Advances in radical phosphorylation from 2016 to 2021

Abstract

Organophosphorus compounds are of great significance in organic chemistry. Therefore, the construction of phosphorus-containing compounds has attracted significant attention from organic chemists. Radical phosphorylation has become a powerful strategy for building organophosphorus compounds and numerous achievements have been realized in recent years. In this review, we summarize the development of the generation and application of phosphorus radicals in organic chemistry since 2016. Special emphasis is given to various new transformations involving the generation of P-centered radicals via transition metal catalytic, photochemical and electrochemical means. Recent advances in the development of metal-free catalytic phosphorylations involving P-centered radicals are also reviewed.

Keywords

Organophosphorus compounds / phosphorus radicals / transition metal catalysis / visible-light photoredox catalysis / unsaturated compounds

References

[1] Tang W.New chiral phosphorus ligands for enantioselective hydrogenation.Chem Rev2003;103:3029-70

[2] Demmer CS,Bunch L.Review on modern advances of chemical methods for the introduction of a phosphonic acid group.Chem Rev2011;111:7981-8006

[3] Duffy MP,Bouit PA.π-Conjugated phospholes and their incorporation into devices: components with a great deal of potential.Chem Soc Rev2016;45:5296-310

[4] der Jeught S, Stevens CV. Direct phosphonylation of aromatic azaheterocycles.Chem Rev2009;109:2672-702

[5] Shao C,Li L.Recent advances of transition metal-catalyzed P-C coupling reactions.Chin J Org Chem2017;37:335

[6] Gao Y,Zhao Y.Recent progress toward organophosphorus compounds based on phosphorus-centered radical difunctionalizations.Phosphorus, Sulfur, and Silicon and the Related Elements2017;192:589-96

[7] Lan X,Xing Y.Recent Advances in Radical Difunctionalization of Simple Alkenes: Recent Advances in Radical Difunctionalization of Simple Alkenes.Eur J Org Chem2017;2017:5821-51

[8] Gao Y,Zhao Y.Recent advances of phosphorus-centered radical promoted difunctionalization of unsaturated carbon-carbon bonds.Chin J Org Chem2018;38:62

[9] Cai B,Xiao W.Visible light-mediated C P bond formation reactions.Science Bulletin2019;64:337-50

[10] Chen L,Zou Y.Recent advances in the construction of phosphorus-substituted heterocycles, 2009-2019.Adv Synth Catal2020;362:1724-818

[11] Ung SP,Li C.Shining light on the light-bearing element: a brief review of photomediated C-H phosphorylation reactions.Synthesis2021;53:1003-22

[12] Leca D,Lacôte E.Recent advances in the use of phosphorus-centered radicals in organic chemistry.Chem Soc Rev2005;34:858-65

[13] Rueping M,Koenigs RM.Photoredox catalyzed C-P bond forming reactions-visible light mediated oxidative phosphonylations of amines.Chem Commun (Camb)2011;47:8679-81

[14] Kingston C,Takahira Y.A survival guide for the "Electro-curious".Acc Chem Res2020;53:72-83 PMCID:PMC6996934

[15] Budnikova YH,Grinenko VV,Khrizanforov MN.Eco-efficient electrocatalytic C-P bond formation.Pure and Applied Chemistry2017;89:311-30

[16] Bezzenine-Lafollée S,Prim D.First-row late transition metals for catalytic alkene hydrofunctionalisation: recent advances in C-N, C-O and C-P bond formation.Molecules2017;22:1901 PMCID:PMC6150243

[17] Yoo W.Hydrophosphinylation of unactivated alkenes with secondary phosphine oxides under visible-light photocatalysis.Green Chem2013;15:1844

[18] Wang N,Li Z.Hydrofunctionalization of alkenols triggered by the addition of diverse radicals to unactivated alkenes and subsequent remote hydrogen atom translocation.Org Chem Front2018;5:2810-4

[19] Yuan Z,Li M.Visible light induced hydrophosphinylation of unactivated alkenes catalyzed by salicylaldehyde.Green Chem2021;23:3600-6

[20] Li YM,Wang HL,Yang SD.Direct annulations toward phosphorylated oxindoles: silver-catalyzed carbon-phosphorus functionalization of alkenes.Angew Chem Int Ed Engl2013;52:3972-6

[21] Li Y,Chang K.Metal-free oxidative arylphosphination of activated N-substituted-N-arylacrylamide derivatives using K2S2O8.Tetrahedron2014;70:1991-6

[22] Zhao J,Li X,Li F.Straightforward synthesis of functionalized chroman-4-ones through cascade radical cyclization-coupling of 2-(allyloxy)arylaldehydes.Chem Commun (Camb)2016;52:3661-4

[23] Liu Q,Xie G.Metal-free synthesis of phosphinoylchroman-4-ones via a radical phosphinoylation-cyclization cascade mediated by K₂S₂O₈.Beilstein J Org Chem2020;16:1974-82 PMCID:PMC7431760

[24] Zhang HY,Yang B.Copper-catalyzed radical cascade cyclization for the synthesis of phosphorated indolines.Chem Commun (Camb)2015;51:4101-4

[25] Liang D,Lv Y,Wang B.Silver-catalyzed radical arylphosphorylation of unactivated alkenes: synthesis of 3-phosphonoalkyl indolines.J Org Chem2018;83:4681-91

[26] Liu X,Lv Q.Silver-mediated radical phosphorylation/cyclization of N -allylbenzamides to access phosphoryl-substituted dihydroisoquinolones.New J Chem2019;43:12221-4

[27] Liu X,Chen X.Visible-light-promoted transition-metal-free approach toward phosphoryl-substituted dihydroisoquinolones via cascade phosphorylation/cyclization of N-allylbenzamides.Adv Synth Catal2019;361:3712-7

[28] Liu J,Song W.Silver-catalyzed carbon-phosphorus functionalization for polyheterocycle formation.Adv Synth Catal2017;359:609-15

[29] Gorre R,Balasubramanian S.Visible-light-driven metal-free aerobic synthesis of highly diastereoselective phosphinoylpyrroloindoles.Org Biomol Chem2020;18:1354-8

[30] Li Y,Yang S.Visible-light-induced tandem phosphorylation cyclization of vinyl azides under mild conditions.Org Chem Front2018;5:822-6

[31] Sun K,Chen X.Synthesis of phosphoryl-substituted benzimidazo[2,1-a]isoquinolin-6(5 H)-ones from 2-arylbenzoimidazoles and diarylphosphine oxides.Asian J Org Chem2019;8:2042-5

[32] Jiang SS,Wu YC,Song RJ.Manganese(III)-promoted tandem phosphinoylation/cyclization of 2-arylindoles/2-arylbenzimidazoles with disubstituted phosphine oxides.Org Biomol Chem2020;18:4843-7

[33] Fu Q,Ye JH.Transition metal-free phosphonocarboxylation of alkenes with carbon dioxide via visible-light photoredox catalysis.Nat Commun2019;10:3592 PMCID:PMC6689110

[34] Jiang Y,Fu Q,Yu D.Visible-light-driven phosphonoalkylation of alkenes.Synlett2021;32:378-82

[35] Chu XQ,Meng H,Ji SJ.Radical phosphinylation of α,α-diaryl allylic alcohols with concomitant 1,2-aryl migration.Chem Commun (Camb)2014;50:7642-5

[36] Mi X,Huang M,Wu Y.Silver-catalyzed carbonphosphonation of α,α-diaryl allylic alcohols: synthesis of β-aryl-γ-ketophosphonates.Org Biomol Chem2014;12:8394-7

[37] Yin Y,Sun JG.Eosin Y-catalyzed, visible-light-promoted carbophosphinylation of allylic alcohols via a radical neophyl rearrangement.Org Biomol Chem2018;16:2356-61

[38] Li C,Yang Q,Yang S.Visible-light-catalyzed phosphonation-annulation: an efficient strategy to synthesize β-Phosphonopyrrolidines and β-phosphonolactones: visible-light-catalyzed phosphonation-annulation: an efficient strategy to synthesize β-phosphonopyrrolidines and β-phosphonolactones^†.Chin J Chem2018;36:1052-8

[39] Wang C,Liu X,Zhao B.Photo-induced phosphorus radical involved semipinacol rearrangement reaction: highly synthesis of γ-oxo-phosphonates.Chinese Chemical Letters2020;31:677-80

[40] Jin S,Yu JT.The silver-promoted phosphonation/alkynylation of alkene proceeding with radical 1,2-alkynyl migration.J Org Chem2019;84:11177-85

[41] Zhang PZ,Li JA,Zou JP.Phosphinoyl radical initiated vicinal cyanophosphinoylation of alkenes.Org Lett2017;19:5537-40

[42] Zhang G,Chen P,Liu G.Proton-coupled electron transfer enables tandem radical relay for asymmetric copper-catalyzed phosphinoylcyanation of styrenes.Org Lett2019;21:5015-20

[43] He Y,Kim J.One-pot bifunctionalization of unactivated alkenes, P(O)-H compounds, and N-methoxypyridinium salts for the construction of β-pyridyl alkylphosphonates.Org Chem Front2018;5:2595-603

[44] Buquoi JQ,Gu X.Heteroarene phosphinylalkylation via a catalytic, polarity-reversing radical cascade.ACS Catal2019;9:5330-5 PMCID:PMC6608589

[45] Lear JM,Gu X,Mustafa DN.Multi-component heteroarene couplings via polarity-reversed radical cascades.Chem Commun (Camb)2019;55:8820-3 PMCID:PMC6650346

[46] Shen J,Yu Y.Metal-free visible-light-induced photoredox-catalyzed intermolecular pyridylation/phosphinoylation of alkenes.Org Chem Front2021;8:901-7

[47] Maryanoff BE.The Wittig olefination reaction and modifications involving phosphoryl-stabilized carbanions. Stereochemistry, mechanism, and selected synthetic aspects.Chem Rev1989;89:863-927

[48] Wei W.Catalytic and direct oxyphosphorylation of alkenes with dioxygen and H-phosphonates leading to β-ketophosphonates.Angew Chem Int Ed Engl2011;50:9097-9

[49] Zhou M,Song Q.Cu/Fe-cocatalyzed formation of β-Ketophosphonates by a domino knoevenagel-decarboxylation-oxyphosphorylation sequence from aromatic aldehydes and H-phosphonates.Chemistry2015;21:10654-9

[50] Chen X,Li X.Acetonitrile-dependent oxyphosphorylation: a mild one-pot synthesis of β-ketophosphonates from alkenyl acids or alkenes.Tetrahedron2017;73:2439-46 PMCID:PMC5475365

[51] Fu Q,Zhang Z.Copper-catalyzed aerobic oxidative coupling of ketones with P(O)-H compounds leading to β-ketophosphine oxides.Org Chem Front2017;4:1385-9

[52] Zhang Z,Fu Q.Copper catalyzed one-pot synthesis of β-ketophosphine oxides from ketones and H-phosphine oxides.Tetrahedron Letters2017;58:2417-20

[53] Liang W,Yi D.Copper-catalyzed direct oxyphosphorylation of enamides with P(O)-H compounds and dioxygen.Chin J Chem2017;35:1378-82

[54] Nan G.Direct synthesis of β-ketophosphine oxides via copper-catalyzed difunctionalization of alkenes with H-phosphine oxides and dioxygen.Tetrahedron Letters2018;59:2071-4

[55] Wang H,Zhang Z,Ji J.Hydrochloric acid-promoted copper/iron-cocatalyzed deesterifica-tive oxyphosphorylation of 2-substituted acrylates with H-phosphine oxides.Chin J Org Chem2018;38:1977

[56] Feng S,He F.A copper-catalyzed radical coupling/fragmentation reaction: efficient access to β-oxophosphine oxides.Org Chem Front2019;6:946-51

[57] Gu J.Cu(I)/Fe(III)-Catalyzed C-P cross-coupling of styrenes with H-phosphine oxides: a facile and selective synthesis of alkenylphosphine oxides and β-ketophosphonates.Org Biomol Chem2017;15:4226-30

[58] Moghaddam FM,Azaryan R.Copper ferrite nanoparticles catalyzed formation of β-Ketophosphonates via oxyphosphorylation of styrenes with H-phosphonates: a DFT study on UV-vis absorption spectra.Catalysis Communications2020;141:106015

[59] Shi Y,Guo K.Visible light-promoted metal-free aerobic oxyphosphorylation of olefins: a facile approach to β-ketophosphine oxides.Tetrahedron Letters2018;59:2062-5

[60] Qian HF,Zhou ZH,Shoberu A.Visible light-mediated photocatalytic metal-free cross-coupling reaction of alkenyl carboxylic acids with diarylphosphine oxides leading to β-ketophosphine oxides.Org Lett2018;20:5947-51

[61] Jung HI.Visible light-mediated photocatalytic phosphorylation of vinyl azides: A mild synthesis of β-ketophosphine oxides.Synthetic Communications2020;50:380-7

[62] Li M,Hu D.Catalyst-free direct difunctionalization of alkenes with H-phosphine oxides and dioxygen: a facile and green approach to β-hydroxyphosphine oxides.Tetrahedron Letters2016;57:2642-6

[63] Peng P,Peng L,Wang G.Dioxygen-induced oxidative activation of a P-H bond: radical oxyphosphorylation of alkenes and alkynes toward β-oxy phosphonates.Chem Commun (Camb)2016;52:12338-41

[64] Yi D,Chen S.Copper-catalyzed direct hydroxyphosphorylation of electron-deficient alkenes with H-phosphine oxides and dioxygen.Tetrahedron Letters2017;58:2058-61

[65] Chen Y,Lu S.Copper-catalyzed three-component phosphorylation-peroxidation of alkenes.Org Chem Front2018;5:972-6

[66] Shen J,Hou Y.Cobalt(II)-catalyzed bisfunctionalization of alkenes with diarylphosphine oxide and peroxide.Adv Synth Catal2019;361:5198-209

[67] Zhou SF,Liu K,Asekun OT.Direct radical acetoxyphosphorylation of styrenes mediated by manganese(III).J Org Chem2015;80:1214-20

[68] Ryzhakov D,Baltaze JP,Kouklovsky C.Synthesis of 3,3-spirocyclic 2-phosphonoindolines via a dearomative addition of phosphonyl radicals to indoles.Org Lett2019;21:4986-90

[69] Yang B,Ding S.Cerium(IV)-promoted phosphinoylation-nitratation of alkenes.Adv Synth Catal2018;360:4470-4

[70] Zhang C,Zhu L,Wang Z.Silver-catalyzed radical phosphonofluorination of unactivated alkenes.J Am Chem Soc2013;135:14082-5

[71] Li JA,Liu K,Zou JP.Phosphinoyl radical-initiated α,β-aminophosphinoylation of alkenes.Org Lett2017;19:4704-6

[72] Wang Y,Tang R,Tao W.Iron(III)-catalyzed radical α,β-aminophosphinoylation of styrenes with diphenylphosphine oxides and anilines.Org Biomol Chem2018;16:7782-6

[73] Xu J,Gao Y.Mn(III)-mediated phosphonation-azidation of alkenes: a facile synthesis of β-azidophosphonates.Chem Commun (Camb)2015;51:11240-3

[74] Ma X,Ge L.Iron phthalocyanine-catalyzed radical phosphinoylazidation of alkenes: a facile synthesis of β-azido-phosphine oxide with a fast azido transfer step.Chinese Journal of Catalysis2021;42:1634-40

[75] Tao ZK,Zhang PZ,Zou JP.Phosphinoyl radical-Initiated 1,2-bifunctional thiocyanodiphenylphosphinoylation of alkenes.J Org Chem2018;83:2418-24

[76] Huang T,Guo H,Ogawa A.Radical hydrophosphorylation of alkynes with R₂P(O)H generating alkenylphosphine oxides: scope and limitations.J Org Chem2018;83:8743-9

[77] Wang H,Tang Z.Z-Selective addition of diaryl phosphine oxides to alkynes via photoredox catalysis.ACS Catal2018;8:10599-605

[78] Liu WQ,Zhou S.Cobaloxime catalysis: selective synthesis of alkenylphosphine oxides under visible light.J Am Chem Soc2019;141:13941-7

[79] Hou H,Wang J.Stereo- and Regioselective cis-hydrophosphorylation of 1,3-enynes enabled by the visible-light irradiation of NiCl₂(PPh₃)₂.Org Lett2021;23:2981-7

[80] Zhang P,Gao Y.Copper-catalyzed tandem phosphination-decarboxylation-oxidation of alkynyl acids with H-phosphine oxides: a facile synthesis of β-ketophosphine oxides.Chem Commun (Camb)2015;51:7839-42

[81] Chen X,Chen XL.A one-pot strategy to synthesize β-ketophosphonates: silver/copper catalyzed direct oxyphosphorylation of alkynes with H-phosphonates and oxygen in the air.Chem Commun (Camb)2015;51:3846-9

[82] Yi N,Zou H,Fu W.Copper/Iron-catalyzed aerobic oxyphosphorylation of terminal alkynes leading to β-ketophosphonates.J Org Chem2015;80:5023-9

[83] Zhou M,Zhou Y.β-ketophosphonate formation via aerobic oxyphosphorylation of alkynes or alkynyl carboxylic acids with H-phosphonates.Org Lett2015;17:1786-9

[84] Zhong W,Shi L.Base-promoted direct oxyphosphorylation of alkynes with h-phosphine oxides in the presence of water.Synlett2018;29:1379-84

[85] Tao ZK,Li JA,Zhang W.Copper-catalyzed vicinal cyano-, thiocyano-, and chlorophosphorylation of alkynes: a phosphinoyl radical-initiated approach for difunctionalized alkenes.Org Lett2021;23:4342-7

[86] Zhang P,Zhang L.Copper-Catalyzed Cycloaddition between secondary phosphine oxides and alkynes: synthesis of benzophosphole oxides.Adv Synth Catal2016;358:138-42

[87] Quint V,Lohier JF,Gaumont AC.Metal-Free, Visible light-photocatalyzed synthesis of benzo[B]phosphole oxides: synthetic and mechanistic investigations.J Am Chem Soc2016;138:7436-41

[88] Zhu XT,Liu F.Silver-mediated radical 5-exo-dig cyclization of 2-alkynylbenzonitriles: synthesis of phosphinylated 1-indenones.Chem Commun (Camb)2017;53:6828-31

[89] Hou H,Yang H.Visible-light mediated hydrosilylative and hydrophosphorylative cyclizations of enynes and dienes.Org Lett2020;22:1748-53

[90] Huang WB,Wang MW,Chen KH.Cu(II)-catalyzed phosphonocarboxylative cyclization reaction of propargylic amines and phosphine oxide with CO₂.J Org Chem2020;85:14109-20

[91] Liu XC,Liu Y.Visible-light-induced metal-free synthesis of 2-phosphorylated thioflavones in water.ChemSusChem2020;13:298-303

[92] Li CX,Yao R,Lu CS.Visible-light-induced cascade reaction of isocyanides and N-arylacrylamides with diphenylphosphine oxide via radical C-P and C-C bond formation.Org Lett2016;18:4928-31

[93] Yang W,Zhang M.Metal-free photo-induced radical C-P and C-S bond formation for the synthesis of 2-phosphoryl benzothiazoles.Chinese Chemical Letters2020;31:1313-6

[94] Liu Y,Li XY.4CzIPN-.J Am Chem Soc143:964-72

[95] Liao LL,Zhang XB.Phosphorylation of alkenyl and aryl C-O bonds via photoredox/nickel dual catalysis.Org Lett2017;19:3735-8

[96] Zhu DL,Wu Q.Visible-light-induced nickel-catalyzed P(O)-C(sp²) coupling using thioxanthen-9-one as a photoredox catalysis.Org Lett2021;23:160-5

[97] Hou H,Wang J.Visible-light-induced ligand to metal charge transfer excitation enabled phosphorylation of aryl halides.Chem Commun (Camb)2021;57:5702-5

[98] Tang L,Sun T.Solvent-controlled copper-catalyzed radical decarboxylative coupling for alkenyl C(sp ² )-P bond formation.Asian J Org Chem2017;6:1683-92

[99] Xue JF,Liu YY,Zou JP.Manganese(III)-mediated alkenyl C(sp2)-P bond formation from the reaction of β-nitrostyrenes with dialkyl phosphites.Org Biomol Chem2015;13:4896-902

[100] Yuan J,Mao P.Silver-catalyzed synthesis of 2-arylvinylphosphonates by cross-coupling of β-nitrostyrenes with H-phosphites.RSC Adv2016;6:87058-65

[101] Zhou P,Zou J.Manganese(III) acetate mediated free-radical phosphonylation of flavones and coumarins.Synthesis2012;44:1043-50

[102] Yuan J,Yang L.Silver-catalyzed direct Csp2-H radical phosphorylation of coumarins with H-phosphites.Tetrahedron2015;71:8178-86

[103] Yu X,Zhang Y,Wang D.Silver-Mediated Phosphonylation of C(sp²)-H Bonds with P-H bonds: Direct C-H functionalization of ferrocenyl anilides and dialkyl phosphites under palladium- and copper-free conditions.Asian J Org Chem2016;5:1253-9

[104] Luo K,Yang WC,Wu L.Cross-coupling hydrogen evolution by visible light photocatalysis toward C(sp(2))-P FOrmation: metal-free C-H functionalization of thiazole derivatives with diarylphosphine oxides.Org Lett2016;18:452-5

[105] Qiao H,Zhang Y.Merging photoredox catalysis with transition metal catalysis: site-selective C4 or C5-H phosphonation of 8-aminoquinoline amides.Org Chem Front2017;4:1981-6

[106] Xiong Y,Qi L,Zhang J.Photocatalytic synthesis of diphosphorous quinoline compounds.Asian J Org Chem2020;9:292-5

[107] Li K,Xu K,Sun B.Electrochemically dehydrogenative C-H/P-H cross-coupling: effective synthesis of phosphonated quinoxalin-2(1 H)-ones and xanthenes.Green Chem2019;21:4412-21

[108] Rawat D,Subbarayappa A.Visible-light induced phosphonation of quinoxalines and quinoxalin-2(1 H)-ones under aerobic metal-free conditions.Green Chem2020;22:6170-5

[109] Singsardar M,Sarkar R.Visible-light-induced organophotoredox-catalyzed phosphonylation of 2 H-indazoles with diphenylphosphine oxide.J Org Chem2018;83:12694-701

[110] Gao F,Chen XL.Visible-light-induced phosphorylation of imidazo-fused heterocycles under metal-free conditions.J Org Chem2020;85:14744-52

[111] Lei T,Cheng YY,Tung CH.Cobaloxime catalysis for enamine phosphorylation with hydrogen evolution.Org Lett2020;22:5385-9

[112] Li L,Chen L,Ma X.Silver-catalyzed oxidative C(sp³)-P bond formation through C-C and P-H bond cleavage.Angew Chem Int Ed Engl2017;56:10539-44

[113] Ou Y,Liu Y.Iron-Catalyzed and Air-Mediated C(sp³)-H phosphorylation of 1,3-dicarbonyl compounds involving C-C bond cleavage.Adv Synth Catal2020;362:5783-7

[114] Zhao X,Li Y,Kim JK.Stepwise photosensitized C(sp³)-C(CO) bond cleavage and C-P bond formation of 1,3-dicarbonyls with arylphosphine oxides.Org Chem Front2019;6:1433-7

[115] Ou Y,He Z.A phosphoryl radical-initiated Atherton-Todd-type reaction under open air.Chem Commun (Camb)2020;56:1357-60

[116] Zhang H,Lin Y.Visible light photoredox catalyzed thiophosphate synthesis using methylene blue as a promoter.Org Chem Front2018;5:1416-22

[117] Dong X,Jin W.Electrochemical oxidative dehydrogenative phosphorylation of N-heterocycles with P(O)-H compounds in imidazolium-based ionic liquid.Org Lett2020;22:3062-6