Direct Aryloxylation/Alkyloxylation of Dialkyl Phosphonates for the Synthesis of Mixed Phosphonates

Huang, Hai; Denne, Johanna; Yang, Chou-Hsun; Wang, Haobin; Kang, Jun Yong

doi:10.1002/anie.201802082

Title: Direct Aryloxylation/Alkyloxylation of Dialkyl Phosphonates for the Synthesis of Mixed Phosphonates

Journal Article · 16 April 2018 · Angewandte Chemie (International Edition)

DOI: https://doi.org/10.1002/anie.201802082 · OSTI ID:1543471

Huang, Hai ^[1]; Denne, Johanna ^[2];

^[2];

^[1]

Univ. of Nevada, Las Vegas, NV (United States). Dept. of Chemistry and Biochemistry
Univ. of Colorado, Denver, CO (United States). Dept. of Chemistry

A strategy for the direct functionalization strategy of inertial dialkyl phosphonates with hydroxy compounds to afford diverse mixed phosphonates with good yields and functional-group tolerance has been developed. Additionally, mechanistic investigations involving both NMR studies and DFT studies suggest that an unprecedented highly reactive P^V species (phosphoryl pyridin-1-ium salt), a key intermediate for this new synthetic transformation, is generated in situ from dialkyl phosphonate in the presence of Tf₂O/pyridine.

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Research Organization:: Lawrence Berkeley National Laboratory (LBNL), Berkeley, CA (United States). National Energy Research Scientific Computing Center (NERSC); Univ. of California, Oakland, CA (United States)

Sponsoring Organization:: USDOE Office of Science (SC)

Grant/Contract Number:: AC02-05CH11231

OSTI ID:: 1543471

Journal Information:: Angewandte Chemie (International Edition), Vol. 57, Issue 22; ISSN 1433-7851

Publisher:: WileyCopyright Statement

Country of Publication:: United States

Language:: English

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Cited by: 48 works

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References (67)

Copper-Catalyzed Synthesis of Mixed Alkyl Aryl Phosphonates Fañanás-Mastral, Martín; Feringa, Ben L. Journal of the American Chemical Society, Vol. 136, Issue 28 https://doi.org/10.1021/ja505281v	journal	June 2014
Metal-Free Electrophilic Phosphination/Cyclization of Alkynes Unoh, Yuto; Hirano, Koji; Miura, Masahiro Journal of the American Chemical Society, Vol. 139, Issue 17 https://doi.org/10.1021/jacs.7b02977	journal	April 2017
Hendrickson Reagent (Triphenylphosphonium Anhydride Trifluoromethane Sulfonate) McCauley, Janice Synlett, Vol. 23, Issue 20 https://doi.org/10.1055/s-0032-1317486	journal	November 2012
Reinvestigation of the 31P NMR evidence for the formation of diorganyl phosphoropyridinium intermediates Nilsson, Johan; Kraszewski, Adam; Stawinski, Jacek Journal of the Chemical Society, Perkin Transactions 2, Issue 12 https://doi.org/10.1039/b107792a	journal	November 2001
Synthesis and Characterization of New Nitrogen-Donor-Stabilized N -Silylphosphoranimine Cations Huynh, Keith; Rivard, Eric; Lough, Alan J. Inorganic Chemistry, Vol. 46, Issue 23 https://doi.org/10.1021/ic7006342	journal	November 2007
Phosphonate Biochemistry Horsman, Geoff P.; Zechel, David L. Chemical Reviews, Vol. 117, Issue 8 https://doi.org/10.1021/acs.chemrev.6b00536	journal	October 2016
Stereospecific Reduction of Phosphine Oxides to Phosphines by the Use of a Methylation Reagent and Lithium Aluminum Hydride Imamoto, Tsuneo; Kikuchi, Shin-ichi; Miura, Tomoya Organic Letters, Vol. 3, Issue 1 https://doi.org/10.1021/ol0068041	journal	January 2001
Directed Arbuzov-type reactions of 2-cyano-1,1-dimethylethyl deoxynucleoside phosphites Nielsen, John.; Caruthers, Marvin H. Journal of the American Chemical Society, Vol. 110, Issue 18 https://doi.org/10.1021/ja00226a069	journal	August 1988
Inhibition and Labeling of Enzymes and Abzymes by Phosphonate Diesters Tramontano, A.; Ivanov, B.; Gololobov, G. Applied Biochemistry and Biotechnology, Vol. 83, Issue 1-3 https://doi.org/10.1385/ABAB:83:1-3:233	journal	January 2000
Stereospecific Coupling of H -Phosphinates and Secondary Phosphine Oxides with Amines and Alcohols: A General Method for the Preparation of Optically Active Organophosphorus Acid Derivatives ^† Wang, Gang; Shen, Ruwei; Xu, Qing The Journal of Organic Chemistry, Vol. 75, Issue 11 https://doi.org/10.1021/jo100473s	journal	June 2010
Nucleophilic β-Oniovinylation: Concept, Mechanism, Scope, and Applications Weiss, Robert; Bess, Matthias; Huber, Stefan M. Journal of the American Chemical Society, Vol. 130, Issue 14 https://doi.org/10.1021/ja071316a	journal	April 2008
Synthesis and thermal reactivity of a Me 3 N-stabilized cyclic (alkyl)(amino)oxophosphonium ion Cui, Jingjing; Li, Yongxin; Ganguly, Rakesh Inorganica Chimica Acta, Vol. 460 https://doi.org/10.1016/j.ica.2016.07.046	journal	April 2017
Intramolecular Hydrogen-Bond Participation in Phosphonylammonium Salt Formation Smith, Amos B.; Ducry, Laurent; Corbett, R. Michael Organic Letters, Vol. 2, Issue 24 https://doi.org/10.1021/ol0066330	journal	November 2000
Hammond Postulate Mirroring Enables Enantiomeric Enrichment of Phosphorus Compounds via Two Thermodynamically Interconnected Sequential Stereoselective Processes Rajendran, Kamalraj V.; Nikitin, Kirill V.; Gilheany, Declan G. Journal of the American Chemical Society, Vol. 137, Issue 29 https://doi.org/10.1021/jacs.5b04415	journal	July 2015
Selective Phosphorylation on Primary Alcohols of Unprotected Polyols Ladame, Sylvain; Claustre, Samantha; Willson, Michèle Phosphorus, Sulfur, and Silicon and the Related Elements, Vol. 174, Issue 1 https://doi.org/10.1080/10426500108040232	journal	August 2001
Glyphosate: a once-in-a-century herbicide Duke, Stephen O.; Powles, Stephen B. Pest Management Science, Vol. 64, Issue 4 https://doi.org/10.1002/ps.1518	journal	January 2008
Coordination Chemistry in Water of a Free and a Lipase-Embedded Cationic NCN-Pincer Platinum Center with Neutral and Ionic Triarylphosphines Wieczorek, Birgit; Snelders, Dennis J. M.; Dijkstra, Harm P. Organometallics, Vol. 31, Issue 7 https://doi.org/10.1021/om2010832	journal	January 2012
Experimental and computational determination of Brønsted coefficients for equilibrium transfer of the O,O-dimethyl phosphorothioyl group between oxyanion nucleophiles: EXPERIMENTAL AND COMPUTATIONAL DETERMINATION OF BRØNSTED COEFFICIENTS Edwards, David R.; Maxwell, Christopher I.; Harkness, Robert W. Journal of Physical Organic Chemistry, Vol. 25, Issue 3 https://doi.org/10.1002/poc.1903	journal	July 2011
Structural and Experimental Evidence for the Enantiomeric Recognition toward a Bulky sec -Alcohol by Candida antarctica Lipase B Park, Areum; Kim, Sunmin; Park, Jeemin ACS Catalysis, Vol. 6, Issue 11 https://doi.org/10.1021/acscatal.6b02192	journal	October 2016
Immobilization of chiral enzyme inhibitors on solid supports by amide-forming coupling and olefin metathesis Reetz, Manfred T.; Rüggeberg, Carsten J.; Dröge, Melloney J. Tetrahedron, Vol. 58, Issue 42 https://doi.org/10.1016/S0040-4020(02)01052-9	journal	October 2002
Nucleoside Phosphate and Phosphonate Prodrug Clinical Candidates: Miniperspective Thornton, Peter J.; Kadri, Hachemi; Miccoli, Ageo Journal of Medicinal Chemistry, Vol. 59, Issue 23 https://doi.org/10.1021/acs.jmedchem.6b00523	journal	September 2016
Lewis Base Stabilized Oxophosphonium Ions Hendsbee, Arthur D.; Giffin, Nick A.; Zhang, Yaoting Angewandte Chemie, Vol. 124, Issue 43 https://doi.org/10.1002/ange.201206112	journal	September 2012
Kinetics and mechanism of the aminolysis of phenyl substituted phenyl chlorophosphates with anilines in acetonitrile Guha, Arun Kanti; Lee, Hai Whang; Lee, Ikchoon Journal of the Chemical Society, Perkin Transactions 2, Issue 4 https://doi.org/10.1039/a809704f	journal	January 1999
Making the Least Reactive Electrophile the First in Class: Domino Electrophilic Activation of Amides Kaiser, Daniel; Maulide, Nuno The Journal of Organic Chemistry, Vol. 81, Issue 11 https://doi.org/10.1021/acs.joc.6b00675	journal	May 2016
Chemical Transformations Induced by Triflic Anhydride Baraznenok, Ivan L.; Nenajdenko, Valentine G.; Balenkova, Elizabeth S. Tetrahedron, Vol. 56, Issue 20 https://doi.org/10.1016/S0040-4020(00)00093-4	journal	May 2000
Remarkable Potential of the α-Aminophosphonate/Phosphinate Structural Motif in Medicinal Chemistry Mucha, Artur; Kafarski, Paweł; Berlicki, Łukasz Journal of Medicinal Chemistry, Vol. 54, Issue 17 https://doi.org/10.1021/jm200587f	journal	September 2011
The Hendrickson reagent and the Mitsunobu reaction: a mechanistic study Elson, Kathryn E.; Jenkins, Ian D.; Loughlin, Wendy A. Org. Biomol. Chem., Vol. 1, Issue 16 https://doi.org/10.1039/B305375J	journal	January 2003
Organophosphonates revealed: new insights into the microbial metabolism of ancient molecules McGrath, John W.; Chin, Jason P.; Quinn, John P. Nature Reviews Microbiology, Vol. 11, Issue 6 https://doi.org/10.1038/nrmicro3011	journal	April 2013
Palladium-Catalyzed Suzuki−Miyaura Cross-Coupling Reactions Employing Dialkylbiaryl Phosphine Ligands Martin, Ruben; Buchwald, Stephen L. Accounts of Chemical Research, Vol. 41, Issue 11 https://doi.org/10.1021/ar800036s	journal	November 2008
Anchimerically Activated ProTides as Inhibitors of Cap-Dependent Translation and Inducers of Chemosensitization in Mantle Cell Lymphoma Okon, Aniekan; Han, JingJing; Dawadi, Surendra Journal of Medicinal Chemistry, Vol. 60, Issue 19 https://doi.org/10.1021/acs.jmedchem.7b00916	journal	September 2017
Chemoselective reduction of the phosphoryl bond of O-alkyl phosphinates and related compounds: an apparently impossible transformation Kenny, Niall P.; Rajendran, Kamalraj V.; Gilheany, Declan G. Chemical Communications, Vol. 51, Issue 92 https://doi.org/10.1039/C5CC06389B	journal	January 2015
Nucleophilic ortho -Propargylation of Aryl Sulfoxides: An Interrupted Pummerer/Allenyl Thio-Claisen Rearrangement Sequence Eberhart, Andrew J.; Procter, David J. Angewandte Chemie International Edition, Vol. 52, Issue 14 https://doi.org/10.1002/anie.201300223	journal	February 2013
Reaction of the Acetals with TESOTf−Base Combination; Speculation of the Intermediates and Efficient Mixed Acetal Formation Fujioka, Hiromichi; Okitsu, Takashi; Sawama, Yoshinari Journal of the American Chemical Society, Vol. 128, Issue 17 https://doi.org/10.1021/ja060328d	journal	May 2006
Synthesis of Nucleoside Phosphate and Phosphonate Prodrugs Pradere, Ugo; Garnier-Amblard, Ethel C.; Coats, Steven J. Chemical Reviews, Vol. 114, Issue 18 https://doi.org/10.1021/cr5002035	journal	August 2014
Lewis Base Stabilized Oxophosphonium Ions Hendsbee, Arthur D.; Giffin, Nick A.; Zhang, Yaoting Angewandte Chemie International Edition, Vol. 51, Issue 43 https://doi.org/10.1002/anie.201206112	journal	September 2012
Environmental chemistry of phosphonates Nowack, Bernd Water Research, Vol. 37, Issue 11 https://doi.org/10.1016/S0043-1354(03)00079-4	journal	June 2003
Vinyl triflates derived from 1,3-dicarbonyl compounds and analogs: access and applications to organic synthesis Chassaing, Stefan; Specklin, Simon; Weibel, Jean-Marc Tetrahedron, Vol. 68, Issue 36 https://doi.org/10.1016/j.tet.2012.05.107	journal	September 2012
A flexible approach to Pd-catalyzed carbonylations via aroyl dimethylaminopyridinium salts Quesnel, Jeffrey S.; Fabrikant, Alexander; Arndtsen, Bruce A. Chemical Science, Vol. 7, Issue 1 https://doi.org/10.1039/C5SC02949J	journal	January 2016
Kinetics and Mechanism of the Aminolysis of Aryl Phenyl Chlorothiophosphates with Anilines Hoque, Md. Ehtesham Ul; Dey, Shuchismita; Guha, Arun Kanti The Journal of Organic Chemistry, Vol. 72, Issue 15 https://doi.org/10.1021/jo0700934	journal	July 2007
Reaction of 2-(2,2,2-Trifluoroethylidene)-1,3-dithiane 1-Oxide with Ketones under Pummerer Conditions and Its Application to the Synthesis of 3-Trifluoromethyl-Substituted Five-Membered Heteroarenes Kobatake, Takayuki; Yoshida, Suguru; Yorimitsu, Hideki Angewandte Chemie International Edition, Vol. 49, Issue 13 https://doi.org/10.1002/anie.200906774	journal	February 2010
Peptide-Nanoparticle Ligation Mediated by Cutinase Fusion for the Development of Cancer Cell-Targeted Nanoconjugates Galbiati, Elisabetta; Cassani, Marco; Verderio, Paolo Bioconjugate Chemistry, Vol. 26, Issue 4 https://doi.org/10.1021/acs.bioconjchem.5b00005	journal	March 2015
Anhydrides of phosphorus and sulfur acids, 2. Mixed anhydrides of phosphoric, phosphonic, and phosphinic acids with sulfonic acids and sulfuric Monoimidazolide. New methods of synthesis, novel structures, phosphorylating properties Dabkowski, Wojciech; Michalski, Jan; Skrzypczynski, Zbigniew Chemische Berichte, Vol. 118, Issue 5 https://doi.org/10.1002/cber.19851180508	journal	May 1985
Mixed alkyl aryl phosphonate esters as quenched fluorescent activity-based probes for serine proteases Serim, Sevnur; Baer, Philipp; Verhelst, Steven H. L. Organic & Biomolecular Chemistry, Vol. 13, Issue 8 https://doi.org/10.1039/C4OB02444C	journal	January 2015
Resolution of Chiral Phosphate, Phosphonate, and Phosphinate Esters by an Enantioselective Enzyme Library Nowlan, Charity; Li, Yingchun; Hermann, Johannes C. Journal of the American Chemical Society, Vol. 128, Issue 49 https://doi.org/10.1021/ja0658618	journal	December 2006
Room-Temperature meta -Functionalization: Pd(II)-Catalyzed Synthesis of 1,3,5-Trialkenyl Arene and meta -Hydroxylated Olefin Bera, Milan; Sahoo, Santosh K.; Maiti, Debabrata ACS Catalysis, Vol. 6, Issue 6 https://doi.org/10.1021/acscatal.6b00675	journal	May 2016
Direct Aerobic Oxidative Esterification and Arylation of P(O)–OH Compounds with Alcohols and Diaryliodonium Triflates Xiong, Biquan; Feng, Xiaofeng; Zhu, Longzhi ACS Catalysis, Vol. 5, Issue 2 https://doi.org/10.1021/cs501523g	journal	December 2014
Nucleophilic ortho -Propargylation of Aryl Sulfoxides: An Interrupted Pummerer/Allenyl Thio-Claisen Rearrangement Sequence Eberhart, Andrew J.; Procter, David J. Angewandte Chemie, Vol. 125, Issue 14 https://doi.org/10.1002/ange.201300223	journal	February 2013
Metal-free electrophilic phosphination of electron-rich arenes, arenols and aromatic thiols with diarylphosphine oxides Yuan, Tao; Huang, Shenlin; Cai, Chun Organic & Biomolecular Chemistry, Vol. 16, Issue 1 https://doi.org/10.1039/C7OB02620J	journal	January 2018
Remote meta -C-H Cyanation of Arenes Enabled by a Pyrimidine-Based Auxiliary Bag, Sukdev; Jayarajan, Ramasamy; Dutta, Uttam Angewandte Chemie, Vol. 129, Issue 41 https://doi.org/10.1002/ange.201706360	journal	September 2017
Microwave-Assisted Palladium-Catalyzed Cross-Coupling of Aryl and Vinyl Halides with H-Phosphonate Diesters Kalek, Marcin; Ziadi, Asraa; Stawinski, Jacek Organic Letters, Vol. 10, Issue 20 https://doi.org/10.1021/ol801935r	journal	October 2008
Phosphonate-based irreversible inhibitors of human γ-glutamyl transpeptidase (GGT). GGsTop is a non-toxic and highly selective inhibitor with critical electrostatic interaction with an active-site residue Lys562 for enhanced inhibitory activity Kamiyama, Akane; Nakajima, Mado; Han, Liyou Bioorganic & Medicinal Chemistry, Vol. 24, Issue 21 https://doi.org/10.1016/j.bmc.2016.08.050	journal	November 2016
Glutathione-analogous peptidyl phosphorus esters as mechanism-based inhibitors of γ-glutamyl transpeptidase for probing cysteinyl-glycine binding site Nakajima, Mado; Watanabe, Bunta; Han, Liyou Bioorganic & Medicinal Chemistry, Vol. 22, Issue 3 https://doi.org/10.1016/j.bmc.2013.12.034	journal	February 2014
Triphenyl phosphine ditriflate: A general oxygen activator Hendrickson, James B.; Schwartzman, Steven M. Tetrahedron Letters, Vol. 16, Issue 4 https://doi.org/10.1016/S0040-4039(00)71842-9	journal	January 1975
Mixed Aryl Phosphonate Prodrugs of a Butyrophilin Ligand Foust, Benjamin J.; Poe, Michael M.; Lentini, Nicholas A. ACS Medicinal Chemistry Letters, Vol. 8, Issue 9 https://doi.org/10.1021/acsmedchemlett.7b00245	journal	August 2017
The Effect of Structure on the Reactivity of Alkylphosphonate Esters ^1,2 Fukuto, T. R.; Metcalf, R. L. Journal of the American Chemical Society, Vol. 81, Issue 2 https://doi.org/10.1021/ja01511a025	journal	January 1959
Redox-Neutral α-Arylation of Alkyl Nitriles with Aryl Sulfoxides: A Rapid Electrophilic Rearrangement Shang, Li; Chang, Yonghui; Luo, Fan Journal of the American Chemical Society, Vol. 139, Issue 11 https://doi.org/10.1021/jacs.7b00969	journal	March 2017
A convenient method for phosphorylation using triallyl phosphite Li, Si-Zhe; Ahmar, Mohammed; Queneau, Yves Tetrahedron Letters, Vol. 56, Issue 32 https://doi.org/10.1016/j.tetlet.2015.06.030	journal	August 2015
Copper-catalyzed direct esterification of P(O)–OH compounds with phenols Xiong, Biquan; Zeng, Kui; Zhang, Shanshan Tetrahedron, Vol. 71, Issue 49 https://doi.org/10.1016/j.tet.2015.10.028	journal	December 2015
Analogues with Fluorescent Leaving Groups for Screening and Selection of Enzymes That Efficiently Hydrolyze Organophosphorus Nerve Agents Briseño-Roa, Luis; Hill, Jim; Notman, Stuart Journal of Medicinal Chemistry, Vol. 49, Issue 1 https://doi.org/10.1021/jm050518j	journal	January 2006
129. Studies on phosphorylation. Part III. Further observations on the reaction of phosphites with polyhalogen compounds in presence of bases and its application to the phosphorylation of alcohols Atherton, F. R.; Todd, A. R. Journal of the Chemical Society (Resumed) https://doi.org/10.1039/jr9470000674	journal	January 1947
Reaction of 2-(2,2,2-Trifluoroethylidene)-1,3-dithiane 1-Oxide with Ketones under Pummerer Conditions and Its Application to the Synthesis of 3-Trifluoromethyl-Substituted Five-Membered Heteroarenes Kobatake, Takayuki; Yoshida, Suguru; Yorimitsu, Hideki Angewandte Chemie, Vol. 122, Issue 13 https://doi.org/10.1002/ange.200906774	journal	February 2010
A Novel Genetic Selection System for Improved Enantioselectivity ofBacillus subtilis Lipase A Boersma, Ykelien L.; Dröge, Melloney J.; van der Sloot, Almer M. ChemBioChem, Vol. 9, Issue 7 https://doi.org/10.1002/cbic.200700754	journal	May 2008
Nucleophilic substitution at phosphorus: stereochemistry and mechanisms Kolodiazhnyi, Oleg I.; Kolodiazhna, Anastasy Tetrahedron: Asymmetry, Vol. 28, Issue 12 https://doi.org/10.1016/j.tetasy.2017.10.022	journal	December 2017
Insights into a surprising reaction: The microwave-assisted direct esterification of phosphinic acids Keglevich, György; Kiss, Nóra Zsuzsa; Mucsi, Zoltán Organic & Biomolecular Chemistry, Vol. 10, Issue 10 https://doi.org/10.1039/c2ob06972e	journal	January 2012
Remote meta -C-H Cyanation of Arenes Enabled by a Pyrimidine-Based Auxiliary Bag, Sukdev; Jayarajan, Ramasamy; Dutta, Uttam Angewandte Chemie International Edition, Vol. 56, Issue 41 https://doi.org/10.1002/anie.201706360	journal	September 2017
The H-phosphonate approach to oligonucleotide synthesis. An investigation on the mechanism of the coupling step Sigurdsson, Susannah; Strömberg, Roger J. Chem. Soc., Perkin Trans. 2, Issue 10 https://doi.org/10.1039/b205142g	journal	January 2002
Reaction of the Acetals with TESOTf—Base Combination — Speculation of the Intermediates and Efficient Mixed Acetal Formation. Fujioka, Hiromichi; Okitsu, Takashi; Sawama, Yoshinari ChemInform, Vol. 37, Issue 38 https://doi.org/10.1002/chin.200638057	journal	September 2006

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