Abstract
The use of monodentate phosphorus ligands, such as phosphonites, phosphites and phosphoramidites, in the rhodium-catalysed asymmetric hydrogenation of a range of mostly alkene type substrates was reported for the first time in 2000. Not only are these ligands cheap and easy to prepare in one or two steps, their use has also created new opportunities, such as their robotic parallel synthesis and the use of complexes containing two different monodentate ligands, which tremendously increases the available diversity. This review covers the period between 2006 and 2016. Many new ligands have been made during this time; not only new variants on the three ligand types that were earlier reported, but also monodentate phosphines and secondary phosphine oxides. These were mostly tested on the usual N-acetyl-dehydroamino acids, itaconic esters and enamide type substrates. Other more novel substrates were N-formyl-dehydroamino acids, all the variants of the beta-dehydroamino acid family, enol esters, 2-methylidene-1,2,3,4-tetrahydro-β-carbolines, alkenes containing phosphonate or thioether substituents, several substituted acrylic acids as well as substituted cinnamic acids. The mechanism of the rhodium-catalysed hydrogenation with phosphites, phosphonites, phosphoramidites as well as phosphepines has been reported. A common theme in these mechanisms is the formation of a dimeric bimetallic complex after subjecting the [RhL2(cod)]X or [RhL2(nbd)]X (X = BF4,PF6, SbF6) complexes to hydrogen. Since these hydrogenations are usually carried out in non-polar solvents, the formation of the expected RhL2(Solvent)2 complexes does not occur after the removal of the diene and instead each rhodium atom in these dimeric complexes coordinates not only to two monodentate ligands, but also in η6 fashion to an aromatic ring of one of the ligands that is bound to the other rhodium atom. These complexes can react with the substrate to form the substrate complex that is hydrogenated. Other studies also found that it is possible to form rhodium hydride complexes first, which react with the substrate to form product. There is one well-described industrial application on large scale in which a substituted 2-isopropyl-cinnamic acid is hydrogenated using a rhodium complex with a mixture of 2 eq. of 3,3’-dimethyl-PipPhos and 1 eq. of triphenylphosphine. The addition of the non-chiral triarylphosphine not only accelerated the reaction 50-fold, also the enantioselectivity was much improved. The product was used as a building block for AliskirenTM, a blood-pressure lowering agent.
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References
Knowles WS, Sabacky MJ (1968) J Chem Soc Chem Commun 1445
Knowles WS (1983) Acc Chem Res 16:106
Horner L, Siegel H, Büthe H (1968) Angew Chem Int Ed Engl 7:942
Vineyard BD, Knowles WS, Sabacky MJ, Bachman GL, Weinkauff DJ (1977) J Am Chem Soc 99:5946
Dang TP, Kagan HB (1971) J Chem Soc Chem Commun 481
Kagan HB, Dang TP (1972) J Am Chem Soc 94:6429
Knowles WS, Sabacky MJ, Vineyard BD (1972) J Chem Soc Chem Commun 10
Claver C, Fernandez E, Gillon A, Heslop K, Hyett DJ, Martorell A, Orpen AG, Pringle PG (2000) Chem Commun 961
Reetz MT, Sell T (2000) Tetrahedron Lett 41:6333
Reetz MT, Mehler G (2000) Angew Chem Int Ed 39:3889
van den Berg M, Minnaard AJ, Schudde EP, van Esch J, de Vries AHM, de Vries JG, Feringa BL (2000) J Am Chem Soc 122:11539
Minnaard AJ, Feringa BL, Lefort L, de Vries JG (2007) Acc Chem Res 40:1267
Reetz MT, Sell T, Meiswinkel A, Mehler G (2003) Angew Chem Int Ed 42:790
Reetz MT, Mehler G (2003) Tetrahedron Lett 44:4593
Pena D, Minnaard AJ, Boogers JAF, de Vries AHM, de Vries JG, Feringa BL (2003) Org Biomol Chem 1:1087
Hoen R, Boogers JAF, Bernsmann H, Minnaard AJ, Meetsma A, Tiemersma-Wegman TD, de Vries AHM, de Vries JG, Feringa BL (2005) Angew Chem Int Ed 44:4209
Gennari C, Monti C, Piarulli U, de Vries JG, de Vries AHM, Lefort L (2005) Chem Eur J 11:6701
Reetz MT, Li X (2006) Chem Commun 2159
Lefort L, Boogers JAF, de Vries AHM, de Vries JG (2004) Org Lett 6:1733
Junge K, Oehme G, Monsees A, Riermeier T, Dingerdissen U, Beller M (2002) Tetrahedron Lett 43:4977
Enthaler S, Erre G, Junge K, Michalik D, Spannenberg A, Marras F, Gladiali S, Beller M (2007) Tetrahedron Asymmetry 18:1288
Enthaler S, Erre G, Junge K, Holz J, Börner A, Alberico E, Nieddu I, Gladiali S, Beller M (2007) Org Proc Res Dev 11:568
Gladiali S, Alberico E, Junge K, Beller M (2011) Chem Soc Rev 40:3744
Erre G, Enthaler S, Junge K, Gladiali S, Beller M (2008) Coord Chem Rev 252:471
Hu A-G, Fu Y, Xie J-H, Zhou H, Wang L-X, Zhou Q-L (2002) Angew Chem Int Ed 41:2348
Fu Y, Xie J-H, Hu A-G, Zhou H, Wang L-X, Zhou Q-L (2002) Chem Commun 480
Zhu S-F, Fu Y, Xie J-H, Liu B, Xing L, Zhou Q-L (2003) Tetrahedron Asymmetry 14:3219
Jiang X-B, Minnaard AJ, Hessen B, Feringa BL, Duchateau ALL, Andrien JGO, Boogers JAF, de Vries JG (2003) Org Lett 5:1503
Jiang X-B, van den Berg M, Minnaard AJ, Feringa BL, de Vries JG (2004) Tetrahedron Asymmetry 15:2223
Jerphagnon T, Renaud J-L, Bruneau C (2004) Tetrahedron Asymmetry 15:2101
de Vries JG (2005) In: Ager DJ (ed) Handbook of chiral chemicals, 2nd edn. CRC Press, Boca Raton, pp 269–286
van den Berg M, Feringa BL, Minnaard AJ (2007) In: de Vries JG, Elsevier CJ (eds) Handbook of homogeneous hydrogenation, vol 2. Wiley-VCH, Weinheim, p 995
Bondarev OG, Goddard R (2006) Tetrahedron Lett 47:9013
Eberhardt L, Armspach D, Matt D, Toupet L, Oswald B (2007) Eur J Org Chem 5395
Lyubimov SE, Davankov VA, Valetskii PM, Petrovskii PV, Maksimova MG, Gavrilov KN (2006) Russ Chem Bull Int Ed 55:1448
Liu Y, Ding K, Am J (2005) Chem Soc 127:10488
Zhao B, Wang Z, Ding K (2006) Adv Synth Catal 348:1049
Liu Y, Wang Z, Ding K (2012) Tetrahedron 68:7581
Eberhardt L, Armspach D, Harrowfield J, Matt D (2008) Chem Soc Rev 37:839
Eberhardt L, Armspach D, Matt D, Toupet L, Oswald B (2007) Eur J Inorg Chem 4153
Zhu S-F, Liu T, Yang S, Song S, Zhou Q-L (2012) Tetrahedron 68:7685
Lyubimow SE, Tyutyunov AA, Kalinin VN, Said-Galiev EE, Khokhlov AR, Petrovskii PV, Davankov VA (2007) Tetrahedron Lett 48:8217
Lyubimow SE, Davankov VA, Petrovskii PV, Hey-Hawkins E, Tyutyunov AA, Rys EG, Kalinin VN (2008) J Organomet Chem 693:3689
Lyubimow SE, Kuchurov IV, Tyutyunov AA, Petrovskii PV, Kalinin VN, Zlotin SG, Davankov VA, Hey-Hawkins E (2010) Catal Commun 11:419
Lyubimow SE, Rastorguev EA, Verbitskaya TA, Petrovskii PV, Hey-Hawkins E, Kalinin VN, Davankov VA (2011) Polyhedron 30:1258
Schmitz C, Leitner W, Franciò G (2015) Eur J Org Chem 2889
Iuliano A, Losi D, Facchetti S (2007) J Org Chem 72:8472
Reetz MT, Li X (2005) Angew Chem Int Ed 44:2959
Monti C, Gennari C, Piarulli U, de Vries JG, De Vries AHM, Lefort L (2005) Chem Eur J 11:6701
Frank DJ, Franzke A, Pfaltz A (2013) Chem Eur J 19:2405
Breit B, Fuchs E (2006) Synthesis 2121
Kokan Z, Kirin SI (2013) Eur J Org Chem 8154
Hopewell J, Jankowski P, McMullin CL, Orpen AG, Pringle PG (2010) Chem Commun 46:100
Galland A, Dobrota C, Toffano M, Fiaud J-C (2006) Tetrahedron Asymmetry 17:2354
Dobrota C, Fiaud J-C, Toffano M (2015) ChemCatChem 7:144
Wang X-B, Goto M, Han L-B (2015) Chem Eur J 20:3631
Bruneau C, Renaud J-L, Jerphagnon T (2008) Coord Chem Rev 252:532
Hoen R, Tiemersma-Wegman T, Procuranti B, Lefort L, de Vries JG, Minnaard AJ, Feringa BL (2007) Org Biol Chem 5:267
Hekking KFW, Lefort L, de Vries AHM, van Delft FL, Schoemaker HE, de Vries JG, Rutjes FPJT (2008) Adv Synth Catal 350:85
Lefort L, Boogers JAF, Kuilman T, Vijn RJ, Janssen J, Straatman H, de Vries JG, De Vries AHM (2010) Org Proc Res Dev 14:568
Mršić N, Jerphagnon T, Minnaard AJ, Feringa BL, de Vries JG (2010) Tetrahedron Asymmetry 21:7
Meindertsma AF, Pollard MM, Feringa BL, de Vries JG, Minnaard AJ (2007) Tetrahedron Asymmetry 18:2849
Zhang J, Li Y, Wang Z, Ding K (2011) Angew Chem Int Ed 50:11743
Dong K, Li Y, Wang Z, Ding K (2013) Angew Chem Int Ed 52:14191
Dong K, Li Y, Wang Z, Ding K (2014) Org Chem Front 1:155
Li Y, Wang Z, Ding K (2015) Angew Chem Int Ed 21:16387
van den Berg M, Minnaard AJ, Haak RM, Leeman M, Schudde EP, Meetsma A, Feringa BL, de Vries AHM, Elizabeth C, Maljaars P, Willans CE, Hyett D, Boogers JAF, Henderickx HJW, de Vries JG (2003) Adv Synth Catal 345:308
Reetz MT, Meiswinkel A, Mehler G, Angermund K, Graf M, Thiel W, Mynott R, Blackmond DG (2005) J Am Chem Soc 127:10305
Reetz MT, Fu Y, Meiswinkel A (2006) Angew Chem Int Ed 45:1412
Gridnev ID, Fan C, Pringle PG (2007) Chem Commun 1319
Alberico E, Baumann W, de Vries JG, Drexler H-J, Gladiali S, Heller D, Henderickx HJW, Lefort L (2011) Chem Eur J 17:12683
Gridnev ID, Alberico E, Gladiali S (2012) Chem Commun 48:2186
Schiaffino L, Ercolani G (2011) J Phys Org Chem 24:257
Liu Y, Sandoval CA, Yamaguchi Y, Zhang X, Wang Z, Kato K, Ding K (2006) J Am Chem Soc 128:14212
Weis M, Waloch C, Seiche W, Breit B (2006) J Am Chem Soc 128:4188
Birkholz M-N, Dubrovina NV, Jiao H, Michalik D, Holz J, Paciello R, Breit B, Börner A (2007) Chem Eur J 13:5896
Patureau FW, Kuil M, Sandee AJ, Reek JNH (2008) Angew Chem Int Ed 47:3180
Breuil P-AR, Reek JNH (2009) Eur J Org Chem 6225
Breuil P-AR, Patureau FW, Reek JNH (2009) Angew Chem Int Ed 48:2162
Meeuwissen J, Kuil M, van der Burg AM, Sandee AJ, Reek JNH (2009) Chem Eur J 15:10272
Terrade FG, Kluwer AM, Detz RJ, Abiri Z, van der Burg AM, Reek JNH (2015) ChemCatChem 7:3368
Wieland J, Breit B (2010) Nat Chem 2:832
Pignataro L, Lynikaite B, Cvengroš J, Marchini M, Piarulli U, Gennari C (2009) Eur J Org Chem 2539
Pignataro L, Carboni S, Civera M, Colombo R, Piarulli U, Gennari C (2010) Angew Chem Int Ed 49:6633
Pignataro L, Boghi M, Civera M, Carboni S, Piarulli U, Gennari C (2012) Chem Eur J 18:1383
Pignataro L, Bovio C, Civera M, Carboni S, Piarulli U, Gennari C (2012) Chem Eur J 18:10368
Hattori G, Hori T, Miyake Y, Nishibayashi Y (2007) J Am Chem Soc 129:12930
Li Y, Feng Y, He YM, Chen F, Pan J, Fan Q-H (2008) Tetrahedron Lett 49:2878
Raynal M, Portier F, van Leeuwen PWHM, Bouteiller L (2013) J Am Chem Soc 135:17687
Thacker NC, Moteki SA, Takacs JM (2012) ACS Catal 2:2743–2752
Boogers JAF, Felfer U, Kotthaus M, Lefort L, Steinbauer G, de Vries AHM, de Vries JG (2007) Org Proc Res Dev 11:585–591
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Cettolin, M., Puylaert, P., de Vries, J.G. (2017). Rhodium-Catalysed Hydrogenations Using Monodentate Ligands. In: Claver, C. (eds) Rhodium Catalysis. Topics in Organometallic Chemistry, vol 61. Springer, Cham. https://doi.org/10.1007/3418_2017_174
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