Continuous Flow Organophosphorus Chemistry

Morodo Martinez, Romain; Bianchi, Pauline; Monbaliu, Jean-Christophe

doi:10.1002/ejoc.202000430

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Continuous Flow Organophosphorus Chemistry

Morodo Martinez, Romain; Bianchi, Pauline; Monbaliu, Jean-Christophe

2020 • In European Journal of Organic Chemistry, 33, p. 5236-5277

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https://hdl.handle.net/2268/249394

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10.1002/ejoc.202000430

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Keywords :

Flow chemistry; organophosphorus compounds

Abstract :

[en] With applications ranging from common laboratory reagents to agrochemical blockbusters, organophosphorus compounds are central to organic chemistry. Flow chemistry and related technologies have opened new perspectives in the many areas of organic chemistry, from methodology to total synthesis in R&D and production, regardless of the final potential industrial application. This review gives an overview of the most recent and significant advances in continuous flow organophosphorus chemistry.

Research center :

MolSys - Molecular Systems - ULiège [BE]

Disciplines :

Chemistry

Author, co-author :

Morodo Martinez, Romain ; Université de Liège - ULiège > Département de chimie (sciences) > Synthèse organique appliquée

Bianchi, Pauline ; Université de Liège - ULiège > Master en sc. chimiques, à fin.

Monbaliu, Jean-Christophe ; Université de Liège - ULiège > Département de chimie (sciences) > Synthèse organique appliquée

Language :

English

Title :

Continuous Flow Organophosphorus Chemistry

Publication date :

2020

Journal title :

European Journal of Organic Chemistry

ISSN :

1434-193X

eISSN :

1099-0690

Publisher :

John Wiley & Sons, United Kingdom

Volume :

Pages :

5236-5277

Peer reviewed :

Peer Reviewed verified by ORBi

Additional URL :

https://doi.org/10.1002/ejoc.202000430

Available on ORBi :

since 08 July 2020

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Bibliography

M. E. Weeks, J. Chem. Educ, 1932, 9, 11.
R. Jagnaux, in: Phosphore, in Histoire de la Chimie, Librairie Polytechnique, Paris, 1891, pp. 634–640.
A. Pfitzner, M. F. Bräu, J. Zweck, G. Brunklaus and H. Eckert, Angew. Chem. Int. Ed, 2004, 43, 4228–4231;
Angew. Chem, 2004, 116, 4324.
H. Diskowski and T. Hofmann, in: Phosphorus.
E. Desmidt, K. Ghyselbrecht, Y. Zhang, L. Pinoy, B. Van der Bruggen, W. Verstraete, K. Rabaey and B. Meesschaert, Crit. Rev. Environ. Sci. Technol, 2015, 45, 336–384.
D. Cordell, J.-O. Drangert and S. White, Glob. Environ. Chang, 2009, 19, 292–305.
D. Cordell and S. White, Sustainability, 2011, 3, 2027–2049.
J. Elser and E. Bennett, Nature, 2011, 478, 29–31.
Organisation for the Prohibition of Chemical Weapons, Chemical Weapons Convention, 2005, https://www.opcw.org/chemical-weapons-convention/download-convention (Accessed Mar 27, 2020).
D. Alexander, U. S. sanctions North Korea for killing of leader's half-brother with VX chemical, 2018, https://www.reuters.com/article/us-northkorea-malaysia-kim-usa/u-s-imposes-sanctions-on-pyongyang-over-slaying-of-north-korean-leaders-half-brother-idUSKCN1GJ031 (Accessed Mar 27, 2020).
C. C. T. Franca, A. S. D. Kitagawa, F. de A. S. Cavalcante, A. V. J. da Silva, E. Nepovimova and K. Kuca, Int. J. Mol. Sci, 2019, 20, 1222.
L. Howes, Novichok nerve agents may be added to Chemical Weapons Convention, 2019, https://cen.acs.org/policy/chemical-weapons/Novichok-nerve-agents-added-Chemical/97/i3 (Accessed Mar 27, 2020).
M. Peplow, Assassination attempt of Russian spy sparks chemical forensics investigation, 2018, https://cen.acs.org/articles/96/web/2018/03/Assassination-attempt-Russian-spy-sparks-chemical-forensics-investigation.html (Accessed Mar 27, 2020).
M. Peplow, Nerve agent attack on spy used “Novichok” poison, 2018, https://cen.acs.org/articles/96/i12/Nerve-agent-attack-on-spy-used-Novichok-poison.html (Accessed Mar 27, 2020).
Organisation for the Prohibition of Chemical Weapons, Incident in Salisbury, 2018, https://www.opcw.org/media-centre/featured-topics/incident-salisbury (Accessed Mar 27, 2020).
G. Bettermann, W. Krause, G. Riess and T. Hofmann, in: Phosphorus Compounds, Inorganic.
K. Schrödter, G. Bettermann, T. Staffel, F. Wahl, T. Klein and T. Hofmann, in: Phosphoric Acid and Phosphates.
J. Svara, N. Weferling, T. Hofmann, Phosphorus Compounds, in: Organic in Ullmann's Encycl. Ind. Chem.
M. B. Plutschack, B. Pieber, K. Gilmore and P. H. Seeberger, Chem. Rev, 2017, 117, 11796–11893.
L. Rogers and K. F. Jensen, Green Chem, 2019, 21, 3481–3498.
J. Britton and C. L. Raston, Chem. Soc. Rev, 2017, 46, 1250–1271.
M. Movsisyan, E. I. P. Delbeke, J. K. E. T. Berton, C. Battilocchio, S. V. Ley and C. V. Stevens, Chem. Soc. Rev, 2016, 45, 4892–4928.
M. A. Bezerra, V. A. Lemos, D. M. de Oliveira, C. G. Novaes, J. A. Barreto, J. P. S. Alves, U. M. F. da M. Cerqueira, Q. O. dos Santos and S. A. Araújo, Microchem. J, 2020, 155, 104731.
V. Sans and L. Cronin, Chem. Soc. Rev, 2016, 45, 2032–2043.
C. Mateos, M. J. Nieves-Remacha and J. A. Rincón, React. Chem. Eng, 2019, 4, 1536–1544.
R. Gérardy, N. Emmanuel, T. Toupy, V.-E. Kassin, N. N. Tshibalonza, M. Schmitz and J.-C. M. Monbaliu, Eur. J. Org. Chem, 2018, 2301–2351.
M. Di Filippo, C. Bracken and M. Baumann, Molecules, 2020, 25, 356.
D. L. Hughes, Org. Process Res. Dev, 2018, 22, 13–20.
D. Cambié, C. Bottecchia, N. J. W. Straathof, V. Hessel and T. Noël, Chem. Rev, 2016, 116, 10276–10341.
J. Sui, J. Yan, D. Liu, K. Wang and G. Luo, Small, 2019, 1902828.
S. Kubendhiran, Z. Bao, K. Dave and R.-S. Liu, ACS Appl. Nano Mater, 2019, 2, 1773–1790.
A. Hommes, H. J. Heeres and J. Yue, ChemCatChem, 2019, 11, 4671–4708.
R. Gérardy, R. Morodo, J. Estager, P. Luis, D. P. Debecker and J.-C. M. Monbaliu, Top. Curr. Chem, 2019, 377, 1.
T. H. Rehm, ChemPhotoChem 2020, 4, 235-254.
M. Atobe, H. Tateno and Y. Matsumura, Chem. Rev, 2018, 118, 4541–4572.
D. Pletcher, R. A. Green and R. C. D. Brown, Chem. Rev, 2018, 118, 4573–4591.
E. Bálint, Á. Tajti and G. Keglevich, Materials, 2019, 12, 788.
P. Jansa, O. Baszczyňski, E. Procházková, M. Dračínský and Z. Janeba, Green Chem, 2012, 14, 2282–2288.
E. Bálint, Á. Tajti, N. Tóth and G. Keglevich, Molecules, 2018, 23, 1618.
N. Tóth, Á. Tajti, K. Ladányi-Pára, E. Bálint and G. Keglevich, Phosphorus Sulfur Silicon Relat. Elem, 2019, 194, 285–286.
J. Britton, S. Majumdar and G. A. Weiss, Chem. Soc. Rev, 2018, 47, 5891–5918.
L. Tamborini, P. Fernandes, F. Paradisi and F. Molinari, Trends Biotechnol, 2018, 36, 73–88.
M. P. Thompson, I. Peñafiel, S. C. Cosgrove and N. J. Turner, Org. Process Res. Dev, 2019, 23, 9–18.
Y. Zhu, Q. Chen, L. Shao, Y. Jia and X. Zhang, React. Chem. Eng, 2020, 5, 9–32.
L. Babich, A. F. Hartog, M. A. van der Horst and R. Wever, Chem. Eur. J, 2012, 18, 6604–6609.
L. Babich, A. F. Hartog, L. J. C. van Hemert, F. P. J. T. Rutjes and R. Wever, ChemSusChem, 2012, 5, 2348–2353.
G. Tasnádi, M. Lukesch, M. Zechner, W. Jud, M. Hall, K. Ditrich, K. Baldenius, A. F. Hartog, R. Wever and K. Faber, Eur. J. Org. Chem, 2016, 45–50.
G. Tasnádi, M. Hall, K. Baldenius, K. Ditrich and K. Faber, J. Biotechnol, 2016, 233, 219–227.
F. Nagy, G. Tasnádi, D. Balogh-Weiser, E. Bell, M. Hall, K. Faber and L. Poppe, ChemCatChem, 2018, 10, 3490–3499.
D. Valikhani, J. M. Bolivar, M. Pfeiffer and B. Nidetzky, ChemCatChem, 2017, 9, 161–166.
D. Valikhani, J. M. Bolivar, M. Viefhues, D. N. McIlroy, E. X. Vrouwe and B. Nidetzky, ACS Appl. Mater. Interfaces, 2017, 9, 34641–34649.
Z. Liu, J. Zhang, X. Chen and P. G. Wang, ChemBioChem, 2002, 3, 348–355.
R. Heinzler, T. Fischöder, L. Elling and M. Franzreb, Adv. Synth. Catal, 2019, 361, 4506–4516.
J. Yin, T. Xu, N. Zhang and H. Wang, Anal. Chem, 2016, 88, 7730–7737.
J. Yin, S. Chen, N. Zhang and H. Wang, ACS Appl. Mater. Interfaces, 2018, 10, 21883–21890.
E. Calleri, G. Cattaneo, M. Rabuffetti, I. Serra, T. Bavaro, G. Massolini, G. Speranza and D. Ubiali, Adv. Synth. Catal, 2015, 357, 2520–2528.
G. Cattaneo, M. Rabuffetti, G. Speranza, T. Kupfer, B. Peters, G. Massolini, D. Ubiali and E. Calleri, ChemCatChem, 2017, 9, 4614–4620.
J. Britton, R. P. Dyer, S. Majumdar, C. L. Raston and G. A. Weiss, Angew. Chem. Int. Ed, 2017, 56, 2296–2301;
Angew. Chem, 2017, 129, 2336.
C. Zhu, C. Tang, Z. Cao, W. He, Y. Chen, X. Chen, K. Guo and H. Ying, Org. Process Res. Dev, 2014, 18, 1575–1581.
H. Huang, J. Ash and J. Y. Kang, Org. Lett, 2018, 20, 4938–4941.
H. Huang, J. Denne, C.-H. Yang, H. Wang and J. Y. Kang, Angew. Chem. Int. Ed, 2018, 57, 6624–6628;
Angew. Chem, 2018, 130, 6734.
J. Ash, H. Huang and J. Y. Kang, Org. Biomol. Chem, 2019, 17, 3812–3818.
P. Jansa, A. Holý, M. Dračinský, O. Baszczyňski, M. Česnek and Z. Janeba, Green Chem, 2011, 13, 882–888.
P. Jansa, A. Holy and M. Cesnek, Method of the Synthesis of Dialkyl Haloalkylphosphonates and Dialkyl Haloalkyloxyalkylphosphonates, 2012, WO 2012/013168 A1.
A. Jasiak, G. Mielniczak, K. Owsianik, M. Koprowski, D. Krasowska and J. Drabowicz, J. Org. Chem, 2019, 84, 2619–2625.
M. Baumann and I. R. Baxendale, J. Org. Chem, 2015, 80, 10806–10816.
B. T. Ramanjaneyulu, S. Vidyacharan, S. J. Yim and D.-P. Kim, Eur. J. Org. Chem, 2019, 7730–7734.
S. J. Yim, B. T. Ramanjaneyulu, S. Vidyacharan, Y. D. Yang, I. S. Kang and D.-P. Kim, Lab. Chip, 2020, 20, 973–978.
T. Angelini, S. Bonollo, D. Lanari, F. Pizzo and L. Vaccaro, Org. Biomol. Chem, 2013, 11, 5042–5046.
R. A. Sheldon, Green Chem, 2007, 9, 1273–1283.
E. Van Meenen, K. Moonen, D. Acke and C. V. Stevens, ARKIVOC, 2006, 31–45.
J. Britton, J. W. Castle, G. A. Weiss and C. L. Raston, Chem. Eur. J, 2016, 22, 10773–10776.
E. Bálint, Á. Tajti, K. Ladányi-Pára, N. Tóth, B. Mátravölgyi and G. Keglevich, Pure Appl. Chem, 2019, 91, 67–76.
B. J. Deadman, S. G. Collins and A. R. Maguire, Chem. Eur. J, 2015, 21, 2298–2308.
S. T. R. Müller, A. Murat, D. Maillos, P. Lesimple, P. Hellier and T. Wirth, Chem. Eur. J, 2015, 21, 7016–7020.
L. Di Marco, M. Hans, L. Delaude and J.-C. M. Monbaliu, Chem. Eur. J, 2016, 22, 4508–4514.
R. Gérardy, M. Winter, A. Vizza and J.-C. M. Monbaliu, React. Chem. Eng, 2017, 2, 149–158.
C. Empel and R. M. Koenigs, J. Flow Chem, 2020, 10, 157–160.
H. E. Bartrum, D. C. Blakemore, C. J. Moody and C. J. Hayes, Tetrahedron, 2013, 69, 2276–2282.
H. E. Bartrum, D. C. Blakemore, C. J. Moody and C. J. Hayes, Chem. Eur. J, 2011, 17, 9586–9589.
M. Roseau, N. Dhaouadi, C. Rolando, L. Chausset-Boissarie and M. Penhoat, J. Flow Chem, 2020, 10, 347–352.
C. G. Thomson, C. M. S. Jones, G. Rosair, D. Ellis, J. Marques-Hueso, A.-L. Lee and F. Vilela, J. Flow Chem, 2020, 10, 327–345.
T. Noël, Y. Cao and G. Laudadio, Acc. Chem. Res, 2019, 52, 2858–2869.
Y. Cao, B. Adriaenssens, A. de A. Bartolomeu, G. Laudadio, K. T. de Oliveira and T. Noël, J. Flow Chem, 2020, 10, 191–197.
S. Fransen, S. Ballet, J. Fransaer and S. Kuhn, J. Flow Chem, 2020, 10, 307–325.
M. Rueping, C. Vila and T. Bootwicha, ACS Catal, 2013, 3, 1676–1680.
F. Gelat, M. Roger, C. Penverne, A. Mazzad, C. Rolando and L. Chausset-Boissarie, RSC Adv, 2018, 8, 8385–8392.
Y. Li, Q. Yang, L. Yang, N. Lei and K. Zheng, Chem. Commun, 2019, 55, 4981–4984.
J.-C. M. R. Monbaliu, A. Cukalovic, J. Marchand-Brynaert and C. V. Stevens, Tetrahedron Lett, 2010, 51, 5830–5833.
J.-C. Monbaliu and J. Marchand-Brynaert, Tetrahedron Lett, 2008, 49, 1839–1842.
J.-C. Monbaliu, B. Tinant and J. Marchand-Brynaert, J. Org. Chem, 2010, 75, 5478–5486.
B. Schaefer and W. Siegel, Isomerization of Olefinic Compounds, 2014, US 2014/0051889 A1.
Y. Nishiyama, Y. Hazama, S. Yoshida and T. Hosoya, Org. Lett, 2017, 19, 3899–3902.
S. Manabe, C. M. Wong and C. S. Sevov, J. Am. Chem. Soc, 2020, 142, 3024–3031.
D. H. A. Rocha, D. C. G. A. Pinto and A. M. S. Silva, Eur. J. Org. Chem, 2018, 2443–2457.
V. Skelton, G. M. Greenway, S. J. Haswell, P. Styring, D. O. Morgan, B. Warrington and S. Y. F. Wong, Analyst, 2001, 126, 7–10.
V. Skelton, G. M. Greenway, S. J. Haswell, P. Styring, D. O. Morgan, B. H. Warrington and S. Y. F. Wong, Analyst, 2001, 126, 11–13.
E. Comer and M. G. Organ, J. Am. Chem. Soc, 2005, 127, 8160–8167.
D. Fernandez Rivas and S. Kuhn, Top. Curr. Chem, 2016, 374, 70.
Z. Dong, C. Delacour, K. Mc Carogher, P. A. Udepurkar and S. Kuhn, Materials, 2020, 13, 344.
M. Riccaboni, E. La Porta, A. Martorana and R. Attanasio, Tetrahedron, 2010, 66, 4032–4039.
E. Šinkovec and M. Krajnc, Org. Process Res. Dev, 2011, 15, 817–823.
M. Viviano, T. N. Glasnov, B. Reichart, G. Tekautz and C. O. Kappe, Org. Process Res. Dev, 2011, 15, 858–870.
H. Okamoto, H. Takahashi, T. Takane, Y. Nishiyama, K. Kakiuchi, S. Gohda and M. Yamaji, Synthesis, 2017, 49, 2949–2957.
S. Newton, C. F. Carter, C. M. Pearson, L. de C. Alves, H. Lange, P. Thansandote and S. V. Ley, Angew. Chem. Int. Ed, 2014, 53, 4915–4920;
Angew. Chem, 2014, 126, 5015.
K. A. Roper, M. B. Berry and S. V. Ley, Beilstein J. Org. Chem, 2013, 9, 1781–1790.
P. Llanes, C. Rodríguez-Escrich, S. Sayalero and M. A. Pericàs, Org. Lett, 2016, 18, 6292–6295.
I. R. Baxendale, J. Deeley, C. M. Griffiths-Jones, S. V. Ley, S. Saaby and G. K. Tranmer, Chem. Commun, 2006, 2566–2568.
C. D. Smith, I. R. Baxendale, G. K. Tranmer, M. Baumann, S. C. Smith, R. A. Lewthwaite and S. V. Ley, Org. Biomol. Chem, 2007, 5, 1562–1568.
C. J. Smith, C. D. Smith, N. Nikbin, S. V. Ley and I. R. Baxendale, Org. Biomol. Chem, 2011, 9, 1927–1937.
K. Donnelly, H. Zhang and M. Baumann, Molecules, 2019, 24, 3658.
V. Pace, P. Hoyos, L. Castoldi, P. Domínguez de María and A. R. Alcántara, ChemSusChem, 2012, 5, 1369–1379.
M. Tissot, J. Jacq and P. Pasau, Org. Process Res. Dev, 2020, 24, 802–806.
K. A. Roper, H. Lange, A. Polyzos, M. B. Berry, I. R. Baxendale and S. V. Ley, Beilstein J. Org. Chem, 2011, 7, 1648–1655.
D. E. Fitzpatrick, C. Battilocchio and S. V. Ley, Org. Process Res. Dev, 2016, 20, 386–394.
T. Y. S. But and P. H. Toy, Chem. Asian J, 2007, 2, 1340–1355.
R. H. Beddoe, K. G. Andrews, V. Magné, J. D. Cuthbertson, J. Saska, A. L. Shannon-Little, S. E. Shanahan, H. F. Sneddon and R. M. Denton, Science, 2019, 365, 910–914.
A. Manvar and A. Shah, Org. Biomol. Chem, 2014, 12, 8112–8124.
B. Ahmed-Omer and A. J. Sanderson, Org. Biomol. Chem, 2011, 9, 3854–3862.
World Health Organization, WHO Model Lists of Essential Medicines, 2019, https://www.who.int/medicines/publications/essentialmedicines/en/ (Accessed Mar 27, 2020).
A. Adamo, R. L. Beingessner, M. Behnam, J. Chen, T. F. Jamison, K. F. Jensen, J.-C. M. Monbaliu, A. S. Myerson, E. M. Revalor, D. R. Snead, et al., Science, 2016, 352, 61–67.
N. Ollivier, T. Toupy, R. C. Hartkoorn, R. Desmet, J.-C. M. Monbaliu and O. Melnyk, Nat. Commun, 2018, 9, 2847.
V. Agouridas, O. El Mahdi, V. Diemer, M. Cargoët, J.-C. M. Monbaliu and O. Melnyk, Chem. Rev, 2019, 119, 7328–7443.
Y. Yang, Y. Cui, K. Sang, Y. Dong, Z. Ni, S. Ma and H. Hu, Nature, 2018, 554, 317–322.
V.-E. H. Kassin, R. Gérardy, T. Toupy, D. Collin, E. Salvadeo, F. Toussaint, K. Van Hecke and J.-C. M. Monbaliu, Green Chem, 2019, 21, 2952–2966.
V.-E. H. Kassin, T. Toupy, G. Petit, P. Bianchi, E. Salvadeo and J.-C. M. Monbaliu, J. Flow Chem, 2020, 10, 167–179.
J. A. Bisceglia and L. R. Orelli, Curr. Org. Chem, 2015, 19, 744–775.
N. Miyake and T. Kitazume, J. Fluorine Chem, 2003, 122, 243–246.
D. A. Snyder, C. Noti, P. H. Seeberger, F. Schael, T. Bieber, G. Rimmel and W. Ehrfeld, Helv. Chim. Acta, 2005, 88, 1–9.
L. F. Tietze and D. Liu, ARKIVOC, 2008, 193.
D. Webb and T. F. Jamison, Org. Lett, 2012, 14, 568–571.
D. Webb and T. F. Jamison, Org. Lett, 2012, 14, 2465–2467.
D. Ghislieri, K. Gilmore and P. H. Seeberger, Angew. Chem. Int. Ed, 2015, 54, 678–682;
Angew. Chem, 2015, 127, 688.
T. Doi, H. Otaka, K. Umeda and M. Yoshida, Tetrahedron, 2015, 71, 6463–6470.
S. Ogasawara and Y. Hayashi, Synthesis, 2016, 48, 424–428.
Z. Zhang, Z. Bao and H. Xing, Org. Biomol. Chem, 2014, 12, 3151–3162.
A.-C. Bédard, A. Adamo, K. C. Aroh, M. G. Russell, A. A. Bedermann, J. Torosian, B. Yue, K. F. Jensen and T. F. Jamison, Science, 2018, 361, 1220–1225.
M. Marinozzi, F. Pertusati and M. Serpi, Chem. Rev, 2016, 116, 13991–14055.
J. C. Gilbert and U. Weerasooriya, J. Org. Chem, 1982, 47, 1837–1845.
S. Müller, B. Liepold, G. J. Roth and H. J. Bestmann, Synlett, 1996, 521–522.
G. J. Roth, B. Liepold, S. G. Müller and H. J. Bestmann, Synthesis, 2004, 59–62.
I. R. Baxendale, S. V. Ley, A. C. Mansfield and C. D. Smith, Angew. Chem. Int. Ed, 2009, 48, 4017–4021;
Angew. Chem, 2009, 121, 4077.
D. Parmar, E. Sugiono, S. Raja and M. Rueping, Chem. Rev, 2014, 114, 9047–9153.
S. Fritzsche, S. Ohla, P. Glaser, D. S. Giera, M. Sickert, C. Schneider and D. Belder, Angew. Chem. Int. Ed, 2011, 50, 9467–9470;
Angew. Chem, 2011, 123, 9639.
M. Rueping, T. Bootwicha and E. Sugiono, Beilstein J. Org. Chem, 2012, 8, 300–307.
H.-H. Liao, C.-C. Hsiao, E. Sugiono and M. Rueping, Chem. Commun, 2013, 49, 7953.
E. Sugiono and M. Rueping, Beilstein J. Org. Chem, 2013, 9, 2457–2462.
T. Yasukawa, R. Masuda and S. Kobayashi, Nat. Catal, 2019, 2, 1088–1092.
M. Colella, C. Carlucci and R. Luisi, Top. Curr. Chem, 2018, 376, 46.
G. Strappaveccia, D. Lanari, D. Gelman, F. Pizzo, O. Rosati, M. Curini and L. Vaccaro, Green Chem, 2013, 15, 199–204.
G. Strappaveccia, T. Angelini, L. Bianchi, S. Santoro, O. Piermatti, D. Lanari and L. Vaccaro, Adv. Synth. Catal, 2016, 358, 2134–2139.
S. Ceylan, H. Law, A. Kirschning and P. Toy, Synthesis, 2016, 48, 145–150.
U. P. N. Tran, K. J. Hock, C. P. Gordon, R. M. Koenigs and T. V. Nguyen, Chem. Commun, 2017, 53, 4950–4953.
P. Ranjan, G. M. Ojeda, U. K. Sharma and E. V. Van der Eycken, Chem. Eur. J, 2019, 25, 2442–2446.
L. Osorio-Planes, C. Rodríguez-Escrich and M. A. Pericàs, Chem. Eur. J, 2014, 20, 2367–2372.
L. Clot-Almenara, C. Rodríguez-Escrich, L. Osorio-Planes and M. A. Pericàs, ACS Catal, 2016, 6, 7647–7651.
G. Xu, J. Cao, Y. Zhao, L. Zheng, M. Tao and W. Zhang, Chem. Asian J, 2017, 12, 2565–2575.
Phosphazenes, in IUPAC Compend. Chem. Terminol., Blackwell Scientific Publications, Oxford, 1997.
Y. Kondo, in: Superbases Org. Synth (Ed.: T. Ishikawa), John Wiley & Sons, Ltd, Chichester, UK, 2009, pp. 145–185.
M. Baumann, I. R. Baxendale, S. V. Ley, C. D. Smith and G. K. Tranmer, Org. Lett, 2006, 8, 5231–5234.
C. F. Carter, H. Lange, S. V. Ley, I. R. Baxendale, B. Wittkamp, J. G. Goode and N. L. Gaunt, Org. Process Res. Dev, 2010, 14, 393–404.
I. R. Baxendale, S. V. Ley, C. D. Smith, L. Tamborini and A.-F. Voica, J. Comb. Chem, 2008, 10, 851–857.
M. Baumann, I. Baxendale, M. Brasholz, J. Hayward, S. Ley and N. Nikbin, Synlett, 2011, 1375–1380.
R. Ballini, L. Barboni, L. Castrica, F. Fringuelli, D. Lanari, F. Pizzo and L. Vaccaro, Adv. Synth. Catal, 2008, 350, 1218–1224.
A. Zvagulis, S. Bonollo, D. Lanari, F. Pizzo and L. Vaccaro, Adv. Synth. Catal, 2010, 352, 2489–2496.
S. Bonollo, D. Lanari, J. M. Longo and L. Vaccaro, Green Chem, 2012, 14, 164–169.
A. J. M. Farley, P. Jakubec, A. M. Goldys and D. J. Dixon, Tetrahedron, 2018, 74, 5206–5212.
Z. Wang, R. Gérardy, G. Gauron, C. Damblon and J.-C. M. Monbaliu, React. Chem. Eng, 2019, 4, 17–26.
B. Gutmann, D. Cantillo and C. O. Kappe, Angew. Chem. Int. Ed, 2015, 54, 6688–6728;
Angew. Chem, 2015, 127, 6788.
H. Liang, Synlett, 2008, 2554–2555.
F. J. Strauss, D. Cantillo, J. Guerra and C. O. Kappe, React. Chem. Eng, 2016, 1, 472–476.
G. Glotz, R. Lebl, D. Dallinger and C. O. Kappe, Angew. Chem. Int. Ed, 2017, 56, 13786–13789;
Angew. Chem, 2017, 129, 13974.
B. Gutmann and C. O. Kappe, J. Flow Chem, 2017, 7, 65–71.
A. Steiner, J. D. Williams, O. de Frutos, J. A. Rincón, C. Mateos and C. O. Kappe, Green Chem, 2020, 22, 448–454.
S. C. Born, C. E. R. Edwards, B. Martin and K. F. Jensen, Tetrahedron, 2018, 74, 3137–3142.
A. K. Ghosh, A. Sarkar and M. Brindisi, Org. Biomol. Chem, 2018, 16, 2006–2027.
M. Baumann, I. R. Baxendale, S. V. Ley, N. Nikbin, C. D. Smith and J. P. Tierney, Org. Biomol. Chem, 2008, 6, 1577–1586.
K. Huard, S. W. Bagley, E. Menhaji-Klotz, C. Préville, J. A. Southers, A. C. Smith, D. J. Edmonds, J. C. Lucas, M. F. Dunn, N. M. Allanson, et al., J. Org. Chem, 2012, 77, 10050–10057.
L. Guetzoyan, R. J. Ingham, N. Nikbin, J. Rossignol, M. Wolling, M. Baumert, N. A. Burgess-Brown, C. M. Strain-Damerell, L. Shrestha, P. E. Brennan, et al., Med. Chem. Commun, 2014, 5, 540–546.
P. Filipponi, C. Ostacolo, E. Novellino, R. Pellicciari and A. Gioiello, Org. Process Res. Dev, 2014, 18, 1345–1353.
M. A. Marsini, F. G. Buono, J. C. Lorenz, B.-S. Yang, J. T. Reeves, K. Sidhu, M. Sarvestani, Z. Tan, Y. Zhang, N. Li, et al., Green Chem, 2017, 19, 1454–1461.
C. R. Sagandira and P. Watts, Beilstein J. Org. Chem, 2019, 15, 2577–2589.
INCHEM, International Programme on Chemical Safety, http://www.inchem.org/#/search, (Accessed Mar 27, 2020).
Y. J. Jang, K. Kim, O. G. Tsay, D. A. Atwood and D. G. Churchill, Chem. Rev. 2015, 115, PR1–PR76.
B. Picard, I. Chataigner, J. Maddaluno and J. Legros, Org. Biomol. Chem, 2019, 17, 6528–6537.
A. A. Wang, W. Chen and A. Mulchandani, Biotechnol. Bioeng, 2005, 91, 379–386.
E. N. Efremenko, I. V. Lyagin, F. M. Plieva, I. Y. Galaev and B. Mattiasson, Appl. Biochem. Biotechnol, 2009, 159, 251–260.
M. Ben Brahim, R. Abdelhédi and Y. Samet, Desalin. Water Treat, 2014, 52, 6784–6791.
M. Sheydaei, M. Karimi and V. Vatanpour, J. Photochem. Photobiol. A, 2019, 384, 112068.
G. S. Cordeiro, R. S. Rocha, R. B. Valim, F. L. Migliorini, M. R. Baldan, M. R. V. Lanza and N. G. Ferreira, Diamond Relat. Mater, 2013, 32, 54–60.
M. M. Y. Motamedhashemi, F. Egolfopoulos and T. Tsotsis, J. Membr. Sci, 2011, 376, 119–131.
E. A. Kozlova, T. P. Lyubina, M. A. Nasalevich, A. V. Vorontsov, A. V. Miller, V. V. Kaichev and V. N. Parmon, Catal. Commun, 2011, 12, 597–601.
A. M. Plonka, Q. Wang, W. O. Gordon, A. Balboa, D. Troya, W. Guo, C. H. Sharp, S. D. Senanayake, J. R. Morris, C. L. Hill, et al., J. Am. Chem. Soc, 2017, 139, 599–602.