On-Water Synthesis of Biaryl Sulfonyl Fluorides.

Herein, we report an efficient, ligand-free, and additive-free Suzuki-Miyaura coupling that is compatible with the aromatic sulfonyl fluoride functional group. The protocol proceeds at room temperature, on water, and offers facile access to a wide range of biaryl sulfonyl fluorides as bioorthogonal "click" reagents.

[1]  M. Reetz,et al.  Ligand-free Heck reactions using low Pd-loading. , 2004, Chemical communications.

[2]  I. Reardon,et al.  Lysyl residue 47 is near the subunit ATP-binding site of glutamine synthetase from Escherichia coli. , 1984, The Journal of biological chemistry.

[3]  Arani Chanda,et al.  Organic synthesis "on water". , 2009, Chemical reviews.

[4]  A. Narayanan,et al.  Rational targeting of active-site tyrosine residues using sulfonyl fluoride probes. , 2015, ACS chemical biology.

[5]  T. Govender,et al.  Cu(OAc)2 promoted Chan–Evans–Lam C–N cross coupling reactions on the N- and N′-nitrogen atoms of sulfonimidamides with aryl boronic acids , 2014 .

[6]  J. Taunton,et al.  Selective targeting of distinct active site nucleophiles by irreversible SRC-family kinase inhibitors. , 2012, Journal of the American Chemical Society.

[7]  R. Colman,et al.  Affinity labeling of rabbit muscle pyruvate kinase by a new fluorescent nucleotide alkylating agent 5'-[p-(fluorosulfonyl)benzoyl]-1,N6-ethenoadenosine. , 1981, Biochemistry.

[8]  B. Cravatt,et al.  Chemical proteomics with sulfonyl fluoride probes reveals selective labeling of functional tyrosines in glutathione transferases. , 2013, Chemistry & biology.

[9]  I. Wilson,et al.  Aromatic sulfonyl fluorides covalently kinetically stabilize transthyretin to prevent amyloidogenesis while affording a fluorescent conjugate. , 2013, Journal of the American Chemical Society.

[10]  M. Lively,et al.  Specificity and reactivity of human granulocyte elastase and cathepsin G, porcine pancreatic elastase, bovine chymotrypsin and trypsin toward inhibition with sulfonyl fluorides. , 1978, Biochimica et biophysica acta.

[11]  Nathanael S Gray,et al.  Developing irreversible inhibitors of the protein kinase cysteinome. , 2013, Chemistry & biology.

[12]  R. Colman Affinity labeling of purine nucleotide sites in proteins. , 1983, Annual review of biochemistry.

[13]  N. Leadbeater Fast, easy, clean chemistry by using water as a solvent and microwave heating: the Suzuki coupling as an illustration. , 2005, Chemical communications.

[14]  K. Sharpless,et al.  Palladium-catalyzed, ligand-free Suzuki reaction in water using aryl fluorosulfates. , 2015, Organic letters.

[15]  J. King,et al.  The Existence of Sulfenes , 1964 .

[16]  A. Narayanan,et al.  Understanding and applying tyrosine biochemical diversity. , 2014, Molecular bioSystems.

[17]  T. Govender,et al.  Pd-catalyzed C–N coupling of vinylbromides and sulfonimidamides: a facile synthesis of N′-vinylsulfonimidamides , 2015 .

[18]  Arwin J. Brouwer,et al.  Activity-based probes for rhomboid proteases discovered in a mass spectrometry-based assay , 2013, Proceedings of the National Academy of Sciences.

[19]  W. Steinkopf,et al.  Über Aromatische Sulfofluoride. II. Mitteilung , 1930 .

[20]  W. Allison,et al.  Three copies of the beta subunit must be modified to achieve complete inactivation of the bovine mitochondrial F1-ATPase by 5'-p-fluorosulfonylbenzoyladenosine. , 1986, The Journal of biological chemistry.

[21]  G. James,et al.  Inactivation of the protease inhibitor phenylmethylsulfonyl fluoride in buffers. , 1978, Analytical biochemistry.

[22]  Qiuquan Wang,et al.  Europium-labeled activity-based probe through click chemistry: absolute serine protease quantification using (153)Eu isotope dilution ICP/MS. , 2012, Angewandte Chemie.

[23]  P. Arvidsson,et al.  Synthesis of Vinyl‐ and Aryl–Acyl Sulfonimidamides Through Pd‐Catalyzed Carbonylation Using Mo(CO)6 as ex situ CO Source , 2015 .

[24]  A. Narayanan,et al.  Sulfonyl fluorides as privileged warheads in chemical biology , 2015, Chemical science.

[25]  A. Suzuki Cross-coupling reactions of organoboranes: an easy way to construct C-C bonds (Nobel Lecture). , 2011, Angewandte Chemie.

[26]  J. King Return of sulfenes , 1975 .

[27]  N. Laping,et al.  A Liquid Chromatography/Mass Spectrometry-Based Method for the Selection of ATP Competitive Kinase Inhibitors , 2005, Journal of biomolecular screening.

[28]  P. Arvidsson,et al.  Synthesis of novel aryl and heteroaryl acyl sulfonimidamides via Pd-catalyzed carbonylation using a nongaseous precursor. , 2013, Organic letters.

[29]  Younan Xia,et al.  Sulfur(VI) fluoride exchange (SuFEx): another good reaction for click chemistry. , 2014, Angewandte Chemie.

[30]  T. Govender,et al.  Cu(OAc)2‐Catalysed Oxidative Dual C–H/N–H Activation of Terminal Alkynes and N‐Deprotected Sulfonimidamides: An Easy Access to N‐Alkynylated Sulfonimidamides , 2015 .

[31]  M. Finn,et al.  "On water": unique reactivity of organic compounds in aqueous suspension. , 2005, Angewandte Chemie.

[32]  F. Andersson,et al.  Hydrophobically directed organic synthesis. , 2006, Angewandte Chemie.

[33]  Patrick S. Hanley,et al.  Nickel- and Palladium-Catalyzed Coupling of Aryl Fluorosulfonates with Aryl Boronic Acids Enabled by Sulfuryl Fluoride , 2015 .

[34]  Anna L. Bowman,et al.  Sulfonyl fluoride inhibitors of fatty acid amide hydrolase. , 2012, Journal of medicinal chemistry.