Copper-Catalyzed Oxidation of Alkenes and Heterocycles

Ana Leticia García-Cabeza; F. Javier Moreno-Dorado; María J. Ortega; Francisco M. Guerra

doi:10.1055/s-0035-1561649

Synthesis, Table of Contents

Synthesis 2016; 48(15): 2323-2342
DOI: 10.1055/s-0035-1561649

short review

Copper-Catalyzed Oxidation of Alkenes and Heterocycles

Authors

Ana Leticia García-Cabeza

^aDepartamento de Química Orgánica, Facultad de Ciencias, Universidad de Cádiz, Polígono Río San Pedro s/n. 11510 Puerto Real, Cádiz, Spain
F. Javier Moreno-Dorado

^aDepartamento de Química Orgánica, Facultad de Ciencias, Universidad de Cádiz, Polígono Río San Pedro s/n. 11510 Puerto Real, Cádiz, Spain
María J. Ortega

^bDepartamento de Química Orgánica, Facultad de Ciencias del Mar y Ambientales, Universidad de Cádiz, Polígono Río San Pedro s/n. 11510 Puerto Real, Cádiz, Spain Email: francisco.guerra@uca.es
Francisco M. Guerra*

^aDepartamento de Química Orgánica, Facultad de Ciencias, Universidad de Cádiz, Polígono Río San Pedro s/n. 11510 Puerto Real, Cádiz, Spain

Abstract

All articles of this category

Dedicated to Professor Guillermo M. Massanet on the occasion of his 70^th birthday

Abstract

A variety of copper species catalyze the allylic oxidation of olefins and the introduction of an ester group at the α-position of a heterocycle. Both transformations are closely related in terms of reaction conditions and radical species involved. This short review highlights the progress made in these two types of oxidations, emphasizing work that has occurred within the last fifteen years.

1 Introduction

2 General Overview of the Copper-Catalyzed Allylic Oxidation of Olefins

3 Mechanistic Considerations

4 Enantioselective Version of the Allylic Oxidation of Olefins

5 Other Landmarks of the Copper-Catalyzed Oxidation of Olefins

6 α-Oxidation of Heterocycles

7 Reactions in Heterogeneous Phase

8 Applications

9 Summary

Key words

allylic oxidation - α-acyloxylation - copper - Kharasch–Sosnovsky reaction - olefins - heterocycles

Full Text

References

References

1a Roduner E, Kaim W, Sarkar B, Urlacher VB, Pleiss J, Gläser R, Einicke W.-D, Sprenger GA, Beifuss U, Klemm E, Liebner C, Hieronymus H, Hsu S.-F, Plietker B, Laschat S. ChemCatChem 2013; 5: 82
1b White MC. Synlett 2012; 23: 2746
1c Newhouse T, Baran PS. Angew. Chem. Int. Ed. 2011; 50: 3362
1d Giri R, Shi B.-F, Engle KM, Maugel N, Yu J.-Q. Chem. Soc. Rev. 2009; 38: 3242
1e Dick AR, Sanford MS. Tetrahedron 2006; 62: 2439

2a Kharasch MS, Sosnovsky G. J. Am. Chem. Soc. 1958; 80: 756
2b Kharasch MS, Fono A. J. Org. Chem. 1958; 23: 324
2c Kharasch MS, Sosnovsky G, Yang NC. J. Am. Chem. Soc. 1959; 81: 5819

3 Brunel J.-M, Legrand O, Buono G. C. R. Acad. Sci., Ser. IIc 1999; 2: 19
4 Eames J, Watkinson M. Angew. Chem. Int. Ed. 2001; 40: 3567
5 Andrus MB, Lashley JC. Tetrahedron 2002; 58: 845
6 Wei W, Zhang C, Xu Y, Wan X. Chem. Commun. 2011; 47: 10827
7 Sosnovsky G, Yang NC. J. Org. Chem. 1960; 25: 899
8 Farrissei WJ. J. Org. Chem. 1964; 29: 391
9 Beckwith AL. J, Zavitsas AA. J. Am. Chem. Soc. 1986; 108: 8230
10 Walling C, Zavitsas AA. J. Am. Chem. Soc. 1963; 85: 2084
11 Kochi JK, Mains HE. J. Org. Chem. 1965; 30: 1862
12 Andrus MB, Argade AB, Chen X, Pamment MG. Tetrahedron Lett. 1995; 36: 2945
13 Smith K, Hupp CD, Allen KL, Slough GA. Organometallics 2005; 24: 1747
14 Mayoral JA, Rodríguez-Rodríguez S, Salvatella L. Chem. Eur. J. 2008; 14: 9274
15 Denney DB, Napier R, Cammarata A. J. Org. Chem. 1965; 30: 3151
16 Muzart J. Bull. Soc. Chim. Fr. 1986; 65

17a Rispens MT, Zondervan C, Feringa BL. Tetrahedron: Asymmetry 1995; 6: 661
17b Zondervan C, Feringa BL. Tetrahedron: Asymmetry 1996; 7: 1895

18 Gokhale AS, Minidis AB. E, Pfaltz A. Tetrahedron Lett. 1995; 36: 1831
19 Andrus MB, Chen X. Tetrahedron 1997; 53: 16229
20 Andrus MB, Zhou Z. J. Am. Chem. Soc. 2002; 124: 8806
21 Sekar G, DattaGupta A, Singh VK. J. Org. Chem. 1998; 63: 2961

22a Andrus MB, Asgari D, Sclafani JA. J. Org. Chem. 1997; 62: 9365
22b Andrus MB, Asgari D. Tetrahedron 2000; 56: 5775

23a Samadi S, Nazari S, Arvinnezhad H, Jadidi K, Notash B. Tetrahedron 2013; 69: 6679
23b Samadi S, Jadidi K, Notash B. Tetrahedron: Asymmetry 2013; 24: 269

24 Nguyen TP. B, Lee J.-W, Shim WG, Moon H. Microporous Mesoporous Mater. 2008; 110: 560
25 Clark JS, Tolhurst KF, Taylor M, Swallow S. J. Chem. Soc., Perkin Trans. 1 1998; 1167
26 Liu B, Zhu SF, Wang LX, Zhou QL. Tetrahedron: Asymmetry 2006; 17: 634
27 Bayardon J, Sinou D, Guala M, Desimoni G. Tetrahedron: Asymmetry 2004; 15: 3195
28 Clariana J, Comelles J, Moreno-Mañas M, Vallribera A. Tetrahedron: Asymmetry 2002; 13: 1551
29 Zhou Z, Andrus MB. Tetrahedron Lett. 2012; 53: 4518

30a Kawasaki K, Katsuki T. Tetrahedron 1997; 53: 6337
30b Kawasaki K, Shigenobu T, Katsuki T. Synlett 1995; 1245

31 Kohmura Y, Katsuki T. Tetrahedron Lett. 2000; 41: 3941
32 Cheng XM, Zheng ZB, Li N, Qin ZH, Fu B, Wang ND. Tetrahedron: Asymmetry 2008; 19: 2159

33a Ginotra SK, Singh VK. Tetrahedron 2006; 62: 3573
33b Ginotra SK, Singh VK. Org. Biomol. Chem. 2006; 4: 4370

34 Gupta AD, Bhuniya D, Singh VK. Tetrahedron 1994; 50: 13725
35 Malkov AV, Kočovský P. Curr. Org. Chem. 2003; 7: 1737
36 Malkov AV, Bella M, Langer V, Kočovský P. Org. Lett. 2000; 2: 3047

37a Malkov AV, Baxendale IR, Bella M, Langer V, Fawcett J, Russell DR, Mansfield DJ, Valko M, Kočovský P. Organometallics 2001; 20: 673
37b Malkov AV, Pernazza D, Bell M, Bella M, Massa A, Teply F, Meghani P, Kočovský P. J. Org. Chem. 2003; 68: 4727

38 Chelucci G, Loriga G, Murineddu G, Pinna GA. Tetrahedron Lett. 2002; 43: 3601
39 Chelucci G, Iuliano A, Muroni D, Saba A. J. Mol. Catal. A: Chem. 2003; 191: 29
40 Hoang VD. M, Reddy PA. N, Kim T.-J. Organometallics 2008; 27: 1026
41 Malkov AV, Stewart-Liddon AJ. P, Teplý F, Kobr L, Muir KW, Haigh D, Kočovský P. Tetrahedron 2008; 64: 4011
42 Hallett AJ, O’Brien TM, Carter E, Kariuki BM, Murphy DM, Ward BD. Inorg. Chim. Acta 2016; 441: 86
43 Ginotra SK, Singh VK. Tetrahedron 2006; 62: 3573
44 Le Bras J, Muzart J. J. Mol. Catal. A: Chem. 2002; 185: 113
45 Marín-Barrios R, Guerra FM, García-Cabeza AL, Moreno-Dorado FJ, Massanet GM. Tetrahedron 2012; 68: 1105
46 Alvarez LX, Christ ML, Sorokin AB. Appl. Catal. A 2007; 325: 303

47a Le Bras J, Muzart J. Tetrahedron: Asymmetry 2003; 14: 1911
47b Le Bras J, Muzart J. Tetrahedron Lett. 2002; 43: 431

48 Motiwala HF, Gülgeze B, Aubé J. J. Org. Chem. 2012; 77: 7005
49 Clark JS, Roche C. Chem. Commun. 2005; 5175
50 Zhou J, Jin C, Li X, Su W. RSC Adv. 2014; 5: 7232

51a Bayardon J, Sinou D. J. Org. Chem. 2004; 69: 3121
51b Bayardon J, Sinou D. Tetrahedron: Asymmetry 2005; 16: 2965

52 Ang WJ, Lam Y. Org. Biomol. Chem. 2015; 13: 1048
53 Aldea L, Delso I, Hager M, Glos M, García JI, Mayoral JA, Reiser O. Tetrahedron 2012; 68: 3417
54 Meder MB, Gade LH. Eur. J. Inorg. Chem. 2004; 2716
55 Clark JS, Clarke M.-R, Clough J, Blake AJ, Wilson C. Tetrahedron Lett. 2004; 45: 9447
56 Hronowski LJ. J, Szarek WA. J. Med. Chem. 1982; 25: 522
57 Kumar GS, Pieber B, Reddy KR, Kappe CO. Chem. Eur. J. 2012; 18: 6124
58 Wang Q, Geng H, Chai W, Zeng X, Xu M, Zhu C, Fu R, Yuan R. Eur. J. Org. Chem. 2014; 6850
59 Raju KB, Kumar BN, Nagaiah K. RSC Adv. 2014; 4: 50795
60 Wang Q, Zheng H, Chai W, Chen D, Zeng X, Fu R, Yuan R. Org. Biomol. Chem. 2014; 12: 6549
61 Rout SK, Guin S, Ali W, Gogoi A, Patel BK. Org. Lett. 2014; 16: 3086
62 Liu Z.-Q, Zhao L, Shang X, Cui Z. Org. Lett. 2012; 14: 3218
63 Priyadarshini S, Amal Joseph PJ. A, Kantam ML. RSC Adv. 2013; 3: 18283
64 Salavati-Niasari M, Shaterian M. J. Porous Mater. 2008; 15: 581
65 Lashanizadegan M, Zareian Z. Catal. Lett. 2011; 141: 1698
66 Lashanizadegan M, Rayati S, Dejparvar Derakhshan Z. Chin. J. Chem. 2011; 29: 2439
67 Titinchi SJ. J, Von Willingh G, Abbo HS, Prasad R. Catal. Sci. Technol. 2015; 5: 325
68 Carloni S, Frullanti B, Maggi R, Mazzacani A, Bigi F, Sartori G. Tetrahedron Lett. 2000; 41: 8947
69 Ruano D, Diaz-Garcia M, Alfayate A, Sánchez-Sánchez M. ChemCatChem 2015; 7: 674
70 Cancino P, Paredes-Garcia V, Aguirre P, Spodine E. Catal. Sci. Technol. 2014; 4: 2599
71 Yu P, Liu G, Tang R. Curr. Organocatal. 2014; 1: 79
72 Phan NT. S, Vu PH. L, Nguyen TT. J. Catal. 2013; 306: 38
73 Islam SM, Roy AS, Mondal P, Paul S, Salam N. Inorg. Chem. Commun. 2012; 24: 170
74 Mukherjee S, Samanta S, Roy BC, Bhaumik A. Appl. Catal. A 2006; 301: 79
75 Cánepa AL, Chanquía CM, Eimer GA, Casuscelli SG. Appl. Catal. A 2013; 462–463: 8
76 Sun X, Zhao X, Jiang Y, Xu B. J. Chin. Chem. Soc. 2013; 60: 103
77 Gatica JM, García-Cabeza AL, Yeste MP, Marín-Barrios R, González-Leal JM, Blanco G, Cifredo GA, Guerra FM, Vidal H. Chem. Eng. J. 2016; 290: 174
78 Yang M, Peng Q, Xie R, Song G, Lan J, You J. Chin. J. Chem. Eng. 2009; 17: 967
79 Garcia-Cabeza AL, Marin-Barrios R, Moreno-Dorado FJ, Ortega MJ, Massanet GM, Guerra FM. Org. Lett. 2014; 16: 1598
80 García-Cabeza AL, Marín-Barrios R, Moreno-Dorado FJ, Ortega MJ, Vidal H, Gatica JM, Massanet GM, Guerra FM. J. Org. Chem. 2015; 80: 6814
81 Nakamura A, Nakada M. Synthesis 2013; 45: 1421
82 Tan Q, Hayashi M. Org. Lett. 2009; 11: 3314
83 Tanaka T, Tan Q, Kawakubo H, Hayashi M. J. Org. Chem. 2011; 76: 5477
84 Yamatsugu K, Kamijo S, Suto Y, Kanai M, Shibasaki M. Tetrahedron Lett. 2007; 48: 1403
85 Badreddine A, Karym EM, Zarrouk A, Nury T, El Kharrassi Y, Nasser B, Cherkaoui Malki M, Lizard G, Samadi M. Steroids 2015; 99: 119

86a Ur Rahman F, Ur Rahman A, Tan T.-W. J. Chin. Chem. Soc. 2010; 57: 1237
86b Arsenou ES, Koutsourea AI, Fousteris MA, Nikolaropoulos SS. Steroids 2003; 68: 407
86c Salvador JA. R, Sáe Melo ML, Campos Neves AS. Tetrahedron Lett. 1997; 38: 119

87 Schultz AG, Wang A. J. Am. Chem. Soc. 1998; 120: 8259
88 Ho T.-L, Su C.-Y. J. Org. Chem. 2000; 65: 3566
89 Zhang X, Jiang W, Sui Z. J. Org. Chem. 2003; 68: 4523
90 Patin A, Kanazawa A, Philouze C, Greene AE, Muri E, Barreiro E, Costa PC. C. J. Org. Chem. 2003; 68: 3831