Towards the Development of Frustrated Lewis Pair (FLP) Catalyzed Hydrogenations of Tertiary and Secondary Carboxylic Amides

Laura Köring; Nikolai A. Sitte; Jan Paradies

doi:10.1055/a-1681-3972

Synthesis, Inhaltsverzeichnis

Synthesis 2022; 54(05): 1287-1300
DOI: 10.1055/a-1681-3972

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Towards the Development of Frustrated Lewis Pair (FLP) Catalyzed Hydrogenations of Tertiary and Secondary Carboxylic Amides

Laura Köring

,

Nikolai A. Sitte

,

Jan Paradies ∗

Abstract

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Abstract

The development of the frustrated Lewis pair catalyzed hydrogenation of tertiary and secondary amides is reviewed. Detailed insight into our strategies in order to overcome challenges during the reaction development process is provided. Furthermore, the developed chemistry is extended to the hydrogenation of polyamides and of trifluoroacetamides for the convenient introduction of trifluoroethyl groups into organic molecules.

Key words

carboxylic amides - hydrogenation - imidoyl chlorides - frustrated Lewis pairs - tertiary amines - secondary amines

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References
1 Welch GC, Juan RR. S, Masuda JD, Stephan DW. Science 2006; 314: 1124
2 Ullrich M, Lough AJ, Stephan DW. J. Am. Chem. Soc. 2009; 131: 52
3 Chase PA, Jurca T, Stephan DW. Chem. Commun. 2008; 1701
4 Stephan DW, Erker G. Angew. Chem. Int. Ed. 2010; 49: 46
5 Stephan DW, Erker G. Angew. Chem. Int. Ed. 2015; 54: 6400
6 Stephan DW. J. Am. Chem. Soc. 2015; 137: 10018
7 Paradies J. Coord. Chem. Rev. 2019; 380: 170
8 Paradies J. Eur. J. Org. Chem. 2019; 283
9 Meng W, Feng X, Du H. Chin. J. Chem. 2020; 38: 625
10 Spies P, Erker G, Kehr G, Bergander K, Fröhlich R, Grimme S, Stephan DW. Chem. Commun. 2007; 5072
11 Lindqvist M, Borre K, Axenov K, Kótai B, Nieger M, Leskelä M, Pápai I, Repo T. J. Am. Chem. Soc. 2015; 137: 4038
12 Spies P, Schwendemann S, Lange S, Kehr G, Fröhlich R, Erker G. Angew. Chem. Int. Ed. 2008; 47: 7543
13 Chen D, Wang Y, Klankermayer J. Angew. Chem. Int. Ed. 2010; 49: 9475
14 Zhang Z, Du H. Angew. Chem. Int. Ed. 2015; 54: 623
15 Li S, Li G, Meng W, Du H. J. Am. Chem. Soc. 2016; 138: 12956
16 Greb L, Oña-Burgos P, Schirmer B, Grimme S, Stephan DW, Paradies J. Angew. Chem. Int. Ed. 2012; 51: 10164
17 Chernichenko K, Madarász Á, Pápai I, Nieger M, Leskelä M, Repo T. Nat. Chem. 2013; 5: 718
18 Wang Y, Chen W, Lu Z, Li ZH, Wang H. Angew. Chem. Int. Ed. 2013; 52: 7496
19 Mahdi T, Stephan DW. J. Am. Chem. Soc. 2014; 136: 15809
20 Scott DJ, Fuchter MJ, Ashley AE. J. Am. Chem. Soc. 2014; 136: 15813
21 Mahdi T, Stephan DW. Angew. Chem. Int. Ed. 2015; 54: 8511
22 Légaré M.-A, Courtemanche M.-A, Rochette É, Fontaine F.-G. Science 2015; 349: 513
23 Yin Q, Klare HF. T, Oestreich M. Angew. Chem. Int. Ed. 2017; 56: 3712
24 Basak S, Alvarez-Montoya A, Winfrey L, Melen RL, Morrill LC, Pulis AP. ACS Catal. 2020; 10: 4835
25 Wicker G, Schoch R, Paradies J. Org. Lett. 2021; 23: 3626
26 Basak S, Winfrey L, Kustiana BA, Melen RL, Morrill LC, Pulis AP. Chem. Soc. Rev. 2021; 50: 3720
27 Ma Y, Lou S.-J, Hou Z. Chem. Soc. Rev. 2021; 50: 1945
28 Maier AF. G, Tussing S, Schneider T, Flörke U, Qu Z.-W, Grimme S, Paradies J. Angew. Chem. Int. Ed. 2016; 55: 12219
29 Kojima M, Kanai M. Angew. Chem. Int. Ed. 2016; 55: 12224
30 Bader J, Maier AF. G, Paradies J, Hoge B. Eur. J. Inorg. Chem. 2017; 3053
31 Soltani Y, Dasgupta A, Gazis TA, Ould DM. C, Richards E, Slater B, Stefkova K, Vladimirov VY, Wilkins LC, Willcox D, Melen RL. Cell Rep. Phys. Sci. 2020; 1: 100016
32 Dasgupta A, Stefkova K, Babaahmadi R, Yates BF, Buurma NJ, Ariafard A, Richards E, Melen RL. J. Am. Chem. Soc. 2021; 143: 4451
33 Paradies J. Synlett 2013; 24: 777
34 Paradies J. Angew. Chem. Int. Ed. 2014; 53: 3552
35 Lam J, Szkop KM, Mosaferi E, Stephan DW. Chem. Soc. Rev. 2019; 48: 3592
36 Fang H, Oestreich M. Chem. Sci. 2020; 11: 12604
37 Sitte NA, Bursch M, Grimme S, Paradies J. J. Am. Chem. Soc. 2019; 141: 159
38 Köring L, Sitte NA, Bursch M, Grimme S, Paradies J. Chem. Eur. J. 2021; 27: 14179
39 Chardon A, Mohy El Dine T, Legay R, De Paolis M, Rouden J, Blanchet J. Chem. Eur. J. 2017; 23: 2005
40 Chadwick RC, Kardelis V, Lim P, Adronov A. J. Org. Chem. 2014; 79: 7728
41 Huang P.-Q, Lang Q.-W, Wang Y.-R. J. Org. Chem. 2016; 81: 4235
42 Augurusa A, Mehta M, Perez M, Zhu J, Stephan DW. Chem. Commun. 2016; 52: 12195
43 Bosshard HH, Mory R, Schmid M, Zollinger H. Helv. Chim. Acta 1959; 42: 1653
44 Bosshard HH, Zollinger H. Helv. Chim. Acta 1959; 42: 1659
45 Eilingsfeld H, Seefelder M, Weidinger H. Chem. Ber. 1963; 96: 2671
46 Grdinić M, Hahn V. J. Org. Chem. 1965; 30: 2381
47 Massey AG, Park AJ. J. Organomet. Chem. 1964; 2: 245
48 Massey AG, Park AJ. J. Organomet. Chem. 1966; 5: 218
49 Chakraborty D, Rodriguez A, Chen EY.-X. Macromolecules 2003; 36: 5470
50 Nicasio JA, Steinberg S, Inés B, Alcarazo M. Chem. Eur. J. 2013; 19: 11016
51 Naumann D, Butler H, Gnann R. Z. Anorg. Allg. Chem. 1992; 618: 74
52 Greb L, Daniliuc C.-G, Bergander K, Paradies J. Angew. Chem. Int. Ed. 2013; 52: 5876
53 Ullrich M, Lough AJ, Stephan DW. Organometallics 2010; 29: 3647
54 Böhrer H, Trapp N, Himmel D, Schleep M, Krossing I. Dalton Trans. 2015; 44: 7489
55 Mayer U, Gutmann V, Gerger W. Monatsh. Chem. 1975; 106: 1235
56 Gutmann V. Coord. Chem. Rev. 1976; 18: 225
57 Beckett MA, Strickland GC, Holland JR, Sukumar Varma K. Polymer 1996; 37: 4629
58 Beckett MA, Brassington DS, Coles SJ, Hursthouse MB. Inorg. Chem. Commun. 2000; 3: 530
59 Morgan MM, Marwitz AJ. V, Piers WE, Parvez M. Organometallics 2013; 32: 317
60 Hermanek S. Chem. Rev. 1992; 92: 325
61 Wrackmeyer B. Z. Naturforsch., B 2015; 70: 421
62 Lindqvist M, Sarnela N, Sumerin V, Chernichenko K, Leskelä M, Repo T. Dalton Trans. 2012; 41: 4310
63 Longobardi LE, Tang C, Stephan DW. Dalton Trans. 2014; 43: 15723
64 v. Braun J. Ber. Dtsch. Chem. Ges. 1904; 37: 3210
65 Greb L, Tussing S, Schirmer B, Oña-Burgos P, Kaupmees K, Lõkov M, Leito I, Grimme S, Paradies J. Chem. Sci. 2013; 4: 2788
66 Tussing S, Greb L, Tamke S, Schirmer B, Muhle-Goll C, Luy B, Paradies J. Chem. Eur. J. 2015; 21: 8056
67 Tussing S, Kaupmees K, Paradies J. Chem. Eur. J. 2016; 22: 7422
68 Chen D, Klankermayer J. Chem. Commun. 2008; 2130
69 Zhang Z, Du H. Org. Lett. 2015; 17: 6266
70 Kramer DL, Miller JT, Bergeron RJ, Khomutov R, Khomutov A, Porter CW. J. Cell. Physiol. 1993; 155: 399
71 Kaur N, Delcros J.-G, Archer J, Weagraff NZ, Martin B, Phanstiel OIV. J. Med. Chem. 2008; 51: 2551
72 Tsen C, Iltis M, Kaur N, Bayer C, Delcros J.-G, von Kalm L, Phanstiel OIV. J. Med. Chem. 2008; 51: 324
73 Kumar A, Yellepeddi VK, Vangara KK, Strychar KB, Palakurthi S. J. Drug Targeting 2011; 19: 770
74 Hayes CS, Shicora AC, Keough MP, Snook AE, Burns MR, Gilmour SK. Cancer Immunol. Res. 2014; 2: 274
75 Razvi SS, Choudhry H, Moselhy SS, Kumosani TA, Hasan MN, Zamzami MA, Abualnaja KO, Al-Malki AL, Alhosin M, Asami T. Biomed. Pharmacother. 2017; 93: 190
76 Peters MC, Minton A, Phanstiel OIV, Gilmour SK. Med. Sci. 2018; 6: 3
77 Khan A, Gamble LD, Upton DH, Ung C, Yu DM. T, Ehteda A, Pandher R, Mayoh C, Hébert S, Jabado N, Kleinman CL, Burns MR, Norris MD, Haber M, Tsoli M, Ziegler DS. Nat. Commun. 2021; 12: 971
78 Curran WV, Angier RB. J. Org. Chem. 1966; 31: 3867
79 Andrews KG, Faizova R, Denton RM. Nat. Commun. 2017; 8: 15913

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