Iron-catalyzed transformations of diazo compounds

National Science Review

Volumn 1, Issue 4, 2014, Pages 580-603

  Zhu, Shou Fei ^a,b   Zhou, Qi Lin ^a,b  

^a NANKAI UNIVERSITY   (China)

^b Tianjin Engineering Center of Micro Nano Biomaterials and Detection Treatment Technology   (China)

Author keywords

Catalysis; Diazo compounds; Iron; Synthesis

Indexed keywords

EID: 84924959097     PISSN: 20955138     EISSN: 2053714X     Source Type: Journal    
DOI: 10.1093/nsr/nwu019     Document Type: Review

References (96)

1. Nakamura, E and Sato, K. Managing the scarcity of chemical elements. Nat Mater 2011; 10: 158-61.
2. Plietker, B (ed.). Iron Catalysis in Organic Chemistry. Weinheim: Wiley-VCH, 2008.
3. Bolm, C, Legros, J and Le Paih, J et al. Iron-catalyzed reactions in organic synthesis. Chem Rev 2004; 104: 6217-54.
4. Enthaler, S, Junge, K and Beller, M. Sustainable metal catalysis with iron: from rust to a rising star? Angew Chem Int Ed 2008; 47: 3317-21.
5. Sherry, BD and Fürstner, A. The promise and challenge of ironcatalyzed cross coupling. Acc Chem Res 2008; 41: 1500-11.
6. Nakamura, E and Yoshikai, N. Low-valent iron-catalyzed C-C bond formation-addition, substitution, and C-H bond activation. J Org Chem 2010; 75: 6061-7.
7. Sun, CL, Li, BJ and Shi, ZJ. Direct C-H transformation via iron catalysis. Chem Rev 2011; 111: 1293-314.
8. Gopalaiah, K. Chiral iron catalysts for asymmetric synthesis. Chem Rev 2013; 113: 3248-96.
9. For a comprehensive review, see, Doyle, MP, McKervey, MA and Ye, T. Modern Catalytic Methods for Organic Synthesis with Diazo Compounds. Chapters 4 and 5. New York: Wiley, 1998.
10. Ye, T and Mckervey, MA. Organic synthesis with a-diazocarbonyl compounds. Chem Rev 1994; 94: 1091-160.
11. Zhang, ZH and Wang, JB. Recent studies on the reactions of a-diazocarbonyl compounds. Tetrahedron 2008; 64: 6577-605.
12. Lebel, H, Marcoux, JF and Molinaro, C et al. Stereoselective cyclopropanation reactions. Chem Rev 2003; 103: 977-1050.
13. Reissig, HU and Zimmer, R. Donor-acceptor-substituted cyclopropane derivatives and their application in organic synthesis. Chem Rev 2003; 103: 1151-96.
14. Pellissier, H. Recent developments in asymmetric cyclopropanation. Tetrahedron 2008; 64: 7041-95.
15. Wang, CX and Wan, BS. Recent advances in the iron-catalyzed cycloaddition reactions. Chin Sci Bull 2012; 57: 2338-51.
16. Jolly, PW and Pettit, R. Evidence for a novel metal-carbene system. J Am Chem Soc 1966; 88: 5044-5.
17. For reviews, see, Brookhart, M and Studabaker, WB. Cyclopropanes from reactions of transition-metal-carbene complexes with olefins. Chem Rev 1987; 87: 411-32.
18. 2). Top Organomet Chem 2011, 33: 111-38.
19. Seitz, WJ, Saha, AK and Casper, D et al. Iron Lewis acid catalyzed reactions of ethyl diazoacetate with styrene and a-methylstyrene: formation of cyclopropanes with cis selectivity. Tetrahedron Lett 1992; 33: 7755-8.
20. Seitz, WJ, Saha, AK and Hossain, MM. Iron Lewis acid catalyzed cyclopropanation reactions of ethyl diazoacetate and olefins. Organometallics 1993; 12: 2604-8.
21. Seitz, WJ and Hossain, MM. Iron Lewis acid catalyzed reactions of phenyldiazomethane and olefins: formation of cyclopropanes with very high cis selectivity. Tetrahedron Lett 1994; 35: 7561-4.
22. Wolf, JR, Hamaker, CG and Djukic, JP et al. Shape and stereoselective cyclopropanation of alkenes catalyzed by iron porphyrins. J Am Chem Soc 1995; 117: 9194-9.
23. Tagliatesta, P and Pastorini, A. Remarkable selectivity in the cyclopropanation reactions catalysed by a halogenated iron meso-tetraphenylporphyrin. J Mol Catal A: Chem 2003; 198: 57-61.
24. Hamaker, CG, Mirafzal, GA and Woo, LK. Catalytic cyclopropanation with iron(II) complexes. Organometallics 2001; 20: 5171-6.
25. Li, Y, Huang, JS and Zhou, ZY et al. Remarkably stable iron porphyrins bearing nonheteroatom-stabilized carbene or (alkoxycarbonyl) carbenes: isolation, X-ray crystal structures, and carbon atom transfer reactions with hydrocarbons. J Am Chem Soc 2002; 124: 13185-93.
26. Aggarwal, VK, de Vicente, J and Bonnert, RV. Catalytic cyclopropanation of alkenes using diazo compounds generated in situ. A novel route to 2-arylcyclopropylamines. Org Lett 2001; 3: 2785-8.
27. Morandi, B and Carreira, EM. Iron-catalyzed cyclopropanation with trifluoroethylamine hydrochloride and olefins in aqueous media: in situ generation of trifluoromethyl diazomethane. Angew Chem Int Ed 2010; 49: 938-41.
28. Morandi, B, Cheang, J and Carreira, EM. Iron-catalyzed preparation of trifluoromethyl substituted vinyl-and alkynylcyclopropanes. Org Lett 2011; 13: 3080-1.
29. Morandi, B, Dolva, A and Carreira, EM. Iron-catalyzed cyclopropanation with glycine ethyl ester hydrochloride in water. Org Lett 2012; 14: 2162-3.
30. Morandi, B and Carreira, EM. Iron-catalyzed cyclopropanation in 6 M KOH with in situ generation of diazomethane. Science 2012; 335: 1471-4.
31. For highlights, see, Kaschel, J, Schneider, TF and Werz, DB. One pot, two phases: iron-catalyzed cyclopropanation with in situ generated diazomethane. Angew Chem Int Ed 2012; 51: 7085-6.
32. Gross, Z, Galili, N and Simkhovich, L. Metalloporphyrin catalyzed asymmetric cyclopropanation of olefins. Tetrahedron Lett 1999; 40: 1571-4.
33. Du, GD, Andrioletti, B and Rose, E et al. Asymmetric cyclopropanation of styrene catalyzed by chiral macrocyclic iron(II) complexes. Organometallics 2002; 21: 4490-5.
34. Le Maux, P, Juillard, S and Simonneaux, G. Asymmetric synthesis of trifluoromethylphenyl cyclopropanes catalyzed by chiral metalloporphyrins. Synthesis 2006; 1701-4.
35. Lai, TS, Chan, FY and So, PK et al. Alkene cyclopropanation catalyzed by Halterman iron porphyrin: participation of organic bases as axial ligands. Dalton Trans 2006; 4845-51.
36. 2-symmetrical chiral porphyrin: superiority of cobalt over iron. J Org Chem 2007; 72: 5931-4.
37. Nicolas, I, Roisnel, T and Le Maux, P et al. Asymmetric intermolecular cyclopropanation of alkenes by diazoketones catalyzed by Halterman iron porphyrins. Tetrahedron Lett 2009; 50: 5149-51.
38. Nicolas, I, Le Maux, P and Simonneaux, G. Synthesis of chiral water-soluble metalloporphyrins (Fe, Ru): new catalysts for asymmetric carbene transfer in water. Tetrahedron Lett 2008; 49: 5793-6.
39. Le Maux, P, Nicolas, I and Chevance, S et al. Chemical reactivity of 6-diazo-5-oxo-L-norleucine (DON) catalyzed by metalloporphyrins (Fe, Ru). Tetrahedron 2010; 66: 4462-8.
40. Coelho, PS, Brustad, EM and Kannan, A et al. Olefin cyclopropanation via carbene transfer catalyzed by engineered cytochrome P450 enzymes. Science 2013; 339: 307-10.
41. For highlights, see, Roiban, GD and Reetz, MT. Enzyme promiscuity: using a P450 enzyme as a carbene transfer catalyst. Angew Chem Int Ed 2013; 52: 5439-40.
42. Gross, Z, Simkhovich, L and Galili, N. First catalysis by corrole metal complexes: epoxidation, hydroxylation, and cyclopropanation. Chem Commun 1999; 599-600.
43. Sharma, VB, Jain, SL and Sain, B. Metallophthalocyanines as potent catalysts for cyclopropanation of olefins with ethyldiazoacetate. Catal Lett 2004; 94: 57-9.
44. Sharma, VB, Jain, SL and Sain, B. Metallophthalocyanines catalyzed cyclopropanation of olefins with trimethylsilyldiazomethane: a facile and stereoselective synthesis of silylcyclopropanes. Catal Commun 2006; 7: 454-6.
45. Edulji, SK and Nguyen, ST. Catalytic olefin cyclopropanation using μ-oxobis[(salen)iron(III)] complexes. Organometallics 2003; 22: 3374-81.
46. Edulji, SK and Nguyen, ST. Substrate scope in the olefin cyclopropanation reaction catalyzed by μ-oxo-bis[(salen)iron(III)] complexes. Pure Appl Chem 2004; 76: 645-9.
47. 2-terpyridines: synthesis, characterization and use in catalytic asymmetric cyclopropanation of styrenes. Inorg Chim Acta 2009; 362: 3267-73.
48. Mbuvi, HM and Woo, LK. Addition of carbenes derived from aryldiazoacetates to arenes using chloro(tetraphenylporphyrinato)iron as catalyst. J Porphyrins Phthalocyanines 2009; 13: 136-52.
49. Wang, SR, Zhu, CY and Sun, XL et al. Reaction of allylic phosphoranes with iron porphyrin carbenoids: efficient, selective, and catalytic intermolecular formal carbenoid insertion into olefinic C-H bonds. JAmChem Soc 2009; 131: 4192-3.
50. Wang, P, Ling, L and Liao, SH, et al. Reactions of iron carbenes with a, β-unsaturated esters by using an umpolung approach: mechanism and applications. Chem Eur J 2013; 19: 6766-73.
51. For a review, see, Sun, XL, Zheng, JC and Tang, Y. Iron carbenoid-mediated ylide reactions. Pure Appl Chem 2010; 82: 625-34.
52. Wang, P, Liao, SH and Wang, SR et al. Reaction of trisubstituted alkenes with iron porphyrin carbenes: facile synthesis of tetrasubstituted dienes and cyclopentadienes. Chem Commun 2013; 49: 7436-8.
53. Wang, P, Liao, SH and Zhu, JB et al. Iron-catalyzed three-component reaction: multiple C-C bond cleavages and reorganizations. Org Lett 2013; 15: 3606-9.
54. For recent reviews, see, Davies, HML and Manning, JR. Catalytic C-H functionalization by metal carbenoid and nitrenoid insertion. Nature 2008; 451: 417-24.
55. Giri, R, Shi, BF and Engle, KM, et al. Transition metal-catalyzed C-H activation reactions: diastereoselectivity and enantioselectivity. Chem Soc Rev 2009; 38: 3242-72.
56. Doyle, MP, Duffy, R and Ratnikov, M, et al. Catalytic carbene insertion into C-H bonds. Chem Rev 2010; 110: 704-24.
57. Mbuvi, HM and Woo, LK. Catalytic C-H insertions using iron(III) porphyrin complexes. Organometallics 2008; 27: 637-45.
58. Lian, YJ and Davies, HML. Rhodium-catalyzed [3 + 2] annulation of indoles. J Am Chem Soc 2010; 132: 440-1.
59. Cai, Y, Zhu, SF and Wang, GP et al. Iron-catalyzed C-H functionalization of indoles. Adv Synth Catal 2011; 353: 2939-44.
60. Aviv, I and Gross, Z. Iron corroles and porphyrins as very efficient and highly selective catalysts for the reactions of α-diazo esters with amines. Synlett 2006; 951-3.
61. Baumann, LK, Mbuvi, HM and Du, GD, et al. Iron porphyrin catalyzed N-H insertion reactions with ethyl diazoacetate. Organometallics 2007; 26: 3995-4002.
62. Aviv, I and Gross, Z. Iron(III) corroles and porphyrins as superior catalysts for the reactions of diazoacetates with nitrogen-or sulfur-containing nucleophilic substrates: synthetic uses and mechanistic insights. Chem Eur J 2008; 14: 3995-4005.
63. Aviv, I and Gross, Z. Iron porphyrins catalyze the synthesis of non-protected amino acid esters from ammonia and diazoacetates. Chem Commun 2006; 4477-9.
64. Mbuvi, HM, Klobukowski, ER and Roberts, GM et al. O-H insertion and tandem N-H insertion/cyclization reactions using an iron porphyrin as catalyst with diazo compounds as carbene sources. J Porphyrins Phthalocyanines 2010; 14: 284-92.
65. Wang, ZJ, Peck, NE and Renata, H et al. Cytochrome P450-catalyzed insertion of carbenoids into N-H bonds. Chem Sci 2014; 5: 598-601.
66. Holzwarth, MS, Alt, I and Plietker, B. Catalytic activation of diazo compounds using electron-rich, defined iron complexes for carbene-transfer reactions. Angew Chem Int Ed 2012; 51: 5351-4.
67. Muthusamy, S, Babu, SA and Gunanathan, C. Indium triflate: a mild and efficient Lewis acid catalyst for O-H insertion reactions of α-diazo ketones. Tetrahedron Lett 2002; 43: 3133-6.
68. Yue, YL, Wang, YH and Hu, WH. Regioselectivity in Lewis acids catalyzed X-H (O, S, N) insertions of methyl styryldiazoacetate with benzyl alcohol, benzyl thiol, and aniline. Tetrahedron Lett 2007; 48: 3975-7.
69. Zhu, SF, Cai, Y and Mao, HX et al. Enantioselective iron-catalysed O-H bond insertions. Nat Chem 2010; 2: 546-51.
70. For a review, see, Zhu, SF and Zhou, QL. Enantioselective transition-metalcatalyzed heteroatom-hydrogen bonds insertion reactions. Acc Chem Res 2012; 45: 1365-77.
71. Maier, TC and Fu, GC. Catalytic enantioselective O-H insertion reactions. J Am Chem Soc 2006; 128: 4594-5.
72. Zhu, SF, Chen, C and Cai, Y et al. Catalytic asymmetric reaction with water: enantioselective synthesis of α-hydroxyesters by copper-carbenoid O-H insertion reaction. Angew Chem Int Ed 2008; 47: 932-4.
73. Kirmse, W and Kapps, M. Reaktionen des diazomethans mit diallylsulfid und allyläthern unter kupfersalz-katalyse. Chem Ber 1968; 101: 994-1003.
74. Doyle, MP, Griffin, JH and Chinn, MS, et al. Rearrangements of ylides generated from reactions of diazo compounds with allyl acetals and thioketals by catalytic methods. Heteroatom acceleration of the [2, 3]-sigmatropic rearrangement. J Org Chem 1984; 49: 1917-25.
75. Carter, DS and Van Vranken, DL. Iron-catalyzed Doyle-Kirmse reaction of allyl sulfides with (trimethylsilyl)diazomethane. Org Lett 2000; 2: 1303-5.
76. Prabharasuth, R and Van Vranken, DL. Iron-catalyzed reaction of propargyl sulfides and trimethylsilyldiazomethane. J Org Chem 2001; 66: 5256-8.
77. Mirafzal, GA, Cheng, GL and Woo, LK. A new and efficient method for the selective olefination of aldehydes with ethyl diazoacetate catalyzed by an iron(II) porphyrin complex. J Am Chem Soc 2002; 124: 176-7.
78. Chinnusamy, T, Rodionov, V and Kühn, FE et al. Update: an efficient synthesis of poly(ethylene glycol)-supported iron(II) porphyrin using a click reaction and its application for the catalytic olefination of aldehydes. Adv Synth Catal 2012; 354: 1827-31.
79. Chen, Y, Huang, L and Ranade, MA et al. Iron(III) and ruthenium(II) porphyrin complex-catalyzed selective olefination of aldehydes with ethyl diazoacetate. J Org Chem 2003; 68: 3714-7.
80. Sun, Wand Kühn, FE. Efficient aldehyde olefination reactions catalyzed by an iron porphyrin complex in an ionic liquid. Tetrahedron Lett 2004; 45: 7415-8.
81. Sharma, VB, Jain, SL and Sain, B. An efficient method for the olefination of aldehydes with ethyl diazoacetate using iron(II) phthalocyanine as catalyst. Catal Lett 2004; 98: 141-3.
82. Aggarwal, VK, Fulton, JR and Sheldon, CG et al. Generation of phosphoranes derived from phosphites. A new class of phosphorus ylides leading to high E selectivity with semi-stabilizing groups in Wittig olefinations. J Am Chem Soc 2003; 125: 6034-5.
83. Chen, Y, Huang, L and Zhang, XP. Acid-promoted olefination of ketones by an iron(III) porphyrin complex. Org Lett 2003; 5: 2493-6.
84. Cheng, G, Mirafzal, GA and Woo, LK. Iron porphyrin-catalyzed olefination of carbonyl compounds with ethyl diazoacetate. Organometallics 2003; 22: 1468-74.
85. Chen, Y, Huang, L and Zhang, XP. Efficient and stereoselective synthesis of β-trifluoromethyl α, β-unsaturated esters via iron(III) porphyrin-catalyzed olefination of Ketones. J Org Chem 2003; 68: 5925-9.
86. Wang, P, Liu, CR and Sun, XL et al. A newly-designed PE-supported arsine for efficient and practical catalytic Wittig olefination. Chem Commun 2012; 48: 290-2.
87. Li, CY, Wang, XB and Sun, XL et al. Iron porphyrin-catalyzed olefination of ketenes with diazoacetate for the enantioselective synthesis of allenes. J Am Chem Soc 2007; 129: 1494-5.
88. Kuninobu, Y, Nishi, Mand Takai, K. Iron-catalyzed synthesis of glycine derivatives via carbon-nitrogen bond cleavage using diazoacetate. Chem Commun 2010; 46: 8860-2.
89. Ma, CQ, Xing, D and Zhai, CWet al. Iron porphyrin-catalyzed three-component reaction of ethyl diazoacetate with aliphatic amines and β, γ-unsaturated α-keto esters. Org Lett 2013; 15: 6140-3.
90. For a review on the trapping of ylide intermediates, see, Guo, X and Hu, WH. Novel multicomponent reactions via trapping of protic onium ylides with electrophiles. Acc Chem Res 2013; 46: 2427-40.
91. Mayer, MF and Hossain, MM. Catalytic preparation of aziridines with an iron Lewis acid. J Org Chem 1998; 63: 6839-44.
92. Mayer, MF, Wang, QW and Hossain, MM. An explanation for the apparent cis-aziridine selectivity in the iron Lewis acid-catalyzed reaction of Nbenzylidene aniline and ethyl diazoacetate. J Organomet Chem 2001; 630: 78-83.
93. Redlich, M and Hossain, MM. Synthesis of asymmetric iron-pybox complexes and their application to aziridine forming reactions. Tetrahedron Lett 2004; 45: 8987-90.
94. Mahmood, SJ, Saha, AK and Hossain, MM. Iron Lewis acid catalyzed reactions of phenyldiazomethane with aromatic aldehydes. Tetrahedron 1998; 54: 349-58.
95. Mahmood, SJ and Hossain, MM. Iron Lewis acid catalyzed reactions of aromatic aldehydes with ethyl diazoacetate: unprecedented formation of 3-hydroxy-2-arylacrylic acid ethyl esters by a unique 1, 2-aryl shift. J Org Chem 1998; 63: 3333-6.
96. Benito-Garagorri, D, Wiedermann, J and Pollak, M et al. Iron(II) complexes bearing tridentate PNP pincer-type ligands as catalysts for the selective formation of 3-hydroxyacrylates from aromatic aldehydes and ethyl diazoacetate. Organometallics 2007; 26: 217-22.