Donohoe, T. J. et al.: 2022 Science of Synthesis, 2022/1: Knowledge Updates 2022/1 DOI: 10.1055/sos-SD-142-00235
Knowledge Updates 2022/1

42.18.2 Pentacoordinated Phosphoranes (Update 2022)

More Information

Book

Editors: Donohoe, T. J.; Krause, N.; Marsden, S. P.; Montchamp, J.-L.; Terent'ev, A. O. ; Weinreb, S. M.

Authors: Ayad, T. ; Barsegyan, Y. ; de Lucca, Jr., E. C. ; Haake, E. ; Hutskalova, V. ; Jux, N. ; Montforts, F.-P. ; Munaretto, L. S. ; Pajkert, R. ; Pirat, J.-L. ; Röschenthaler, G.-V. ; Santana, V. C. S. ; Terent'ev, A. O. ; Tius, M. A. ; Tomkinson, N. C. O. ; Sparr, C. ; Vil’, V. A. ; Virieux, D.

Title: Knowledge Updates 2022/1

Print ISBN: 9783132451476; Online ISBN: 9783132451490; Book DOI: 10.1055/b000000641

Subjects: Organic Chemistry;Chemical Reactions, Catalysis;Organometallic Chemistry;Laboratory Techniques, Stoichiometry

Science of Synthesis Knowledge Updates



Parent publication

Title: Science of Synthesis

DOI: 10.1055/b-00000101

Series Editors: Fürstner, A. (Editor-in-Chief); Carreira, E. M.; Faul, M.; Kobayashi, S.; Koch, G.; Molander, G. A.; Nevado, C.; Trost, B. M.; You, S.-L.

Type: Multivolume Edition

 


Abstract

This is an update to the previous Science of Synthesis chapter on pentacoordinated phosphoranes (Section 42.18), and covers methods for their synthesis and application published up to 2020. Due to the fact that the past years have seen a considerable number of papers including spirocyclic phosphoranes, reports on the synthesis have been limited to selected spirophosphoranes such as spirohydrophosphoranes, caged phosphoranes, or metallophosphoranes. In addition, some classical examples of the preparation of these types of compound are also discussed in this review.

 
  • 1 Burgada R. Phosphorus Sulfur Relat. Elem. 1976; 2: 237
  • 2 Burgada R, Setton R, In: The Chemistry of Organophosphorus Compounds Hartley F. Wiley Chichester 1994; 3. 185
  • 3 Głowiak T, Rybak WK, Skarżyńska A. Polyhedron 2000; 19: 2667
  • 4 Yu L, Liu Z, Fang H, Zeng QL, Zhao YF. Amino Acids 2005; 28: 369
  • 5 Hou J.-B, Zhang H, Guo J.-N, Liu Y, Xu P.-X, Zhao Y.-F, Blackburn GM. Org. Biomol. Chem. 2009; 7: 3020
  • 6 Mamula O, Von Zalewsky A, Bark T, Stoekli-Evans H, Neels A, Bernardinelli G. Chem.–Eur. J. 2000; 6: 3575
  • 7 Ross MR, Martin JC. J. Am. Chem. Soc. 1981; 103: 1234
  • 8 Jiang X.-D, Kakuda K.-i, Matsukawa S, Yamamichi H, Kojima S, Yamamoto Y. Chem.–Asian J. 2007; 2: 314
  • 9 Jiang X.-D, Matsukawa S, Yamamichi H, Yamamoto Y. Heterocycles 2007; 73: 805
  • 10 Jiang X.-D, Matsukawa S, Kakuda K.-i, Fukuzaki Y, Zhao W.-L, Li L.-S, Shen H.-B, Kojima S, Yamamoto Y. Dalton Trans. 2010; 39: 9823
  • 11 Van Lier JJC, Hermans RJM, Buck HM. Phosphorus Sulfur Relat. Elem. 1984; 19: 173
  • 12 Gavrilov KN, Teleshev AT, Nifantyev EE. J. Organomet. Chem. 1993; 461: 233
  • 13 Storzer W, Röschenthaler G.-V, Schmutzler R, Sheldrick WS. Chem. Ber. 1981; 114: 3609
  • 14 Schomburg D, Storzer W, Bohlen R, Kuhn W, Röschenthaler G.-V. Chem. Ber. 1983; 116: 3301
  • 15 Skarżyńska A, Gniewek A. Inorg. Chim. Acta 2018; 483: 248
  • 16 Han L.-B, Ono Y, Shimada S. Bull. Chem. Soc. Jpn. 2010; 83: 1086
  • 17 Mizrakh LI, Polonskaya LYu, Gvozdetskii AN, Vasil'ev AM. Zh. Obshch. Khim. 1986; 56: 73
  • 18 Polosukhin AI, Kovalevsky AY, Korostylev AV, Davankov VA, Gavrilov KN. Phosphorus, Sulfur Silicon Relat. Elem. 2000; 159: 69
  • 19 Gavrilov KN, Korostylev AV, Polosukhin AI, Bondarev OG, Kovalevsky AY, Davankov VA. J. Organomet. Chem. 2000; 613: 148
  • 20 Polyancev FM, Metlushka KE, Sadkova DN, Khisametdinova ZR, Kataeva ON, Alfonsov VA, Latypov SK, Sinyashin OG. Dalton Trans. 2017; 46: 8146
  • 21 Pudovik AN, Konovalova IV, Burnaeva LM. Synthesis 1986; 793
  • 22 Abdrakhmanova LM, Mironov VF, Dimukhametov MN, Krivolapov DB, Litvinov IA. Mendeleev Commun. 2010; 20: 41
  • 23 Mironov VF, Dimukhametov MN, Mironova EV, Krivolapov DB, Ivkova GA, Abdrakhmanova LM. Russ. J. Gen. Chem. (Engl. Transl.) 2015; 85: 450
  • 24 Abdrakhmanova LM, Mironov VF, Baronova TA, Krivolapov DB, Litvinov IA, Dimukhametov MN, Musin RZ, Konovalov AI. Russ. Chem. Bull. 2008; 57: 1559
  • 25 Mironov VF, Dimukhametov MN, Mironova EV, Krivolapov DB, Abdrakhmanova LM. Russ. J. Gen. Chem. (Engl. Transl.) 2015; 85: 441
  • 26 Muetterties EL, Bither TA, Farlow MW, Coffman DD. J. Inorg. Nucl. Chem. 1960; 16: 52
  • 27 Dillon KB, Waddington TC. Chem. Commun. 1969; 1317
  • 28 Granoth I, Martin JC. J. Am. Chem. Soc. 1979; 101: 4623
  • 29 Baudler M. Angew. Chem. Int. Ed. Engl. 1987; 26: 419
  • 30 Baudler M, Riekehofbohmer R, Hahn J. Z. Anorg. Allg. Chem. 1987; 547: 149
  • 31 Kojima S, Kajiyama K, Akiba K.-y. Bull. Chem. Soc. Jpn. 1995; 68: 1785
  • 32 Akiba K.-y, Matsukawa S, Kajiyama K, Nakamoto M, Kojima S, Yamamoto Y. Heteroat. Chem. 2002; 13: 390
  • 33 Kano N, Miyake H, Kawashima T. Chem. Lett. 2007; 36: 1260
  • 34 Miyake H, Kano N, Kawashima T. Phosphorus, Sulfur Silicon Relat. Elem. 2008; 183: 673
  • 35 Kajiyama K, Fujimori S, Yasuoka D, Otsuka T. Tetrahedron 2013; 69: 9155
  • 36 Skarżyńska A. Coord. Chem. Rev. 2013; 257: 1039
  • 37 Wachter J, Mentzen BF, Riess JG. Angew. Chem. Int. Ed. Engl. 1981; 20: 284
  • 38 Lattman M, Morse SA, Cowley AH, Lasch JG, Norman NC. Inorg. Chem. 1985; 24: 1364
  • 39 Kubo K, Nakazawa H, Ogitani Y, Miyoshi K. Bull. Chem. Soc. Jpn. 2001; 74: 1411
  • 40 Lattman M, Anand BN, Garett DR, Whitener MA. Inorg. Chim. Acta 1983; 76: L139
  • 41 Faw R, Montgomery CD, Rettig SJ, Shurmer B. Inorg. Chem. 1998; 37: 4136
  • 42 Kajiyama K, Yuge H, Miyamoto TK. Phosphorus, Sulfur Silicon Relat. Elem. 2002; 177: 1433
  • 43 Nakazawa H, Kubo K, Miyoshi K. J. Am. Chem. Soc. 1993; 115: 5863
  • 44 Kubo K, Nakazawa H, Mizuta T, Miyoshi K. Organometallics 1998; 17: 3522
  • 45 Berry RS. J. Chem. Phys. 1960; 32: 933
  • 46 Muetterties EL, Mahler W, Schmutzler R. Inorg. Chem. 1963; 2: 613
  • 47 Kojima S, Nakata M, Yamazaki K, Akiba K.-y. Tetrahedron Lett. 1997; 38: 4107
  • 48 Nakamoto M, Kojima S, Matsukawa S, Yamamoto Y, Akiba K.-y. J. Organomet. Chem. 2002; 643: 441
  • 49 Atherton FR, Openshaw HT, Todd AR. J. Chem. Soc. 1945; 660
  • 50 Atherton FR, Todd AR. J. Chem. Soc. 1947; 674
  • 51 Steinberg GM. J. Org. Chem. 1950; 15: 637
  • 52 Han L.-B, Zhao C.-Q. J. Org. Chem. 2005; 70: 10 121
  • 53 Bounja Z, Houalla D, Revel M. Phosphorus, Sulfur Silicon Relat. Elem. 1992; 69: 43
  • 54 Cao S, Gao P, Guo Y, Zhao H, Wang J, Liu Y, Zhao Y. J. Org. Chem. 2013; 78: 11 283
  • 55 Cao S, Guo Y, Wang J, Qi L, Gao P, Zhao H, Zhao Y. Tetrahedron Lett. 2012; 53: 6302
  • 56 Dai W, Liu Q, You X, Zhou Z, Guo Y, Zhao Y, Cao S. Heteroat. Chem. 2016; 27: 63
  • 57 Jiang X.-D, Matsukawa S, Yamamoto Y. Dalton Trans. 2008; 3678
  • 58 Jiang X.-D, Matsukawa S, Yamamichi H, Yamamoto Y. Heterocycles 2007; 73: 805
  • 59 Adachi T, Matsukawa S, Nakamoto M, Kajiyama K, Kojima S, Yamamoto Y, Akiba K.-y, Re S, Nagase S. Inorg. Chem. 2006; 45: 7269