable polymers with helical structures derived from thionyl tetrafluoride

Journal Article · Mon Aug 16 00:00:00 EDT 2021 · Nature Chemistry · OSTI ID:1425415

Li, Suhua; Li, Gencheng; Gao, Bing; +13 more

Chain-Growth Sulfur(VI) Fluoride Exchange Polycondensation: Molecular Weight Control and Synthesis of Degradable Polysulfates

Journal Article · Wed Nov 03 00:00:00 EDT 2021 · ACS Central Science · OSTI ID:1425415

Kim, Hyunseok; Zhao, Jiayu; Bae, Jinhye; +6 more

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
36 MATERIALS SCIENCE
bifluoride salt
click chemistry
ethenesulfonyl fluoride
polysulfonate formation
SuFEx reaction

Title: SuFEx-Based Polysulfonate Formation from Ethenesulfonyl Fluoride-Amine Adducts

Citation Formats

References (64)

Cited By (26)

Similar Records

Related Subjects