Iron Catalysis in Target Synthesis

Peter DaBell; Stephen P. Thomas

doi:10.1055/s-0039-1690813

Synthesis, Table of Contents

Synthesis 2020; 52(07): 949-963
DOI: 10.1055/s-0039-1690813

review

Iron Catalysis in Target Synthesis

Peter DaBell

,

Stephen P. Thomas ∗

School of Chemistry, University of Edinburgh, Joseph Black Building, Edinburgh, EH9 3FK, UK Email: stephen.thomas@ed.ac.uk

› Author Affiliations

Abstract

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Abstract

The use of iron-catalysed organic transformations in the total syntheses of natural products has increased significantly. Iron-catalysed cross-coupling reactions are now widely applied in total syntheses and many other transformations, such as alkene functionalisation, oxidation, and cyclisation. The development of these processes, as well as many examples of their use in target synthesis, is presented here.

1 Introduction

2 Cross-Coupling Reactions

3 Functionalisation of Unactivated Alkenes

4 Carbocyclisation Reactions

5 Oxidations

6 Further Examples

7 Conclusions

Key words

alkene functionalisation - carbocyclisation - cross-coupling - drug molecule synthesis - iron catalysis - natural product synthesis - oxidation - transition metal catalysis

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References

References
1 Bolm C, Legros J, Le Paih J, Zani L. Chem. Rev. 2004; 104: 6217
2 Bauer I, Knölker H.-J. Chem. Rev. 2015; 115: 3170
3 Iron Catalysis in Organic Chemistry: Reactions and Applications. Plietker B. Wiley-VCH; Weinheim: 2008
4 Plietker B, Dieskau A. Eur. J. Org. Chem. 2009; 775
5 Czaplik WM, Mayer M, Cvengroš J, Jacobi von Wangelin A. ChemSusChem 2009; 2: 396
6 Perutz MF. Ann. Rev. Biochem. 1979; 48: 327
7 Handbook on the Toxicology of Metals, 2nd ed. Friberg L, Nordberg GF, Vouk VB. Elsevier; Amsterdam: 1986
8 Ghosh M, Singh KK, Panda C, Weitz A, Hendrich MP, Collins TJ, Dhar BB, Sen Gupta S. J. Am. Chem. Soc. 2014; 136: 9524
9 Chen MS, White MC. Science 2007; 318: 783
10 Padron JI, Martin VS. Top. Organomet. Chem. 2011; 33: 1
11 Fürstner A, Martin R. Chem. Lett. 2005; 34: 624
12 Metal-Catalyzed Cross-Coupling Reactions, 2nd ed. de Meijere A, Diederich F. Wiley-VCH; Weinheim: 2004
13 Kharasch MS, Fields EK. J. Am. Chem. Soc. 1941; 63: 2316
14 Tamura M, Kochi JK. J. Am. Chem. Soc. 1971; 93: 1487
15 Tamao K, Sumitani K, Kumada M. J. Am. Chem. Soc. 1972; 94: 4374
16 Corriu RJ. P, Masse JP. J. Chem. Soc., Chem. Commun. 1972; 144
17 Cahiez G, Avedissian H. Synthesis 1998; 1199
18 Dohle W, Kopp F, Cahiez G, Knochel P. Synlett 2001; 1901
19 Camacho-Dávila AA. Synth. Commun. 2008; 38: 3823
20 Robinson JE, Taylor RJ. K. Chem. Commun. 2007; 1617
21 Gaukroger K, Hadfield JA, Hepworth LA, Lawrence NJ, McGown AT. J. Org. Chem. 2001; 66: 8135
22 Lawrence NJ, Muhammad F. Tetrahedron 1998; 54: 15345
23 Tewari N, Maheshwari N, Medhane R, Nizar H, Prasad M. Org. Process Res. Dev. 2012; 16: 1566
24 Fürstner A, Leitner A. Angew. Chem. Int. Ed. 2002; 41: 609
25 Scheiper B, Glorius F, Leitner A, Fürstner A. Proc. Natl. Acad. Sci. U.S.A. 2004; 101: 11960
26 Fürstner A, Leitner A, Méndez M, Krause H. J. Am. Chem. Soc. 2002; 124: 13856
27 Bogdanović B, Schwickardi M. Angew. Chem. Int. Ed. 2000; 39: 4610
28 Bedford RB, Bruce DW, Frost RM, Hird M. Chem. Commun. 2005; 4161
29 Bedford RB, Betham M, Bruce DW, Davis SA, Frost RM, Hird M. Chem. Commun. 2006; 1398
30 Nakamura M, Matsuo K, Ito S, Nakamura E. J. Am. Chem. Soc. 2004; 126: 3686
31 Bedford RB. Acc. Chem. Res. 2015; 48: 1485
32 Adams CJ, Bedford RB, Carter E, Gower NJ, Haddow MF, Harvey JN, Huwe M, Cartes M. Á, Mansell SM, Mendoza C, Murphy DM, Neeve EC, Nunn J. J. Am. Chem. Soc. 2012; 134: 10333
33 Bedford RB, Carter E, Cogswell PM, Gower NJ, Haddow MF, Harvey JN, Murphy DM, Neeve EC, Nunn J. Angew. Chem. Int. Ed. 2013; 52: 1285
34 Kleimark J, Hedström A, Larsson P.-F, Johansson C, Norrby P.-O. ChemCatChem 2009; 1: 152
35 Bedford RB, Brenner PB, Carter E, Cogswell PM, Haddow MF, Harvey JN, Murphy DM, Nunn J, Woodall CH. Angew. Chem. Int. Ed. 2014; 53: 1804
36 O’Brien HM, Manzotti M, Abrams RD, Elorriaga D, Sparkes HA, Davis SA, Bedford RB. Nat. Catal. 2018; 1: 429
37 Fleischauer VE, Muñoz SB. III, Neate PG. N, Brennessel WW, Neidig ML. Chem. Sci. 2018; 9: 1878
38 Scheiper B, Bonnekessel M, Krause H, Fürstner A. J. Org. Chem. 2004; 69: 3943
39 Hamajima A, Isobe M. Org. Lett. 2006; 8: 1205
40 Fürstner A, Hannen P. Chem. Eur. J. 2006; 12: 3006
41 Boukouvalas J, Albert V, Loach RP, Lafleur-Lambert R. Tetrahedron 2012; 68: 9592
42 Seidel G, Laurich D, Fürstner A. J. Org. Chem. 2004; 69: 3950
43 Fürstner A, Leitner A. Angew. Chem. Int. Ed. 2003; 42: 308
44 Cahiez G, Gager O, Habiak V. Synthesis 2008; 2636
45 Scheerer JR, Lawrence JF, Wang GC, Evans DA. J. Am. Chem. Soc. 2007; 129: 8968
46 Guérinot A, Reymond S, Cossy J. Angew. Chem. Int. Ed. 2007; 46: 6521
47 Bensoussan C, Rival N, Hanquet G, Colobert F, Reymond S, Cossy J. Tetrahedron 2013; 69: 7759
48 Gregg C, Gunawan C, Ng AW. Y, Wimala S, Wickremasinghe S, Rizzacasa MA. Org. Lett. 2013; 15: 516
49 Yamada K.-i, Sato T, Hosoi M, Yamamoto Y, Tomioka K. Chem. Pharm. Bull. 2010; 58: 1511
50 Sherry BD, Fürstner A. Acc. Chem. Res. 2008; 41: 1500
51 Lehr K, Fürstner A. Tetrahedron 2012; 68: 7695
52 Fürstner A, De Souza D, Parra-Rapado L, Jensen JT. Angew. Chem. Int. Ed. 2003; 42: 5358
53 Greenhalgh MD, Kolodziej A, Sinclair F, Thomas SP. Organometallics 2014; 33: 5811
54 Greenhalgh MD, Thomas SP. J. Am. Chem. Soc. 2012; 134: 11900
55 Jones AS, Paliga JF, Greenhalgh MD, Quibell JM, Steven A, Thomas SP. Org. Lett. 2014; 16: 5964
56 Plietker B. Angew. Chem. Int. Ed. 2006; 45: 1469
57 Lindermayr K, Plietker B. Angew. Chem. Int. Ed. 2013; 52: 12183
58 Villa M, Jacobi von Wangelin A. Angew. Chem. Int. Ed. 2015; 54: 11906
59 MacNair AJ, Tran M.-M, Nelson JE, Sloan GU, Ironmonger A, Thomas SP. Org. Biomol. Chem. 2014; 12: 5082
60 Ashby EC, Lin JJ. Tetrahedron Lett. 1977; 18: 4481
61 Ashby EC, Lin JJ. J. Org. Chem. 1978; 43: 2567
62 Kano K, Takeuchi M, Hashimoto S, Yoshida Z.-i. J. Chem. Soc. Chem. Commun. 1991; 1728
63 Takeuchi M, Kano K. Organometallics 1993; 12: 2059
64 Leggans EK, Barker TJ, Duncan KK, Boger DL. Org. Lett. 2012; 14: 1428
65 Ishikawa H, Colby DA, Boger DL. J. Am. Chem. Soc. 2008; 130: 420
66 Ishikawa H, Colby DA, Seto S, Va P, Tam A, Kakei H, Rayl TJ, Hwang I, Boger DL. J. Am. Chem. Soc. 2009; 131: 4904
67 Lo JC, Yabe Y, Baran PS. J. Am. Chem. Soc. 2014; 136: 1304
68 Lo JC, Gui J, Yabe Y, Pan C.-M, Baran PS. Nature 2014; 516: 343
69 Gui J, Pan C.-M, Jin Y, Qin T, Lo JC, Lee BJ, Spergel SH, Mertzman ME, Pitts WJ, La Cruz TE, Schmidt MA, Darvatkar N, Natarajan SR, Baran PS. Science 2015; 348: 886
70 Romero D, Olmsted R, Poel TJ, Morge RA, Biles C, Keiser BJ, Kopta LJ, Friis JM, Hosley JD, Stefanski KJ, Wishka DG, Evans DB, Morris J, Stehle RG, Sharma SK, Yagi Y, Voorman RL, Asams WJ, Tarpley WG, Thomas RC. J. Med. Chem. 1996; 39: 3769
71 Zhu K, Shaver MP, Thomas SP. Chem. Sci. 2016; 7: 3031
72 Zhu K, Shaver MP, Thomas SP. Chem. Asian J. 2016; 11: 977
73 Takacs BE, Takacs JM. Tetrahedron Lett. 1990; 31: 2865
74 Takacs JM, Newsome PW, Kuehn C, Takusagawa F. Tetrahedron 1990; 46: 5507
75 Takacs JM, Myoung YC. Tetrahedron Lett. 1992; 33: 317
76 Takacs JM, Boito SC. Tetrahedron Lett. 1995; 36: 2941
77 Takacs JM, Vayalakkada S, Mehrman SJ, Kingsbury CL. Tetrahedron Lett. 2002; 43: 8417
78 Usuda H, Kuramochi A, Kanai M, Shibasaki M. Org. Lett. 2004; 6: 4387
79 Dethe DH, Murhade G. Org. Lett. 2013; 15: 429
80 Meunier B, de Visser SP, Shaik S. Chem. Rev. 2004; 104: 3947
81 Costas M, Mehn MP, Jensen MP, Que L. Chem. Rev. 2004; 104: 939
82 Bordeaux M, Galarneau A, Drone J. Angew. Chem. Int. Ed. 2012; 51: 10712
83 Que LJr, Tolman WB. Nature 2008; 455: 333
84 Abu-Omar MM, Loaiza A, Hontzeas N. Chem. Rev. 2005; 105: 2227
85 Bigi MA, Reed SA, White MC. Nat. Chem. 2011; 3: 216
86 Bigi MA, Liu P, Zou L, Houk KN, White MC. Synlett 2012; 23: 2768
87 Simon JD, Peles DN. Acc. Chem. Res. 2010; 43: 1452
88 Que L, Ho RY. N. Chem. Rev. 1996; 96: 2607
89 Guimond N, Mayer P, Trauner D. Chem. Eur. J. 2014; 20: 9519
90 Davies HM. L, Du Bois J, Yu J.-Q. Chem. Soc. Rev. 2011; 40: 1855
91 Jeffrey JL, Sarpong R. Chem. Sci. 2013; 4: 4092
92 Louillat M.-L, Patureau FW. Chem. Soc. Rev. 2014; 43: 901
93 Michaudel Q, Thevenet D, Baran PS. J. Am. Chem. Soc. 2012; 134: 2547
94 Sharma A, Hartwig JF. Nature 2015; 517: 600
95 Liu K, Li Y, Zheng X, Liu W, Li Z. Tetrahedron 2012; 68: 10333
96 Lv L, Shen B, Li Z. Angew. Chem. Int. Ed. 2014; 53: 4164
97 Fürstner A, Méndez M. Angew. Chem. Int. Ed. 2003; 42: 5355
98 Fürstner A, Kattnig E, Lepage O. J. Am. Chem. Soc. 2006; 128: 9194
99 Petrignet J, Prathap I, Chandrasekhar S, Yadav JS, Grée R. Angew. Chem. Int. Ed. 2007; 46: 6297
100 Mac DH, Samineni R, Sattar A, Chandrasekhar S, Yadav JS, Grée R. Tetrahedron 2011; 67: 9305
101 Molander GA, Shakya SR. J. Org. Chem. 1994; 59: 3445
102 Perron F, Albizati KF. Chem. Rev. 1989; 89: 1617
103 Kunz H, Müller B, Weissmüller J. Carbohyd. Res. 1987; 171: 25
104 van der Does T, Klumpp GH. Tetrahedron Lett. 1986; 27: 519
105 Rueping M, Nachtsheim BJ. Beilstein J. Org. Chem. 2010; 6: 6
106 Gauvreau D, Dolman SJ, Hughes G, O’Shea PD, Davies IW. J. Org. Chem. 2010; 75: 4078
107 Oh E, Kim J, Oh T, Su J, Yun I, Nam K, Min J, Kim W, Koo S. Eur. J. Org. Chem. 2012; 4
108 Blay G, Montesinos-Magraner M, Pedro JR. Arene Chemistry: Reaction Mechanisms and Methods for Aromatic Compounds . Mortier J. Wiley; Hoboken: 2016: 33-58
109 Stadler D, Bach T. Angew. Chem. Int. Ed. 2008; 47: 7557