[1]
Hirao, T.; Masunaga, T.; Ohshiro, Y.; Agawa, T. Stereoselective synthesis of vinylphosphonate. Tetrahedron Lett., 1980, 21, 3595-3598.
[2]
Hirao, T.; Masunaga, T.; Yamada, N.; Ohshiro, Y.; Agawa, T. Palladium-catalyzed new carbon-phosphorus bond formation. Bull. Chem. Soc. Jpn., 1982, 55, 909-913.
[3]
Jablonkai, E.; Keglevich, G. P-C bond formation by coupling reaction utilizing >P(O)H species as the reagents. Curr. Org. Synth., 2014, 11, 429-453.
[4]
Jablonkai, E.; Keglevich, G. Advances and new variations of the Hirao reaction. Org. Prep. Proced. Int., 2014, 46, 281-316.
[5]
Shen, C.; Yang, G.; Zhang, W. Nickel-catalyzed C-P coupling of aryl mesylates and tosylates with H(O)PR1R2. Org. Biomol. Chem., 2012, 10, 3500-3505.
[6]
Zhang, X.; Liu, H.; Hu, X.; Tang, G.; Zhu, J.; Zhao, Y. Ni(II)/Zn catalyzed reductive coupling of aryl halides with diphenylphosphine oxide in water. Org. Lett., 2011, 13, 3478-3481.
[7]
Cai, D.; Payack, J.F.; Bender, D.R.; Hughes, D.L.; Verhoeven, T.R.; Reider, P.J. Synthesis of chiral 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (BINAP) via a novel nickel-catalyzed phosphine insertion. J. Org. Chem., 1994, 59, 7180-7181.
[8]
Gladiali, S.; Pulacchini, S.; Fabbri, D.; Manassero, M.; Sansoni, M. 2-Diphenylphosphino-2′-diphenylphospinyl-1,1′-binaphthalene (BINAPO), an axially chiral heterobidentate ligand for enantioselective catalysis. Tetrahedron Asymmetry, 1998, 9, 391-395.
[9]
Gladiali, S.; Taras, R.; Ceder, R.M.; Rocamora, M.; Muller, G.; Solans, X.; Font-Bardia, M. Asymmetric allylic alkylation catalyzed by Pd(II)-complexes with (S)-BINPO, a hemilabile axially chiral P,O-heterodonor inducer. Tetrahedron Asymmetry, 2004, 15, 1477-1485.
[10]
Zhao, Y.L.; Wu, G.J.; Li, Y.; Gao, L.X.; Han, F.S. [NiCl2(dppp)]-catalyzed cross-coupling of aryl halides with dialkyl phosphite, diphenylphosphine oxide and diphenylphosphine. Chem. Eur. J., 2012, 18, 9622-9627.
[11]
Zhao, Y.L.; Wu, G.J.; Han, F.S. Ni-catalyzed construction of C-P bonds from electron-deficient phenols via the in situ aryl C-O activation by PyBrOP. Chem. Commun., 2012, 48, 5868-5870.
[12]
Novikova, Z.S.; Demik, N.N.; Agarkov, A.Y.; Beletskaya, I.P. Palladium-catalyzed arylation of diethyl hydrogen phosphite. Russ. J. Org. Chem., 1995, 31, 129.
[13]
Kabachnik, M.M.; Solntseva, M.D.; Izmer, V.V.; Novikova, Z.S.; Beletskaya, I.P. Palladium-catalyzed phase-transfer arylation of dialkyl phosphonates. Russ. J. Org. Chem., 1998, 34, 93-97.
[14]
Kalek, M.; Ziadi, A.; Stawinski, J. Microwave-assisted palladium-catalyzed cross-coupling of aryl and vinyl halides with H-phosphonate diesters. Org. Lett., 2008, 10, 4637-4640.
[15]
Rummelt, S.M.; Ranocchiari, M.; van Bokhoven, J.A. Synthesis of water-soluble phosphine oxides by Pd/C-catalyzed P-C coupling in water. Org. Lett., 2012, 14, 2188-2190.
[16]
Jablonkai, E.; Keglevich, G. P-Ligand-free, microwave-assisted variation of the Hirao reaction under solvent-free conditions; the P-C coupling reaction of >P(O)H species and bromoarenes. Tetrahedron Lett., 2013, 54, 4185-4188.
[17]
Keglevich, G.; Jablonkai, E.; Balázs, L.B.A. “green” variation of the Hirao reaction: the P-C coupling of diethyl phosphite, alkyl phenyl-H-phosphinates and secondary phosphine oxides with bromoarenes using P-ligand-free Pd(OAc)2 catalyst under microwave and solvent-free conditions. RSC Advances, 2014, 4, 22808-22816.
[18]
Amaya, T.; Abe, Y.; Inada, Y.; Hirao, T. Synthesis of self-doped conducting polyaniline bearing phosphonic acid. Tetrahedron Lett., 2014, 55, 3976-3978.
[19]
Xiong, B.; Li, M.; Liu, Y.; Zhou, Y.; Zhao, C.; Goto, M.; Yin, S.F.; Han, L.B. Stereoselective synthesis of phosphoryl-substituted phenols. Adv. Synth. Catal., 2014, 356, 781-794.
[20]
Jablonkai, E.; Henyecz, R.; Ábrányi-Balogh, P.; Milen, M.; Kóti, J.; Drahos, L.; Keglevich, G. T3P®-assisted esterification and amidation of phosphinic acids. Tetrahedron, 2014, 70, 8280-8285.
[21]
Goto, M.; Yamano, M. Process for preparation of diphosphine compounds and intermediates for the process. Patent WO 2003048174, 2003, Chem. Abstr., 2003, 139, 36636
[22]
Xu, K.; Hu, H.; Yang, F.; Wu, Y. Synthesis of aryl and arylmethyl phosphonates by cross-coupling of aryl or arylmethyl halides (X = I, Br and Cl) with diisopropyl H-phosphonate. Eur. J. Org. Chem., 2013, 319-325.
[23]
Xu, K.; Yang, F.; Zhang, G.; Wu, Y. Palladacycle-catalyzed phosphonation of aryl halides in neat water. Green Chem., 2013, 15, 1055-1060.
[24]
Belabassi, Y.; Alzghari, S.; Montchamp, J.L. Revisiting the Hiaro cross-coupling: Improves synthesis of aryl and heteroaryl phosphonates. J. Organomet. Chem., 2008, 693, 3171-3178.
[25]
Schuman, M.; Lopez, X.; Karplus, M.; Gouverneur, V. Synthesis of a novel diarylphosphinic acid: A distorted ground state mimic and transition state analogue for amide hydrolysis. Tetrahedron, 2001, 57, 10299-10307.
[26]
Morgan, P.W.; Herr, B.C. Some dicarboxylic acids and esters containing the phosphine oxide group. J. Am. Chem. Soc., 1952, 74, 4526-4529.
[27]
Haberhauer, G.; Ernst, S.; Wilch, C. An unexpected and easy way of freezing the configuration of a triaryl phosphane oxide. Chem. Eur. J., 2011, 17, 8643-8647.
[28]
De Ketelaere, R.F.; Van der Kelen, G.P.; Eeckhaut, Z. Organophosphorus chemistry. III. Synthesis of some tertiary substituted arylphosphine oxides, sulfides, and selenides. Phosphorus Sulfur, 1974, 5, 43-45.
[29]
Hu, G.; Chen, W.; Fu, T.; Peng, Z.; Qiao, H.; Gao, Y.; Zhao, Y. Nickel-catalyzed C-P cross-coupling of arylboronic acids with P(O)H compounds. Org. Lett., 2013, 15, 5362-5365.
[30]
Yang, G.; Shen, C.; Zhang, L.; Zhang, W. Nickel-catalyzed Arbuzov reactions of aryl triflates with triethyl phosphite. Tetrahedron Lett., 2011, 52, 5032-5035.
[31]
Zhuang, R.; Xu, J.; Cai, Z.; Tang, G.; Fang, M.; Zhao, Y. Copper-catalyzed C-P bond construction via direct coupling of phenylboronic acids with H-phosphonate diesters. Org. Lett., 2011, 13, 2110-2113.
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