Ferrocenephosphonates: Copper-Promoted Synthesis and Further Functionalization

Kmar Abaid; William Erb; Marielle Blot; Thierry Roisnel; Florence Mongin; Soufiane Touil

doi:10.1055/a-1767-3026

Synthesis, Table of Contents

Synthesis 2022; 54(12): 2799-2815
DOI: 10.1055/a-1767-3026

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Ferrocenephosphonates: Copper-Promoted Synthesis and Further Functionalization

Kmar Abaid

^aUniv Rennes, CNRS, ISCR (Institut des Sciences Chimiques de Rennes)-UMR 6226, F-35000 Rennes, France

^bUniversity of Carthage, Faculty of Sciences of Bizerte, Laboratory of Hetero-Organic Compounds and Nanostructured Materials (LR18ES11), 7021, Jarzouna, Tunisia

,

William Erb ∗

^aUniv Rennes, CNRS, ISCR (Institut des Sciences Chimiques de Rennes)-UMR 6226, F-35000 Rennes, France

,

Marielle Blot

^aUniv Rennes, CNRS, ISCR (Institut des Sciences Chimiques de Rennes)-UMR 6226, F-35000 Rennes, France

,

Thierry Roisnel

^aUniv Rennes, CNRS, ISCR (Institut des Sciences Chimiques de Rennes)-UMR 6226, F-35000 Rennes, France

,

Florence Mongin

^aUniv Rennes, CNRS, ISCR (Institut des Sciences Chimiques de Rennes)-UMR 6226, F-35000 Rennes, France

,

Soufiane Touil∗

^bUniversity of Carthage, Faculty of Sciences of Bizerte, Laboratory of Hetero-Organic Compounds and Nanostructured Materials (LR18ES11), 7021, Jarzouna, Tunisia

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Abstract

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Abstract

Ferrocenephosphonates make up an important class of organometallic derivatives with a wide range of useful applications in organic synthesis and coordination chemistry. Here, an approach to ferrocenephosphonates based on a copper-promoted Hirao coupling is reported. Further functionalizations based on regioselective deprotolithiation and both Negishi and Suzuki–Miyaura cross-coupling reactions are also described to reach original derivatives.

Key words

ferrocene - phosphonates - copper catalysis - cross-coupling - deprotolithiation

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References

References

1a Kealy TJ, Pauson PL. Nature 1951; 168: 1039
1b Miller SA, Tebboth JA, Tremaine JF. J. Chem. Soc. 1952; 632

2a Ferrocenes: Homogeneous Catalysis, Organic Synthesis, Materials Science. Togni A, Hayashi T. Wiley-VCH; Weinheim: 1995
2b Gómez Arrayás R, Adrio J, Carretero JC. Angew. Chem. Int. Ed. 2006; 45: 7674
2c Ferrocenes: Ligands, Materials and Biomolecules. Štěpnička P. Wiley; Chichester: 2008
2d Chiral Ferrocenes in Asymmetric Catalysis. Dai L.-X, Hou X.-L. Wiley-VCH; Weinheim: 2010
2e Patra M, Gasser G, Metzler-Nolte N. Dalton Trans. 2012; 41: 6350
2f Scottwell S. Ø, Crowley JD. Chem. Commun. 2016; 52: 2451
2g Astruc D. Eur. J. Inorg. Chem. 2017; 6
2h Patra M, Gasser G. Nat. Rev. Chem. 2017; 1: 66
2i Zhu JC, Cui DX, Li YD, Jiang R, Chen WP, Wang PA. ChemCatChem 2018; 10: 907
2j Ludwig BS, Correia JD. G, Kühn FE. Coord. Chem. Rev. 2019; 396: 22
2k Sierra MA, Casarrubios L, de la Torre MC. Chem. Eur. J. 2019; 25: 7232
2l Singh A, Lumb I, Mehra V, Kumar V. Dalton Trans. 2019; 48: 2840
2m Cunningham L, Benson A, Guiry PJ. Org. Biomol. Chem. 2020; 18: 9329

3a Oms O, Maurel F, Carré F, Bideau JL, Vioux A, Leclercq D. J. Organomet. Chem. 2004; 689: 2654
3b Štěpnička P, Císařová I, Gyepes R. Eur. J. Inorg. Chem. 2006; 926
3c Gawron M, Dietz C, Lutter M, Duthie A, Jouikov V, Jurkschat K. Chem. Eur. J. 2015; 21: 16609

4 Alley SR, Henderson W. J. Organomet. Chem. 2001; 637–639: 216
5 Horký F, Císařová I, Schulz J, Štěpnička P. J. Organomet. Chem. 2019; 891: 44
6 Supej MJ, McLoughlin EA, Hsu JH, Fors BP. Chem. Sci. 2021; 12: 10544

7a Burk MJ, Gross MF. Tetrahedron Lett. 1994; 35: 9363
7b Gschwend B, Pugin B, Bertogg A, Pfaltz A. Chem. Eur. J. 2009; 15: 12993
7c Korb M, Liu X, Walz S, Rosenkranz M, Dmitrieva E, Popov AA, Lang H. Inorg. Chem. 2020; 59: 6147
7d Korb M, Liu X, Walz S, Mahrholdt J, Popov AA, Lang H. Eur. J. Inorg. Chem. 2021; 2017

8a Less RJ, Naseri V, Wright DS. Organometallics 2009; 28: 1995
8b Sasamori T, Hori A, Kaneko Y, Tokitoh N. New J. Chem. 2010; 34: 1560

9a Basra S, de Vries JG, Hyett DJ, Harrison G, Heslop KM, Orpen AG, Pringle PG, von der Luehe K. Dalton Trans. 2004; 1901
9b Korb M, Lang H. Organometallics 2014; 33: 6643
9c Korb M, Schaarschmidt D, Lang H. Organometallics 2014; 33: 2099

10 Rebiere F, Samuel O, Kagan HB. Tetrahedron Lett. 1990; 31: 3121
11 Sanders R, Mueller-Westerhoff UT. J. Organomet. Chem. 1996; 512: 219
12 Bishop JJ, Davison A, Katcher ML, Lichtenberg DW, Merrill RE, Smart JC. J. Organomet. Chem. 1971; 27: 241

13a Corey EJ, Beames DJ. J. Am. Chem. Soc. 1972; 94: 7210
13b Seebach D, Neumann H. Chem. Ber. 1974; 107: 847

14a Herberhold M, Hofmann A, Milius W. J. Organomet. Chem. 1998; 555: 187
14b Herberhold M, Hofmann A, Milius W, de Biani FF, Zanello P. Inorg. Chim. Acta 1998; 273: 24
14c Khobragade DA, Mahamulkar SG, Pospíšil L, Císařová I, Rulíšek L, Jahn U. Chem. Eur. J. 2012; 18: 12267

15 Nayyar B, Koop S, Lutter M, Jurkschat K. Eur. J. Inorg. Chem. 2017; 3233
16 Kowalski K, Zakrzewski J, Long NJ, Suwaki N, Mann DJ, White AJ. P. Dalton Trans. 2006; 571

17a Korb M, Lang H. Chem. Soc. Rev. 2019; 48: 2829
17b Korb M, Lang H. Eur. J. Inorg. Chem. 2022; e202100946

18 Bonini BF, Femoni C, Fochi M, Gulea M, Masson S, Ricci A. Tetrahedron: Asymmetry 2005; 16: 3003

19a Korb M, Swarts PJ, Miesel D, Hildebrandt A, Swarts JC, Lang H. Organometallics 2016; 35: 1287
19b Korb M, Lehrich SW, Lang H. J. Org. Chem. 2017; 82: 3102

20 Khrizanforov M, Strekalova S, Kholin K, Khrizanforova V, Grinenko V, Gryaznova T, Budnikova Y. RSC Adv. 2016; 6: 42701
21 Yu X, Ge B, Zhang Y, Wang X, Wang D. Asian J. Org. Chem. 2016; 5: 1253

22a Hirao T, Masunaga T, Ohshiro Y, Agawa T. Synthesis 1981; 56
22b Toshikazu H, Toshio M, Naoto Y, Yoshiki O, Toshio A. Bull. Chem. Soc. Jpn. 1982; 55: 909

23a Tappe FM. J, Trepohl VT, Oestreich M. Synthesis 2010; 3037
23b Montchamp J.-L. Acc. Chem. Res. 2014; 47: 77
23c Zhang H, Zhang X.-Y, Dong D.-Q, Wang Z.-L. RSC Adv. 2015; 5: 52824
23d Henyecz R, Keglevich G. Curr. Org. Synth. 2019; 16: 523
23e Kanchana US, Diana EJ, Mathew TV, Anilkumar G. ChemistrySelect 2021; 6: 1579

24 Mamane V. Mini-Rev. Org. Chem. 2008; 5: 303
25 Lo C.-Y, Chen C.-H, Tsai TW. T, Zhang L, Lim T.-S, Fann W, Chan JC. C, Luh T.-Y. J. Chin. Chem. Soc. 2010; 57: 539

26a Kadari L, Erb W, Roisnel T, Radha Krishna P, Mongin F. New J. Chem. 2020; 44: 15928
26b Kadari L, Erb W, Halauko YS, Ivashkevich OA, Matulis VE, Lyakhov D, Roisnel T, Radha Krishna P, Mongin F. Eur. J. Inorg. Chem. 2021; 377

27a Gelman D, Jiang L, Buchwald SL. Org. Lett. 2003; 5: 2315
27b Karlstedt NB, Beletskaya IP. Russ. J. Org. Chem. 2011; 47: 1011

28a Huang C, Tang X, Fu H, Jiang Y, Zhao Y. J. Org. Chem. 2006; 71: 5020
28b Rao H, Jin Y, Fu H, Jiang Y, Zhao Y. Chem. Eur. J. 2006; 12: 3636
28c Jiang D, Jiang Q, Fu H, Jiang Y, Zhao Y. Synthesis 2008; 3473

29 Fang C, Wei B, Ma D. Chin. J. Chem. 2021; 39: 2957

30a Karlstedt NB, Anokhin MV, Beletskaya IP. Russ. Chem. Bull. 2013; 62: 2498
30b Ballester J, Gatignol J, Schmidt G, Alayrac C, Gaumont A.-C, Taillefer M. ChemCatChem 2014; 6: 1549
30c Xiong B, Li M, Liu Y, Zhou Y, Zhao C, Goto M, Yin S.-F, Han L.-B. Adv. Synth. Catal. 2014; 356: 781

31a Janssen B, Lutter M, Alnasr H, Krossing I, Jurkschat K. ChemistryOpen 2016; 5: 319
31b Nayyar B, Kapoor R, Lutter M, Alnasr H, Jurkschat K. Eur. J. Inorg. Chem. 2017; 3967

32 Brikci-Nigassa NM, Bentabed-Ababsa G, Erb W, Mongin F. Synthesis 2018; 50: 3615

33a L’Helgoual’ch J.-M, Bentabed-Ababsa G, Chevallier F, Yonehara M, Uchiyama M, Derdour A, Mongin F. Chem. Commun. 2008; 5375
33b Dayaker G, Sreeshailam A, Chevallier F, Roisnel T, Radha Krishna P, Mongin F. Chem. Commun. 2010; 46: 2862

34a Duan X.-F, Zhang Z.-B. Heterocycles 2005; 65: 2005
34b Schlosser M. Angew. Chem. Int. Ed. 2005; 44: 376
34c Schnurch M, Spina M, Khan AF, Mihovilovic MD, Stanetty P. Chem. Soc. Rev. 2007; 36: 1046
34d Schnürch M. Recent Progress on the Halogen Dance Reaction on Heterocycles. In Halogenated Heterocycles: Synthesis, Application and Environment. Iskra J. Springer; Berlin: 2012: 185
34e Erb W, Mongin F. Tetrahedron 2016; 72: 4973

35a Tazi M, Erb W, Halauko YS, Ivashkevich OA, Matulis VE, Roisnel T, Dorcet V, Mongin F. Organometallics 2017; 36: 4770
35b Tazi M, Hedidi M, Erb W, Halauko YS, Ivashkevich OA, Matulis VE, Roisnel T, Dorcet V, Bentabed-Ababsa G, Mongin F. Organometallics 2018; 37: 2207
35c Tazi M, Erb W, Roisnel T, Dorcet V, Mongin F, Low PJ. Org. Biomol. Chem. 2019; 27: 9352
35d Erb W, Roisnel T. Dalton Trans. 2021; 50: 16483
35e Erb W, Wen M, Hurvois JP, Mongin F, Halauko YS, Ivashkevich OA, Matulis VE, Roisnel T. Eur. J. Inorg. Chem. 2021; 3165
35f Wen M, Erb W, Mongin F, Halauko YS, Ivashkevich OA, Matulis VE, Roisnel T, Dorcet V. Organometallics 2021; 40: 1129
35g Zirakzadeh A, Herlein A, Groß MA, Mereiter K, Wang Y, Weissensteiner W. Organometallics 2015; 34: 3820
35h Blockhaus T, Bernhartzeder S, Kempinger W, Klein-Heßling C, Weigand S, Sünkel K. Eur. J. Org. Chem. 2020; 6576

36 Price D, Simpkins NS. Tetrahedron Lett. 1995; 36: 6135

37a Tsukazaki M, Tinkl M, Roglans A, Chapell BJ, Taylor NJ, Snieckus V. J. Am. Chem. Soc. 1996; 118: 685
37b Metallinos C, Szillat H, Taylor NJ, Snieckus V. Adv. Synth. Catal. 2003; 345: 370
37c Genet C, Canipa SJ, O’Brien P, Taylor S. J. Am. Chem. Soc. 2006; 128: 9336
37d Erb W, Roisnel T, Dorcet V. Synthesis 2019; 51: 3205

38a Steffen P, Unkelbach C, Christmann M, Hiller W, Strohmann C. Angew. Chem. Int. Ed. 2013; 52: 9836
38b Nishibayashi Y, Arikawa Y, Ohe K, Uemura S. J. Org. Chem. 1996; 61: 1172

39a Hedidi M, Dayaker G, Kitazawa Y, Tatsuya Y, Kimura M, Erb W, Bentabed-Ababsa G, Chevallier F, Uchiyama M, Gros PC, Mongin F. New J. Chem. 2019; 43: 14898
39b Dayaker G, Erb W, Hedidi M, Chevallier F, Blot M, Gros PC, Hilmersson G, Roisnel T, Dorcet V, Bentabed-Ababsa G, Mongin F. New J. Chem. 2021; 45: 22579

40a Negishi E, King AO, Okukado N. J. Org. Chem. 1977; 42: 1821
40b Negishi E. Acc. Chem. Res. 1982; 15: 340

41 Erb W, Roisnel T. Chem. Commun. 2019; 55: 9132
42 Gong X, Wu J, Meng Y, Zhang Y, Ye L.-W, Zhu C. Green Chem. 2019; 21: 995

43a Miyaura N, Yamada K, Suzuki A. Tetrahedron Lett. 1979; 20: 3437
43b Miyaura N, Suzuki A. Chem. Rev. 1995; 95: 2457

44 Barder TE, Walker SD, Martinelli JR, Buchwald SL. J. Am. Chem. Soc. 2005; 127: 4685

45a Nesmeyanov AN, Reutov OA. Dokl. Akad. Nauk SSSR 1957; 115: 518
45b Little W, Eisenthal R. J. Org. Chem. 1961; 26: 3609

46 Richards CJ, Damalidis T, Hibbs DE, Hursthouse MB. Synlett 1995; 74
47 Kadari L, Roisnel T, Erb W, Krishna PR, Mongin F. Synthesis 2020; 52: 3153

48a Togni A, Pastor SD. J. Org. Chem. 1990; 55: 1649
48b Fukuzawa S.-i, Yamamoto M, Kikuchi S. J. Org. Chem. 2007; 72: 1514

49 Burchat AF, Chong JM, Nielsen N. J. Organomet. Chem. 1997; 542: 281
50 Fulmer GR, Miller AJ. M, Sherden NH, Gottlieb HE, Nudelman A, Stoltz BM, Bercaw JE, Goldberg KI. Organometallics 2010; 29: 2176

51a Srinivas P, Prabhakar S, Chevallier F, Nassar E, Erb W, Dorcet V, Jouikov V, Radha Krishna P, Mongin F. New J. Chem. 2016; 40: 9441
51b Inkpen MS, Du S, Driver M, Albrecht T, Long NJ. Dalton Trans. 2013; 42: 2813

52 Kjonaas RA, Hoffer RK. J. Org. Chem. 1988; 53: 4133

53a Snégaroff K, L’Helgoual’ch J.-M, Bentabed-Ababsa G, Nguyen TT, Chevallier F, Yonehara M, Uchiyama M, Derdour A, Mongin F. Chem. Eur. J. 2009; 15: 10280
53b Kedarnath G, Kumbhare LB, Jain VK, Phadnis PP, Nethaji M. Dalton Trans. 2006; 2714

54 Sollott GP, Mertwoy HE, Portnoy S, Snead JL. J. Org. Chem. 1963; 28: 1090
55 Baillie C, Zhang L, Xiao J. J. Org. Chem. 2004; 69: 7779

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