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CC BY 4.0 · SynOpen 2023; 07(01): 46-57
DOI: 10.1055/a-2005-5443
DOI: 10.1055/a-2005-5443
graphical review
Frustrated Lewis Pair Catalyzed Reactions
The Deutsche Forschungsgemeinschaft (DFG) (German Research Foundation) is gratefully acknowledged for financial support (PA1562/16-1; PA1562/18-1). R. Zhou is grateful to Paderborn University for a doctoral fellowship.
Abstract
In recent years, frustrated Lewis pairs have been widely used for the activation of small molecules and in catalytic transformations. This graphical review aims to provide a fundamental understanding of frustrated Lewis pair reactivity and the exploitation thereof in catalytic reactions.
Key words
frustrated Lewis pairs - boron - phosphine - nitrogen - hydrogenation - C–C bonds - C–N bondsPublikationsverlauf
Eingereicht: 14. Dezember 2022
Angenommen nach Revision: 02. Januar 2023
Accepted Manuscript online:
02. Januar 2023
Artikel online veröffentlicht:
01. Februar 2023
© 2023. The Author(s). This is an open access article published by Thieme under the terms of the Creative Commons Attribution License, permitting copying and reproduction so long as the original work is given appropriate credit. Contents may not be used for commercial purposes or adapted, remixed, transformed or built upon. (https://creativecommons.org/licenses/by/4.0/)
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References
- 1a Welch GC, San Juan RR, Masuda JD, Stephan DW. Science 2006; 314: 1121
- 1b Stephan DW. Org. Biomol. Chem. 2012; 10: 5740
- 1c Stephan DW. J. Am. Chem. Soc. 2015; 137: 10018
- 1d Stephan DW, Erker G. Chem. Sci. 2014; 5: 2625
- 1e Stephan DW, Erker G. Angew. Chem. Int. Ed. 2010; 49: 46
- 1f Paradies J. Synlett 2013; 24: 777
- 1g Paradies J. Angew. Chem. Int. Ed. 2014; 53: 3552
- 1h Stephan DW, Erker G. Angew. Chem. Int. Ed. 2015; 54: 6400
- 1i Lam J, Szkop KM, Mosaferi E, Stephan DW. Chem. Soc. Rev. 2019; 48: 3592
- 1j Stephan DW. J. Am. Chem. Soc. 2021; 143: 20002
- 1k Stephan DW. Chem 2020; 6: 1520
- 1l Lawson JR, Wilkins LC, Melen RL. Chem. Eur. J. 2017; 23: 10997
- 1m Carden JL, Dasgupta A, Melen RL. Chem. Soc. Rev. 2020; 49: 1706
- 1n Brown HC, Schlesinger HI, Cardon SZ. J. Am. Chem. Soc. 1942; 64: 325
- 1o Rocchigiani L, Ciancaleoni G, Zuccaccia C, Macchioni A. J. Am. Chem. Soc. 2014; 136: 112
- 1p Holtrop F, Jupp AR, van Leest NP, Paradiz Dominguez M, Williams RM, Brouwer AM, de Bruin B, Ehlers AW, Slootweg JC. Chem. Eur. J. 2020; 26: 9005
- 1q Greb L, Daniliuc C.-G, Bergander K, Paradies J. Angew. Chem. Int. Ed. 2013; 52: 5876
- 1r Tussing S, Greb L, Tamke S, Schirmer B, Muhle-Goll C, Luy B, Paradies J. Chem. Eur. J. 2015; 21: 8056
- 1s Chen D, Wang Y, Klankermayer J. Angew. Chem. 2010; 122: 9665
- 1t Greb L, Paradies J. Top. Curr. Chem. 2013; 334: 81
- 1u Köring L, Sitte NA, Bursch M, Grimme S, Paradies J. Chem. Eur. J. 2021; 27: 14179
- 1v Tu X.-S, Zeng N.-N, Li R.-Y, Zhao Y.-Q, Xie D.-Z, Peng Q, Wang X.-C. Angew. Chem. Int. Ed. 2018; 57: 15096
- 1w Lindqvist M, Borre K, Axenov K, Kótai B, Nieger M, Leskelä M, Pápai I, Repo T. J. Am. Chem. Soc. 2015; 137: 4038
- 1x Ullrich M, Lough AJ, Stephan DW. J. Am. Chem. Soc. 2009; 131: 52
- 1y Massey AG, Park AJ. J. Organomet. Chem. 1964; 2: 245
- 1z Liu Y, Du H. J. Am. Chem. Soc. 2013; 135: 6810
- 1aa Rokob TA, Hamza A, Stirling A, Soós T, Pápai I. Angew. Chem. Int. Ed. 2008; 47: 2435
- 1ab Grimme S, Kruse H, Goerigk L, Erker G. Angew. Chem. Int. Ed. 2010; 49: 1402
- 1ac Tussing S, Kaupmees K, Paradies J. Chem. Eur. J. 2016; 22: 7422
- 2a Welch GC, Stephan DW. J. Am. Chem. Soc. 2007; 129: 1880
- 2b Spies P, Schwendemann S, Lange S, Kehr G, Fröhlich R, Erker G. Angew. Chem. Int. Ed. 2008; 47: 7543
- 2c Geier SJ, Chase PA, Stephan DW. Chem. Commun. 2010; 46: 4884
- 2d Stephan DW, Greenberg S, Graham TW, Chase P, Hastie JJ, Geier SJ, Farrell JM, Brown CC, Heiden ZM, Welch GC, Ullrich M. Inorg. Chem. 2011; 50: 12338
- 2e Chase PA, Jurca T, Stephan DW. Chem. Commun. 2008; 1701
- 2f Scott DJ, Fuchter MJ, Ashley AE. J. Am. Chem. Soc. 2014; 136: 15813
- 2g Mahdi T, Stephan DW. J. Am. Chem. Soc. 2014; 136: 15809
- 2h Greb L, Oña-Burgos P, Schirmer B, Grimme S, Stephan DW, Paradies J. Angew. Chem. Int. Ed. 2012; 51: 10164
- 2i Mahaut D, Champagne B, Berionni G. ChemCatChem 2022; 14: e202200294
- 2j Eros G, Mehdi H, Pápai I, Rokob TA, Király P, Tárkányi G, Soós T. Angew. Chem. Int. Ed. 2010; 49: 6559
- 2k Reddy JS, Xu B.-H, Mahdi T, Fröhlich R, Kehr G, Stephan DW, Erker G. Organometallics 2012; 31: 5638
- 2l Nicasio JA, Steinberg S, Inés B, Alcarazo M. Chem. Eur. J. 2013; 19: 11016
- 2m Wölke C, Daniliuc CG, Kehr G, Erker G. J. Organomet. Chem. 2019; 899: 120879
- 2n Khan I, Manzotti M, Tizzard GJ, Coles SJ, Melen RL, Morrill LC. ACS Catal. 2017; 7: 7748
- 2o Chernichenko K, Madarász A, Pápai I, Nieger M, Leskelä M, Repo T. Nat. Chem. 2013; 5: 718
- 2p Wech F, Hasenbeck M, Gellrich U. Chem. Eur. J. 2020; 26: 13445
- 2q Wech F, Gellrich U. ACS Catal. 2022; 12: 5388
- 3a Chen D, Klankermayer J. Chem. Commun. 2008; 2130
- 3b Ghattas G, Chen D, Pan F, Klankermayer J. Dalton Trans. 2012; 41: 9026
- 3c Wang G, Chen C, Du T, Zhong W. Adv. Synth. Catal. 2014; 356: 1747
- 3d Hamza A, Sorochkina K, Kótai B, Chernichenko K, Berta D, Bolte M, Nieger M, Repo T, Pápai I. ACS Catal. 2020; 10: 14290
- 3e Wei S, Du H. J. Am. Chem. Soc. 2014; 136: 12261
- 3f Zhang Z, Du H. Angew. Chem. Int. Ed. 2015; 54: 623
- 3g Gao B, Feng X, Meng W, Du H. Angew. Chem. Int. Ed. 2020; 59: 4498
- 4a Millot N, Santini CC, Fenet B, Basset JM. Eur. J. Inorg. Chem. 2002; 3328
- 4b Farrell JM, Heiden ZM, Stephan DW. Organometallics 2011; 30: 4497
- 4c Chatterjee I, Oestreich M. Angew. Chem. Int. Ed. 2015; 54: 1965
- 4d Khan I, Reed-Berendt BG, Melen RL, Morrill LC. Angew. Chem. Int. Ed. 2018; 57: 12356
- 4e Li S, Li G, Meng W, Du H. J. Am. Chem. Soc. 2016; 138: 12956
- 4f Li S, Meng W, Du H. Org. Lett. 2017; 19: 2604
- 4g Zhao W, Feng X, Yang J, Du H. Tetrahedron Lett. 2019; 60: 1193
- 5a Chen C, Harhausen M, Liedtke R, Bussmann K, Fukazawa A, Yamaguchi S, Petersen JL, Daniliuc CG, Fröhlich R, Kehr G, Erker G. Angew. Chem. 2013; 125: 6108
- 5b Tamke S, Qu Z.-W, Sitte NA, Flörke U, Grimme S, Paradies J. Angew. Chem. Int. Ed. 2016; 55: 4336
- 5c Maier AF. G, Tussing S, Zhu H, Wicker G, Tzvetkova P, Flörke U, Daniliuc CG, Grimme S, Paradies J. Chem. Eur. J. 2018; 24: 16287
- 5d Chan JZ, Yao W, Hastings BT, Lok CK, Wasa M. Angew. Chem. 2016; 128: 14081
- 5e Wicker G, Zhou R, Schoch R, Paradies J. Angew. Chem. Int. Ed. 2022; 61: e202204378
- 5f Wicker G, Schoch R, Paradies J. Org. Lett. 2021; 23: 3626
- 5g Zhou R, Paradies J. Eur. J. Org. Chem. 2021; 6334
- 5h Chen G.-Q, Türkyilmaz F, Daniliuc CG, Bannwarth C, Grimme S, Kehr G, Erker G. Org. Biomol. Chem. 2015; 13: 10477
- 5i Hasenbeck M, Müller T, Gellrich U. Catal. Sci. Technol. 2019; 9: 2438
- 5j Li R, Chen Y, Jiang K, Wang F, Lu C, Nie J, Chen Z, Yang G, Chen Y.-C, Zhao Y, Ma C. Chem. Commun. 2019; 55: 1217
- 5k Dasgupta A, Stefkova K, Babaahmadi R, Yates BF, Buurma NJ, Ariafard A, Richards E, Melen RL. J. Am. Chem. Soc. 2021; 143: 4451
- 6a Mahdi T, Stephan DW. Angew. Chem. Int. Ed. 2013; 52: 12418
- 6b Mahdi T, Stephan DW. Chem. Eur. J. 2015; 21: 11134
- 6c Tussing S, Ohland M, Wicker G, Flörke U, Paradies J. Dalton Trans. 2017; 46: 1539
- 6d Guru MM, De S, Dutta S, Koley D, Maji B. Chem. Sci. 2019; 10: 7964
- 6e Fasano V, Ingleson MJ. Chem. Eur. J. 2017; 23: 2217
- 6f Pan Z, Shen L, Song D, Xie Z, Ling F, Zhong W. J. Org. Chem. 2018; 83: 11502
- 6g Dorkó É, Szabó M, Kótai B, Pápai I, Domján A, Soós T. Angew. Chem. Int. Ed. 2017; 56: 9512
- 6h Hoshimoto Y, Kinoshita T, Hazra S, Ohashi M, Ogoshi S. J. Am. Chem. Soc. 2018; 140: 7292
- 7a Caputo CB, Hounjet LJ, Dobrovetsky R, Stephan DW. Science 2013; 341: 1374
- 7b Brož B, Marek A. J. Labelled Compd. Radiopharm. 2019; 62: 743
- 7c Wang T, Xu M, Jupp AR, Chen S.-M, Qu Z.-W, Grimme S, Stephan DW. Chem. Commun. 2022; 58: 1175
- 7d Mandal D, Gupta R, Young RD. J. Am. Chem. Soc. 2018; 140: 10682
- 7e Caputo CB, Stephan DW. Organometallics 2012; 31: 27
- 8a Tan M, Zhang Y. Tetrahedron Lett. 2009; 50: 4912
- 8b Mahdi T, Stephan DW. Angew. Chem. Int. Ed. 2015; 54: 8511
- 8c Chatterjee I, Porwal D, Oestreich M. Angew. Chem. Int. Ed. 2017; 56: 3389
- 8d Saito K, Kondo K, Akiyama T. Org. Lett. 2015; 17: 3366
- 8e Maier AF. G, Tussing S, Schneider T, Flörke U, Qu Z.-W, Grimme S, Paradies J. Angew. Chem. Int. Ed. 2016; 55: 12219
- 8f Stepen AJ, Bursch M, Grimme S, Stephan DW, Paradies J. Angew. Chem. Int. Ed. 2018; 57: 15253
- 8g Sitte NA, Bursch M, Grimme S, Paradies J. J. Am. Chem. Soc. 2019; 141: 159
- 8h Köring L, Sitte NA, Paradies J. Synthesis 2022; 54: 1287
- 8i Fang H, Oestreich M. Angew. Chem. Int. Ed. 2020; 59: 11394
- 8j Peng Y, Oestreich M. Org. Lett. 2022; 24: 2940
- 9a Légaré M.-A, Courtemanche M.-A, Rochette É, Fontaine F.-G. Science 2015; 349: 513
- 9b Shang M, Wang X, Koo SM, Youn J, Chan JZ, Yao W, Hastings BT, Wasa M. J. Am. Chem. Soc. 2017; 139: 95
- 9c Chang Y, Yesilcimen A, Cao M, Zhang Y, Zhang B, Chan JZ, Wasa M. J. Am. Chem. Soc. 2019; 141: 14570
- 9d Légaré M.-A, Rochette É, Légaré Lavergne J, Bouchard N, Fontaine F.-G. Chem. Commun. 2016; 52: 5387
- 9e Chernichenko K, Lindqvist M, Kótai B, Nieger M, Sorochkina K, Pápai I, Repo T. J. Am. Chem. Soc. 2016; 138: 4860
- 9f Légaré Lavergne J, Jayaraman A, Misal Castro LC, Rochette É, Fontaine F.-G. J. Am. Chem. Soc. 2017; 139: 14714
- 9g Shang M, Chan JZ, Cao M, Chang Y, Wang Q, Cook B, Torker S, Wasa M. J. Am. Chem. Soc. 2018; 140: 10593
- 9h Zhang Q, Li Y, Zhang L, Luo S. Angew. Chem. Int. Ed. 2021; 60: 10971
- 10a Gyömöre Á, Bakos M, Földes T, Pápai I, Domján A, Soós T. ACS Catal. 2015; 5366
- 10b Scott DJ, Simmons TR, Lawrence EJ, Wildgoose GG, Fuchter MJ, Ashley AE. ACS Catal. 2015; 5: 5540
- 10c Ghattas G, Bizzarri C, Hölscher M, Langanke J, Gürtler C, Leitner W, Subhani MA. Chem. Commun. 2017; 53: 3205
- 10d Zhang H, Zhan X.-Y, Dong Y, Yang J, He S, Shi Z.-C, Zhang X.-M, Wang J.-Y. RSC Adv. 2020; 10: 16942