31.40.3 Arylphosphinic Acids and Derivatives (Update 2018)

D. Virieux; J.-L. Pirat; J.-N. Volle

Abstract

This chapter is an update to Section 31.40 and describes published methods for the synthesis of arylphosphinic acids and derivatives reported from 2007 to early 2016. Reports on the syntheses of arylphosphinic acids and derivatives are limited to arylphosphinic acids and arylphosphinates [Ar¹R¹P(O)OH and Ar¹R¹P(O)OR², respectively], for which R¹ and R² are a hydrogen atom or any kind of hydrocarbon substituent (e.g., alkyl, aryl, hetaryl).

Key words

arylphosphinic acids - arylphosphinates - phosphines - phosphonites - phosphorus - phosphine oxides - arylation - transition-metal catalysis - esterification

• 1 Noffke AL, Bongartz M, Wätjen W, Böhler P, Spingler B, Kunz PC. J. Organomet. Chem. 2011; 696: 1096

• 2 Howard-Lock HE, Lock CJL, Penny S, Turner MA. Can. J. Chem. 1989; 67: 1051

• 3 Montchamp J.-L, Dumond YR. J. Am. Chem. Soc. 2001; 123: 510

• 4 Kalek M, Stawinski J. Tetrahedron 2009; 65: 10406

• 5 Huang C, Tang X, Fu H, Jiang Y, Zhao Y. J. Org. Chem. 2006; 71: 5020

• 6 Rao H, Jin Y, Fu H, Jiang Y, Zhao Y. Chem.–Eur. J. 2006; 12: 3636

• 7 Mortier J, Moyroud J, Bennetau B, Cain PA. J. Org. Chem. 1994; 59: 4042

• 8 Figuly GD, Martin JC. J. Org. Chem. 1980; 45: 3728

• 9 Rodríguez VY, Ángel del Águila M, Iglesias MJ, Ortiz FL. Tetrahedron 2012; 68: 7355

• 10 Coudray L, Montchamp J.-L. Eur. J. Org. Chem. 2008; 4101

• 11 Coudray L, Bravo-Altamirano K, Montchamp J.-L. Org. Lett. 2008; 10: 1123

• 12 Orthaber A, Albering JH, Belaj F, Pietschnig R. J. Fluorine Chem. 2010; 131: 1025

• 13 Allefeld N, Neumann B, Stammler H.-G, Ignat’ev N, Hoge B. Chem.–Eur. J. 2015; 21: 12326

• 14 Petit C, Fécourt F, Montchamp J.-L. Adv. Synth. Catal. 2011; 353: 1883

• 15 Troupa P, Katsiouleri G, Vassiliou S. Synlett 2015; 26: 2714

• 16 Arbuzova SN, Gusarova NK, Verkhoturova SI, Kazantseva TI, Ushakov IA, Mal’kina AG, Trofimov BA. Heteroat. Chem. 2015; 26: 231

• 17 Ballester J, Gatignol J, Schmidt G, Alayrac C, Gaumont A.-C, Taillefer M. ChemCatChem 2014; 6: 1549

• 18 Golla M, Syed R, Katla VR, Devineni SR, Kondapalli N, Chamarthi NR. J. Chem. Sci. (Berlin, Ger.) 2014; 126: 117

• 19 Subramanyam Ch, Madhava G, Thaslim Basha SK, Rasheed S, Uday Sankar A, Naga Raju C. Phosphorus, Sulfur Silicon Relat. Elem. 2015; 190: 1948

• 20 Yoshida S, Hosoya T. Chem. Lett. 2013; 42: 583

• 21 Dhokale RA, Mhaske SB. Org. Lett. 2013; 15: 2218

• 22 Dabkowski W, Ozarek A, Olejniczak S, Cypryk M, Chojnowski J, Michalski J. Chem.–Eur. J. 2009; 15: 1747

• 23 Chojnowski J, Cypryk M, Michalski J. J. Organomet. Chem. 1981; 215: 355

• 24 Krutikova VV, Krutikov VI, Erkia AV. Russ. J. Gen. Chem. (Engl. Transl.) 2010; 80: 428

• 25 Krutikov VI, Semenova ES, Maslennikov IG, Lavrent’ev AN. Zh. Obshch. Khim. 1983; 53: 1557

• 26 Burnaeva LM, Mironov VF, Abdrakhmanova LM, Gubaidullin AT, Musin RZ, Ivkova GA, Litvinov IA, Latypov ShK, Balandina AA, Konovalova IV. Russ. J. Gen. Chem. (Engl. Transl.) 2007; 77: 538

• 27 Mironov VF, Borisova YuYu, Burnaeva LM, Gubaidullin AT, Dobrynin AB, Litvinov IA, Musin RZ, Konovalova IV. Russ. Chem. Bull. 2010; 59: 820

• 28 Mironov VF, Abdrakhmanova LM, Dimukhametov MN, Burnaeva LM, Kotorova YuYu, Konovalova IV. Phosphorus, Sulfur Silicon Relat. Elem. 2008; 183: 425

• 29 Goldeman W, Soroka M. Synthesis 2010; 2437

• 30 Adamek J, Październiok-Holewa A, Zielińska K, Mazurkiewicz R. Phosphorus, Sulfur Silicon Relat. Elem. 2013; 188: 967

• 31 Październiok-Holewa A, Adamek J, Mazurkiewicz R, Zielińska K. Phosphorus, Sulfur Silicon Relat. Elem. 2013; 188: 205

• 32 Wang Y, Gan J, Liu L, Yuan J, Gao Y, Liu Y, Zhao Y. J. Org. Chem. 2014; 79: 3678

• 33 Guillouzic A.-F, Montel S, Laborde C, Volle J.-N, Pirat J.-L, Virieux D. Eur. J. Org. Chem. 2014; 788

• 34 Qureshi A, Hay AS. J. Chem. Res., Synop. 1998; 355

• 35 Řezníček T, Dostál L, Růžička A, Jirásko R, Jambor R. Inorg. Chim. Acta 2010; 363: 3302

• 36 Beletskaya IP, Karlstedt NB, Nifant’ev EE, Khodarev DV, Kukhareva TS, Nikolaev AV, Ross AJ. Russ. J. Org. Chem. (Engl. Transl.) 2006; 42: 1780

• 37 Khodarev DV, Kukhareva TS, Lipovstin EV, Nifant’ev EE. Russ. J. Gen. Chem. (Engl. Transl.) 2006; 76: 198

• 38 Wang W.-M, Liu L.-J, Zhao C.-Q, Han L.-B. Eur. J. Org. Chem. 2015; 2342

• 39 Li B, Cai S, Du D.-M, Xu J. Org. Lett. 2007; 9: 2257

• 40 Meng F, Xu J. Amino Acids 2010; 39: 533

• 41 Meng F, Xu J. Tetrahedron 2013; 69: 4944

• 42 Meng F, He F, Song X, Zhang L, Hu W, Liu G, Xu J. Amino Acids 2012; 43: 423

• 43 Bravo-Altamirano K, Huang Z, Montchamp J.-L. Tetrahedron 2005; 61: 6315

• 44 Delbianco M, Lamarque L, Parker D. Org. Biomol. Chem. 2014; 12: 8061

• 45 Bravo-Altamirano K, Coudray L, Deal EL, Montchamp J.-L. Org. Biomol. Chem. 2010; 8: 5541

• 46 Binyamin I, Meidan-Shani S, Ashkenazi N. Beilstein J. Org. Chem. 2015; 11: 1332

• 47 Gavara L, Gelat F, Montchamp J.-L. Tetrahedron Lett. 2013; 54: 817

• 48 Han ZS, Goyal N, Herbage MA, Sieber JD, Qu B, Xu Y, Li Z, Reeves JT, Desrosiers J.-N, Ma S, Grinberg N, Lee H, Mangunuru HPR, Zhang Y, Krishnamurthy D, Lu BZ, Song JJ, Wang G, Senanayake CH. J. Am. Chem. Soc. 2013; 135: 2474

• 49 Copey L, Jean-Gérard L, Framery E, Pilet G, Robert V, Andrioletti B. Chem.–Eur. J. 2015; 21: 9057

• 50 D’Onofrio A, Copey L, Jean-Gérard L, Goux-Henry C, Pilet G, Andrioletti B, Framery E. Org. Biomol. Chem. 2015; 13: 9029

• 51 Deal EL, Petit C, Montchamp J.-L. Org. Lett. 2011; 13: 3270

• 52 Montel S, Midrier C, Volle J.-N, Braun R, Haaf K, Willms L, Pirat J.-L, Virieux D. Eur. J. Org. Chem. 2012; 3237

• 53 Yang L, Xu L, Tao Z. Phosphorus, Sulfur Silicon Relat. Elem. 2009; 184: 3175

• 54 Berger O, Montchamp J.-L. Angew. Chem. Int. Ed. 2013; 52: 11377

• 55 Jablonkai E, Balázs LB, Keglevich G. Phosphorus, Sulfur Silicon Relat. Elem. 2015; 190: 660

• 56 Keglevich G, Jablonkai E, Balázs LB. RSC Adv. 2014; 4: 22808

• 57 Jablonkai E, Keglevich G. Tetrahedron Lett. 2013; 54: 4185

• 58 Tran G, Gomez Pardo D, Tsuchiya T, Hillebrand S, Vors J.-P, Cossy J. Org. Lett. 2013; 15: 5550

• 59 Berger O, Petit C, Deal EL, Montchamp J.-L. Adv. Synth. Catal. 2013; 355: 1361

• 60 Huang Q, Tran G, Gomez Pardo D, Tsuchiya T, Hillebrand S, Vors J.-P, Cossy J. Tetrahedron 2015; 71: 7250

• 61 Fu WC, So CM, Kwong FY. Org. Lett. 2015; 17: 5906

• 62 Jiang W, Allan G, Fiordeliso JJ, Linton O, Tannenbaum P, Xu J, Zhu P, Gunnet J, Demarest K, Lundeen S, Sui Z. Bioorg. Med. Chem. 2006; 14: 6726

• 63 Fu T, Qiao H, Peng Z, Hu G, Wu X, Gao Y, Zhao Y. Org. Biomol. Chem. 2014; 12: 2895

• 64 Xu W, Hu G, Xu P, Gao Y, Yin Y, Zhao Y. Adv. Synth. Catal. 2014; 356: 2948

• 65 Wang T, Sang S, Liu L, Qiao H, Gao Y, Zhao Y. J. Org. Chem. 2014; 79: 608

• 66 Zhang X, Liu H, Hu X, Tang G, Zhu J, Zhao Y. Org. Lett. 2011; 13: 3478

• 67 Kinbara A, Ito M, Abe T, Yamagishi T. Tetrahedron 2015; 71: 7614

• 68 Shen C, Yang G, Zhang W. Org. Biomol. Chem. 2012; 10: 3500

• 69 Hu G, Chen W, Fu T, Peng Z, Qiao H, Gao Y, Zhao Y. Org. Lett. 2013; 15: 5362

• 70 Yang J, Chen T, Han L.-B. J. Am. Chem. Soc. 2015; 137: 1782

• 71 Xiong B, Li M, Liu Y, Zhou Y, Zhao C, Goto M, Yin S.-F, Han L.-B. Adv. Synth. Catal. 2014; 356: 781

• 72 Xu J, Zhang P, Gao Y, Chen Y, Tang G, Zhao Y. J. Org. Chem. 2013; 78: 8176

• 73 Zhou A.-X, Mao L.-L, Wang G.-W, Yang S.-D. Chem. Commun. (Cambridge) 2014; 50: 8529

• 74 Miao W, Gao Y, Li X, Gao Y, Tang G, Zhao Y. Adv. Synth. Catal. 2012; 354: 2659

• 75 He Y, Wu H, Toste FD. Chem. Sci. 2015; 6: 1194

• 76 Yang G, Shen C, Quan M, Zhang W. Tetrahedron 2016; 72: 333

• 77 Zhang H.-J, Lin W, Wu Z, Ruan W, Wen T.-B. Chem. Commun. (Cambridge) 2015; 51: 3450

• 78 Zhang B, Daniliuc CG, Studer A. Org. Lett. 2014; 16: 250

• 79 Cao J.-J, Zhu T.-H, Gu Z.-Y, Hao W.-J, Wang S.-Y, Ji S.-J. Tetrahedron 2014; 70: 6985

• 80 Park Y, Jeon I, Shin S, Min J, Lee PH. J. Org. Chem. 2013; 78: 10209

• 81 Park Y, Seo J, Park S, Yoo EJ, Lee PH. Chem.–Eur. J. 2013; 19: 16461

• 82 Unoh Y, Hashimoto Y, Takeda D, Hirano K, Satoh T, Miura M. Org. Lett. 2013; 15: 3258

• 83 Fisher HC, Berger O, Gelat F, Montchamp J.-L. Adv. Synth. Catal. 2014; 356: 1199

• 84 Dhawan B, Redmore D. J. Org. Chem. 1986; 51: 179

• 85 Huszthy P, Farkas V, Tóth T, Székely G, Hollósi M. Tetrahedron 2008; 64: 10107

• 86 Szabó T, Hirsch E, Tóth T, Müller J, Riethmüller E, Balogh GT, Huszthy P. Tetrahedron: Asymmetry 2015; 26: 650

• 87 Petrov KA, Agafonov SV, Pokatun VP. Zh. Obshch. Khim. 1987; 57: 98

• 88 Heinicke J, Jux U, Kadyrov R, He M. Heteroat. Chem. 1997; 8: 383

• 89 Itoh H, Yamamoto E, Masaoka S, Sakai K, Tokunaga M. Adv. Synth. Catal. 2009; 351: 1796

• 90 Casimiro M, Roces L, García-Granda S, Iglesias MJ, López Ortiz F. Org. Lett. 2013; 15: 2378

• 91 Nune SK, Tanaka M. Chem. Commun. (Cambridge) 2007; 2858

• 92 Niu M, Fu H, Jiang Y, Zhao Y. Chem. Commun. (Cambridge) 2007; 272

• 93 Stockland RA, Lipman AJ, Bawiec III JA, Morrison PE, Guzei IA, Findeis PM, Tamblin JF. J. Organomet. Chem. 2006; 691: 4042

• 94 Xu Q, Shen R, Ono Y, Nagahata R, Shimada S, Goto M, Han L.-B. Chem. Commun. (Cambridge) 2011; 47: 2333

• 95 Trostyanskaya IG, Beletskaya IP. Tetrahedron 2014; 70: 2556

• 96 Hu G, Gao Y, Zhao Y. Org. Lett. 2014; 16: 4464

• 97 Salin AV, Il’in AV, Shamsutdinova FG, Fatkutdinov AR, Galkin VI, Islamov DR, Kataeva ON. Tetrahedron Lett. 2015; 56: 6282

• 98 Hu J, Zhao N, Yang B, Wang G, Guo L.-N, Liang Y.-M, Yang S.-D. Chem.–Eur. J. 2011; 17: 5516

• 99 Mao L.-L, Zhou A.-X, Liu N, Yang S.-D. Synlett 2014; 25: 2727

• 100 Wu Y, Liu L, Yan K, Xu P, Gao Y, Zhao Y. J. Org. Chem. 2014; 79: 8118

• 101 Liu L, Wang Y, Zeng Z, Xu P, Gao Y, Yin Y, Zhao Y. Adv. Synth. Catal. 2013; 355: 659

• 102 Ye J, Ma S. Acc. Chem. Res. 2014; 47: 989

• 103 Ma S. Chem. Rev. 2005; 105: 2829

• 104 Yu S, Ma S. Angew. Chem. Int. Ed. 2012; 51: 3074

• 105 Kalek M, Johansson T, Jezowska M, Stawinski J. Org. Lett. 2010; 12: 4702

• 106 Kalek M, Stawinski J. Adv. Synth. Catal. 2011; 353: 1741

• 107 Zhou Y, Wang S, Chen C, Xi C. RSC Adv. 2015; 5: 71724

• 108 Takahashi T, Xi C, Xi Z, Kageyama M, Fischer R, Nakajima K, Negishi E.-I. J. Org. Chem. 1998; 63: 6802

• 109 Yang J, Chen T, Zhou Y, Yin S, Han L.-B. Chem. Commun. (Cambridge) 2015; 51: 3549

• 110 Yang J, Chen T, Zhou Y, Yin S.-F, Han L.-B. Organometallics 2015; 34: 5095

• 111 Gao Y, Wang G, Chen L, Xu P, Zhao Y, Zhou Y, Han L.-B. J. Am. Chem. Soc. 2009; 131: 7956

• 112 Wang T, Chen S, Shao A, Gao M, Huang Y, Lei A. Org. Lett. 2015; 17: 118

• 113 Zhdankin VV, Stang PJ. Tetrahedron 1998; 54: 10927

• 114 Chen CC, Waser J. Chem. Commun. (Cambridge) 2014; 50: 12923

• 115 Wu J, Gao Y, Zhao X, Zhang L, Chen W, Tang G, Zhao Y. RSC Adv. 2016; 6: 303

• 116 Ortial S, Fisher HC, Montchamp J.-L. J. Org. Chem. 2013; 78: 6599

• 117 Li Z, Fan F, Zhang Z, Xiao Y, Liu D, Liu Z.-Q. RSC Adv. 2015; 5: 27853

• 118 Richard V, Fisher HC, Montchamp J.-L. Tetrahedron Lett. 2015; 56: 3197

• 119 Gao Y, Li X, Xu J, Wu Y, Chen W, Tang G, Zhao Y. Chem. Commun. (Cambridge) 2015; 51: 1605

• 120 Chu X.-Q, Zi Y, Meng H, Xu X.-P, Ji S.-J. Chem. Commun. (Cambridge) 2014; 50: 7642

• 121 Saga Y, Han D, Kawaguchi S.-I, Ogawa A, Han L.-B. Tetrahedron Lett. 2015; 56: 5303

• 122 Gao Y, Li X, Chen W, Tang G, Zhao Y. J. Org. Chem. 2015; 80: 11398

• 123 Hirai T, Han L.-B. Org. Lett. 2007; 9: 53

• 124 Soeta T, Matsuzaki S, Ukaji Y. Chem.–Eur. J. 2014; 20: 5007

• 125 Masuda Y, Ishida N, Murakami M. Chem.–Asian J. 2015; 10: 321

• 126 Zhou Y, Zhou M, Chen M, Su J, Du J, Song Q. RSC Adv. 2015; 5: 103977

• 127 Zhou M, Zhou Y, Song Q. Chem.–Eur. J. 2015; 21: 10654

• 128 Wie W, Ji J.-X. Angew. Chem. Int. Ed. 2011; 50: 9097

• 129 Li X, Hu G, Luo P, Tang G, Gao Y, Xu P, Zhao Y. Adv. Synth. Catal. 2012; 354: 2427

• 130 Zhou M, Chen M, Zhou Y, Yang K, Su J, Du J, Song Q. Org. Lett. 2015; 17: 1786

• 131 Chen X, Li X, Chen X.-L, Qu L.-B, Chen J.-Y, Sun K, Liu Z.-D, Bi W.-Z, Xia Y.-Y, Wu H.-T, Zhao Y.-F. Chem. Commun. (Cambridge) 2015; 51: 3846

• 132 Ke J, Tang Y, Yi H, Li Y, Cheng Y, Liu C, Lei A. Angew. Chem. Int. Ed. 2015; 54: 6604

• 133 Kanada J, Yamashita K.-I, Nune SK, Tanaka M. Tetrahedron Lett. 2009; 50: 6196

• 134 Eom D, Jeong Y, Kim YR, Lee E, Choi W, Lee PH. Org. Lett. 2013; 15: 5210

• 135 Kiss NZ, Ludányi K, Drahos K, Keglevich G. Synth. Commun. 2009; 39: 2392

• 136 Xiong B, Ye Q, Feng X, Zhu L, Chen T, Zhou Y, Au C.-T, Yin S.-F. Tetrahedron 2014; 70: 9057

• 137 Jablonkai E, Henyecz R, Milen M, Kóti J, Keglevich G. Tetrahedron 2014; 70: 8280

• 138 Liu N, Mao L.-L, Yang B, Yang S.-D. Chem. Commun. (Cambridge) 2014; 50: 10879

• 139 Arisawa M, Kuwajima M, Yamaguchi M. Tetrahedron Lett. 2010; 51: 3116

• 140 Li S, Chen T, Saga Y, Han L.-B. RSC Adv. 2015; 5: 71544

• 141 Liu C, Wei W, Yang D, Zheng Y, Bi Y, Chen M, Wang H. Tetrahedron 2015; 71: 6901

• 142 Xu J, Zhang P, Li X, Gao Y, Wu J, Tang G, Zhao Y. Adv. Synth. Catal. 2014; 356: 3331

• 143 Hubacz A, Makowiec S. Heteroat. Chem. 2009; 20: 81

• 144 Jankowski S, Kovács J, Huben K, Blaszczyk M, Główka M, Keglevich G. Heteroat. Chem. 2006; 17: 369

• 145 Xiong B, Feng X, Zhu L, Chen T, Zhou Y, Au C.-T, Yin S.-F. ACS Catal. 2015; 5: 537

• 146 Berger O, Gavara L, Montchamp J.-L. Org. Lett. 2012; 14: 3404