Assessing the effectiveness of oxidative approaches for the synthesis of aldehydes and ketones from oxidation of iodomethyl group Original Paper First Online: 03 December 2018 Abstract
Owing to excellent selectivity, high yield and stability towards over-reduction and over-oxidation, one of the impressive approaches to synthesize aldehydes and ketones is the oxidation of halomethyl groups. Numerous halomethyl oxidation-based methodologies to afford aldehydes and ketones are disclosed in the literature. Mostly, chloromethyl or bromomethyl group containing substrates have been used in the literature for performing oxidation. There are negligible data available in the literature that addresses the use of iodomethyl group containing substrates for transformation to aldehydes and ketones. In this research work, 110 reactions have been carried out to construct aldehydes and ketones from oxidation of iodomethyl group in benzylic iodides and allylic iodides using numerous well-known approaches reported in the literature. The classical approaches under observation include Sommelet oxidation, Kröhnke oxidation, sodium periodate-mediated oxidative protocol, manganese dioxide-based oxidative approach, Kornblum oxidation and Hass–Bender oxidation. The eco-friendly approaches under observation include periodic acid-based IL protocol, periodic acid in vanadium pentoxide-mediated IL method, hydrogen peroxide in vanadium pentoxide-based approach and bismuth nitrate-promoted IL technique. In this investigation, yield, recyclability, cost-effectiveness, eco-friendliness and over-oxidation are the main parameters which are under observation. Among all these investigated techniques, periodic acid-based IL protocol, periodic acid in vanadium pentoxide-mediated IL method and hydrogen peroxide in vanadium pentoxide-based approach (
aka. Chunbao oxidation protocol) were found to be highly efficient due to the following reasons: these approaches (1) provide excellent yields, (2) do not lead towards over-oxidation, (3) show good recyclability, (4) demonstrate high thermal stability and negligible flammability, and (5) require no special handling. Keywords Aldehydes Ketones Sommelet Kröhnke Iodide Iodomethyl Notes Compliance with ethical standards Conflict of interest
The authors declare that they have no conflict of interest.
Alvarez-Manzaneda EJ, Chahboun R, Torres EC, Alvarez E, Alvarez-Manzaneda R, Haidour A, López JR (2005) Reaction of allylic and benzylic alcohols and esters with PPh3/I2: one-pot synthesis of β, γ-unsaturated compounds. Tetrahedron Lett 46:3755–3759.
https://doi.org/10.1016/j.tetlet.2005.03.132 CrossRef Google Scholar
Armarego W, Chai C (2012) Purification of laboratory chemicals, vol 114. Elsevier, Kidlington. ISBN 9780123821614
Backvall JE, Akermark B, Ljunggren SO (1979) Stereochemistry and mechanism for the palladium (II)-catalyzed oxidation of ethene in water (the Wacker process). J Am Chem Soc 101:2411–2416.
https://doi.org/10.1021/ja00503a029 CrossRef Google Scholar
Barbry D, Champagne P (1996) Fast synthesis of aromatic aldehydes from benzylic bromides without solvent under microwave irradiation. Tetrahedron Lett 37:7725.
https://doi.org/10.1016/0040-4039(96)01734-0 CrossRef Google Scholar
Bayat A, Shakourian-Fard M, Ramezanpour S, Hashemi MM (2015) A green procedure for direct oxidation of organic halides to aldehydes and ketones catalyzed by a molybdate-based catalyst. New J Chem 39:3849–3851.
https://doi.org/10.1039/C4NJ01886A CrossRef Google Scholar
Benington F, Morin RD, Clark LC (1954) Mescaline analogs. I. 2,4,6-trialkoxy-β-phenethylamines. J Org Chem 19:11–16.
https://doi.org/10.1021/jo01366a003 CrossRef Google Scholar
Cardilo P, Orena M, Sandri F (1976) Chromate ion as a synthetically useful nucleophile: a novel synthesis of aldehydes from alkyl halides. J Chem Soc-Chem Comm 6:190.
https://doi.org/10.1039/C39760000190 CrossRef Google Scholar
Das S, Panigrahi AK, Maikap GC (2003) NaIO4–DMF: a novel reagent for the oxidation of organic halides to carbonyl compounds. Tetrahedron Lett 44:1375.
https://doi.org/10.1016/S0040-4039(02)02885-X CrossRef Google Scholar
Faisal M, Larik FA, Saeed A (2018) A highly promising approach for the one-pot synthesis of biscoumarins using HY zeolite as recyclable and green catalyst. J Porous Mat.
https://doi.org/10.1007/s10934-018-0625-0 CrossRef Google Scholar
Goswami S, Jana S, Dey S, Adak AK (2005) A simple and convenient manganese dioxide oxidation of benzyl halides to aromatic aldehydes under neutral condition. Chem Lett 34:194–195.
https://doi.org/10.1246/cl.2005.194 CrossRef Google Scholar
Gupta N, Thakur A, Bhardwaj P (2014) Oxidative transformation of alcohols and organic halides in aqueous solution. New J Chem 38:3749.
https://doi.org/10.1039/C4NJ00393D CrossRef Google Scholar
Hass HB, Bender ML (1949) The reaction of benzyl halides with the sodium salt of 2-Nitropropane. 1 A general synthesis of substituted benzaldehydes. J Am Chem Soc 7:1767–1769.
https://doi.org/10.1021/ja01173a066 CrossRef Google Scholar
Hu YL, Liu QF, Lu TT, Lu M (2010a) Highly efficient oxidation of organic halides to aldehydes and ketones with H5IO6 in ionic liquid [C12mim][FeCl4]. Cat Comm 11:923.
https://doi.org/10.1016/j.catcom.2010.03.017 CrossRef Google Scholar
Hu YL, Liu X, Lu M, Jiang H (2010b) Efficient and convenient oxidation of organic halides to aldehydes and ketones catalyzed by H5IO6/V2O5 in ionic liquid [bmpy][PF6]. J Chin Chem Soc 57:28–33.
https://doi.org/10.1002/jccs.201000005 CrossRef Google Scholar
Itoh A, Kodana T, Inagaki S, Masaki Y (2000) Photooxidation of arylmethyl bromides with mesoporous silica FSM-16. Org Lett 2:2455–2457.
https://doi.org/10.1021/ol0061081 CrossRef PubMed Google Scholar
Khodaei MM, Khosropour AR, Jowkar M (2005) Bi (NO3) 3· 5H
O-TBAF as an efficient reagent for in situ oxidation: dihydropyrimidinone formation from benzyl halides. Syn 2005:1301–1304.
https://doi.org/10.1055/s-2005-861876 CrossRef Google Scholar
Kornblum N, Jones WJ, Anderson GJ (1959) A new and selective method of oxidation. The conversion of alkyl halides and alkyl tosylates to aldehydes. J Am Chem Soc 81:4113–4114.
https://doi.org/10.1021/ja01524a080 CrossRef Google Scholar
Krohnke F (1963) Syntheses using pyridinium salts (IV). Angew Chem Int Ed 2:380–393.
https://doi.org/10.1002/anie.196303801 CrossRef Google Scholar
Larock RC (1989) Comprehensive organic transformations. VCH Publication, NewYork
Li C, Zheng P, Li J, Zhang H, Cui Y, Shao Q, Ji X, Zhang J, Zhao P, Xu Y (2003) The dual roles of oxodiperoxovanadate both as a nucleophile and an oxidant in the green oxidation of benzyl alcohols or benzyl halides to aldehydes and ketones. Angew Chem Int Ed 42:5063.
https://doi.org/10.1002/anie.200351902 CrossRef Google Scholar
LoPachin RM, Gavin T (2014) Molecular mechanisms of aldehyde toxicity: a chemical perspective. Chem Res Toxi 27:1081–1091.
https://doi.org/10.1021/tx5001046 CrossRef Google Scholar
Madathil R, Parkesh R, Draper SM (2006) Oligo (phenylene vinylene)–poly (methylstyrene) hybrids: controlled step-wise molecular wiring of oligo (phenylene vinylene). Tetrahedron Lett 47:2731–2734.
https://doi.org/10.1016/j.tetlet.2006.02.088 CrossRef Google Scholar
Marko IE, Giles PR, Tsukazaki M, Brown SM, Urch CJ (1996) Copper-catalyzed oxidation of alcohols to aldehydes and ketones: an efficient, aerobic alternative. Science 274:2044–2046.
https://doi.org/10.1126/science.274.5295.2044 CrossRef PubMed Google Scholar
Marson CM (1992) Reactions of carbonyl compounds with (monohalo) methyleniminium salts (vilsmeier reagents). Tetrahedrons 48:3659–3726.
https://doi.org/10.1016/S0040-4020(01)92263-X CrossRef Google Scholar
McKillop A, Ford ME (1974) An improved procedure for the conversion of benzyl halides into benzaldehydes. Syn Comm 4:45–50.
https://doi.org/10.1080/00397917408062053 CrossRef Google Scholar
Mukaiyama S, Inanga J, Yamaguchi M (1981) 4-Dimethylaminopyridine N-oxide as an efficient oxidizing agent for alkyl halides. Bull Chem Soc Jpn 54:2221.
https://doi.org/10.1246/bcsj.54.2221 CrossRef Google Scholar
Palamone G, Poggio T, Kapeliouchko V, Laus M, Solvay specialty polymers Italy SpA, (2011) Tetrafluoroethylene polymer particles. U.S. Patent Application 11/739,145
Porcheddu A, Colacino E, Cravotto G, Delogu F, De Luca L (2017) Mechanically induced oxidation of alcohols to aldehydes and ketones in ambient air: revisiting TEMPO-assisted oxidations. Beilstein J Org Chem 13:2049.
https://doi.org/10.3762/bjoc.13.202 CrossRef PubMed PubMedCentral Google Scholar
Rogers RD, Seddon KR (2005) Ionic liquids: fundamentals, progress, challenges, and opportunities. American Chemical Society, Washington
Stellman JM (1998) Encyclopaedia of occupational health and safety. International Labour Office, Geneva
Syper L, Mlochowski J (1984) A convenient oxidation of halomethylarenes and alcohols to aldehydes with dimethyl selenoxide and potassium benzeneselenite. Syn 1984:747–751.
https://doi.org/10.1055/s-1984-30956 CrossRef Google Scholar
Wang A, Jiang H (2010) Palladium-catalyzed direct oxidation of alkenes with molecular oxygen: general and practical methods for the preparation of 1, 2-diols, aldehydes, and ketones. J Org Chem 75:2321–2326.
https://doi.org/10.1021/jo100125q CrossRef PubMed Google Scholar
Wynberg N, Meijer EW (1982) The Reimer–Tiemann reaction. Org React 28:1.
https://doi.org/10.1002/0471264180 CrossRef Google Scholar Copyright information
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