Controllable Phosphorylation of Thioesters: Selective Synthesis of Aryl and Benzyl Phosphoryl Compounds.

The controllable phosphorylations of thioesters were developed. When the reaction was catalyzed by a palladium catalyst, aryl or alkenyl phosphoryl compounds were generated through decarbonylative coupling; while the benzyl phosphoryl compounds would be produced through deoxygenative coupling when the reaction was carried out in the presence of only a base.

[1]  Yuan Wang,et al.  Palladium-catalyzed phosphorylation of benzyl ammonium triflates with P(O)H compounds , 2020 .

[2]  Junichiro Yamaguchi,et al.  Catalytic Deoxygenative Coupling of Aromatic Esters with Organophosphorus Compounds. , 2020, Journal of the American Chemical Society.

[3]  Tieqiao Chen,et al.  Palladium-Catalyzed Direct Decarbonylative Phosphorylation of Benzoic Acids with P(O)-H Compounds , 2020 .

[4]  Xin Hong,et al.  Decarbonylative Phosphorylation of Carboxylic Acids via Redox-Neutral Palladium Catalysis. , 2019, Organic letters.

[5]  G. Deng,et al.  Thioesters as Bifunctional Reagents for 2‐Naphthylamine Sulfuracylation , 2019, Advanced Synthesis & Catalysis.

[6]  S. Yin,et al.  General Oxidative Aryl C-P Bond Formation through Palladium-Catalyzed Decarbonylative Coupling of Aroylhydrazides with P(O)H Compounds. , 2019, Organic letters.

[7]  P. Gehrtz,et al.  Tandem Acyl Substitution/Michael Addition of Thioesters with Vinylmagnesium Bromide. , 2019, Organic letters.

[8]  Bo Yang,et al.  Ni-Catalyzed C-P Coupling of Aryl, Benzyl, or Allyl Ammonium Salts with P(O)H Compounds. , 2019, The Journal of organic chemistry.

[9]  P. Gehrtz,et al.  Nickel-Catalyzed Coupling of Arylzinc Halides with Thioesters. , 2018, Chemistry.

[10]  Haobin Wang,et al.  Direct Aryloxylation/Alkyloxylation of Dialkyl Phosphonates for the Synthesis of Mixed Phosphonates. , 2018, Angewandte Chemie.

[11]  P. Gehrtz,et al.  Metal-Catalyzed Synthesis and Use of Thioesters: Recent Developments. , 2018, Chemistry.

[12]  Junichiro Yamaguchi,et al.  Decarbonylative Aryl Thioether Synthesis by Ni Catalysis , 2018, Chemistry Letters.

[13]  Yue-E Liu,et al.  The Liebeskind–Srogl Cross‐Coupling Reaction and its Synthetic Applications , 2018 .

[14]  M. Murakami,et al.  Synthetic Approach to Benzocyclobutenones Using Visible Light and a Phosphonate Auxiliary. , 2018, Organic letters.

[15]  Junichiro Yamaguchi,et al.  Decarbonylative C-P Bond Formation Using Aromatic Esters and Organophosphorus Compounds. , 2018, Organic letters.

[16]  Chaonan Dong,et al.  Copper‐Catalyzed Dehydrative Cyclization of 1‐(2‐Hydroxyphenyl)propargyl Alcohols with P(O)H Compounds for the Synthesis of 2‐Phosphorylmethylbenzofurans , 2018 .

[17]  M. Sanford,et al.  Palladium- and Nickel-Catalyzed Decarbonylative C-S Coupling to Convert Thioesters to Thioethers. , 2018, Organic letters.

[18]  S. Ueno,et al.  Palladium-catalyzed Benzylic Substitution of Benzyl Carbonates with Phosphorus Nucleophiles , 2017 .

[19]  M. Szostak,et al.  Decarbonylative Phosphorylation of Amides by Palladium and Nickel Catalysis: The Hirao Cross-Coupling of Amide Derivatives. , 2017, Angewandte Chemie.

[20]  T. Hosoya,et al.  Facile Transformation of α,β-Unsaturated Carboxylic Acids to Alkenylboronic Esters via Rhodium-catalyzed Decarbonylative Borylation of α,β-Unsaturated Thioesters , 2017 .

[21]  T. Wen,et al.  K2S2O8-Promoted Direct C–H Phosphorylation of (Benzo)thiazoles , 2017 .

[22]  T. Hosoya,et al.  Rhodium‐Catalyzed Decarbonylative Borylation of Aromatic Thioesters for Facile Diversification of Aromatic Carboxylic Acids , 2017, Angewandte Chemie.

[23]  Z. Gu,et al.  Cleavage of the C(O)-S Bond of Thioesters by Palladium/Norbornene/Copper Cooperative Catalysis: An Efficient Synthesis of 2-(Arylthio)aryl Ketones. , 2016, Journal of the American Chemical Society.

[24]  Hao Wei,et al.  Practical way for the synthesis of phosphine oxides and phosphine sulfides from benzyl alcohol derivatives , 2016 .

[25]  Y. Kishi,et al.  One-Pot Ketone Synthesis with Alkylzinc Halides Prepared from Alkyl Halides via a Single Electron Transfer (SET) Process: New Extension of Fukuyama Ketone Synthesis. , 2016, Journal of the American Chemical Society.

[26]  N. Maulide,et al.  Enantioconvergent Fukuyama Cross-Coupling of Racemic Benzylic Organozinc Reagents. , 2016, Angewandte Chemie.

[27]  H. Jakubowski.  Aminoacyl‐tRNA synthetases and the evolution of coded peptide synthesis: the Thioester World , 2016, FEBS letters.

[28]  C. So,et al.  Palladium-Catalyzed Phosphorylation of Aryl Mesylates and Tosylates. , 2015, Organic letters.

[29]  Lorenzo Galluzzi,et al.  Acetyl coenzyme A: a central metabolite and second messenger. , 2015, Cell metabolism.

[30]  Ren‐Jie Song,et al.  Rhodium(III)-Catalyzed [3+2]/[5+2] Annulation of 4-Aryl 1,2,3-Triazoles with Internal Alkynes through Dual C(sp2)-H Functionalization. , 2015, Angewandte Chemie.

[31]  F. Wurm,et al.  Poly(phosphoester)s: A New Platform for Degradable Polymers. , 2015, Angewandte Chemie.

[32]  Shannon A. Bonke,et al.  Fukuyama Reduction and Integrated Thioesterification/Fukuyama Reduction of Thioesters and Acyl Chlorides Using Continuous Flow , 2014 .

[33]  Joshua R. Gaffen,et al.  Phosphoryl-rich flame-retardant ions (FRIONs): towards safer lithium-ion batteries. , 2014, Angewandte Chemie.

[34]  Yuxing Gao,et al.  Palladium-catalyzed air-based oxidative coupling of arylboronic acids with H-phosphine oxides leading to aryl phosphine oxides. , 2014, Organic & biomolecular chemistry.

[35]  J. Montchamp,et al.  Phosphinate chemistry in the 21st century: a viable alternative to the use of phosphorus trichloride in organophosphorus synthesis. , 2014, Accounts of chemical research.

[36]  Zhangjie Shi,et al.  Recent Advances in Transition-Metal-Catalyzed C–S Activation: From Thioester to (Hetero)aryl Thioether , 2014 .

[37]  Yuxing Gao,et al.  Copper-Catalyzed Synthesis of Alkylphosphonates from H-Phosphonates and N-Tosylhydrazones , 2012 .

[38]  L. Kochian.  Plant nutrition: Rooting for more phosphorus , 2012, Nature.

[39]  S. Sobhani,et al.  Nicotinium Dichromate (=3-Carboxypyridinium Dichromate; NDC) as an Efficient Reagent for the Oxidative Deamination of Amines and Aminophosphonates , 2012 .

[40]  Sunwoo Lee,et al.  One-pot synthesis of symmetrical and unsymmetrical aryl sulfides by Pd-catalyzed couplings of aryl halides and thioacetates. , 2011, The Journal of organic chemistry.

[41]  Yufen Zhao,et al.  Copper-catalyzed C-P bond construction via direct coupling of phenylboronic acids with H-phosphonate diesters. , 2011, Organic letters.

[42]  T. Skrydstrup,et al.  Enamides accessed from aminothioesters via a Pd(0)-catalyzed decarbonylative/β-hydride elimination sequence. , 2010, Organic letters.

[43]  J. Vasseur,et al.  5'-Bis-conjugation of oligonucleotides by amidative oxidation and click chemistry. , 2010, The Journal of organic chemistry.

[44]  A. Paytan,et al.  The oceanic phosphorus cycle. , 2007, Chemical reviews.

[45]  G. Pinna,et al.  Chiral P,N-ligands with pyridine-nitrogen and phosphorus donor atoms. Syntheses and applications in asymmetric catalysis: Tetrahedron report number 659 , 2003 .

[46]  J. Staunton,et al.  Polyketide biosynthesis: a millennium review. , 2001, Natural product reports.

[47]  J. Šrogl,et al.  Thiol Ester−Boronic Acid Coupling. A Mechanistically Unprecedented and General Ketone Synthesis , 2000 .

[48]  H. Nakazawa,et al.  Catalytic carbon-phosphorus bond activation by palladium complexes. Decarbonylation and metathesis reactions of .alpha.-ketophosphonates and isolation of aroyl(phosphonato)palladium complexes as intermediates , 1992 .

[49]  T. Fukuyama,et al.  Facile reduction of ethyl thiol esters to aldehydes: application to a total synthesis of (+)-neothramycin A methyl ether , 1990 .

[50]  H. Nakazawa,et al.  First example of catalytic decarbonylation and metathesis reactions of .alpha.-ketophosphonates promoted by a palladium complex , 1989 .

[51]  F. Westheimer.  Why nature chose phosphates. , 1987, Science.

[52]  T. Hirao,et al.  Palladium-catalyzed New Carbon-Phosphorus Bond Formation , 1982 .

[53]  G. Thyagarajan,et al.  Michaelis-Arbuzov rearrangement , 1981 .

[54]  F. Hartley,et al.  Coordination chemistry of thioethers, selenoethers, and telluroethers in transition-metal complexes , 1981 .

[55]  T. Hirao,et al.  Stereoselective synthesis of vinylphosphonate , 1980 .

[56]  E. Lindner,et al.  Notizen. Dimerisierung von Diphenyl(trifluoracetyl)phosphanoxid , 1979 .