Iron-catalyzed synthesis of heterocycles

Majumdar, K. C.; De, Nirupam; Ghosh, Tapas; Roy, B.

doi:10.1016/j.tet.2014.04.025

Cited by 62 publications

(24 citation statements)

References 335 publications

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“…1083 Some examples have also been included in an account article by Wang. 1084 Among other synthetic principles this involves reactions at carbonyl and carbonyl analogue groups as described in the following section.…”

Section: Synthesis Of Heterocyclesmentioning

confidence: 99%

Iron Catalysis in Organic Synthesis

2015

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Section: Synthesis Of Heterocyclesmentioning

confidence: 99%

Iron Catalysis in Organic Synthesis

2015

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“…Development of homogeneous catalysis using iron as the active metal center is one of the most important issues for the sustainable development of chemical production of useful organic compounds, not using rare metal resources [18]. Therefore, many chemists started development of the chemical procedure of iron catalysts [19][20][21]. However, it is a drawback that iron compounds usually form high-spin paramagnetic species, which are difficult to determine the structures and are unstable attributed to the unpaired electron, decreasing strength of the bonding interactions between iron atom and ligand [22].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Structure of Homoleptic Iron Complex Bearing Pincer-Type 1,2,3-Triazol-5-ylidene

Iwasaki¹,

Koga²

2016

Organic Chem Curr Res

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structure of pyridine-bridged 1,2,3-triazol-5-ylidene (3a, 3b), which are prepared from the corresponding bis(1,2,3-triazole) (1a, 1b) as the starting material, via the methylated bis(1,2,3-triazolium) salts (2a, 2b). The compounds 2a and 2b are easily reduced to form 3a and 3b, respectively, in good yields (Scheme 2) [23]. They are rare examples of the isolated MIC. The X-ray crystallography and DFT calculations of 3a indicated its characteristic amphiphilic nature; because it has an expanded π-conjugated plane including one pyridine and two carbene rings, the stabilized π*-orbital easily accept a single unpaired electron to form anionic radical species in part, despite the fact that carbene carbons are strong σ-donor [24]. Here, we successfully synthesized and determined the tridentate MIC complex of iron. Unexpectedly, even if stoichiometric amount of the carbene ligand was added to iron halides, two molecules of the carbene coordinated to form dicationic homoleptic iron complex 4 with stepwise liberation of two halide anions from iron halides. Materials and Methods All experiments were carried out under an inert gas atmosphere using standard Schlenk techniques and a glove box (MBraun UniLab) unless otherwise noted. THF, toluene, hexane, and benzene-d 6 were distilled from benzophenone ketyl and stored under a nitrogen atmosphere. Organic reagents used for coupling reactions were distilled just before use. The starting materials, 2,6-bisacetylpyridine [25] and 2-azido-2,6-diisopropylbenzene [26] were prepared according to the literature. 1 H NMR (400 MHz) and 13 C NMR (100 MHz) spectra were recorded on a Bruker AVANCE III HD 400 MHz spectrometer at room temperature in CDCl 3 or acetonitrile-d 3. Chemical shifts (δ) were recorded in ppm from the internal standard. IR spectra were recorded in cm-1 on a PERKIN ELMER Spectrum Two spectrometer equipped with a universal diamond ATR.

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“…8,137.9,137.1,135.1,134.9,134.1,134.0,130.1,129.8,129.6,129.4,129.3,128.3,126.8,123.6,122.6,88.4,79.1,21.2,21.1. MS (EI,70 eV. m/z (relative intensity)): 520 (14), 313 (17), 281 (20), 207 (100) 6, 138.6, 137.6, 135.0, 133.9, 133.8, 132.5, 130.1, 130.0, 129.7, 128.5, 124.1, 122.8, 113.6, 91.7, 78.8, 55.2, 21. 4, 134.7, 134.2, 133.5, 133.3, 133.0, 130.2, 129.3, 128.9, 128.5, 128.2, 128.0, 127.7, 127.6, 127.5, 126.6, 126.4, 125.9, 125.8, 124.6, 92.2, 79.3. MS (EI, 70 eV.…”

Section: -(4-chlorophenyl)-34-bis((4-fluorophenyl)selanyl)-25-dihymentioning

confidence: 99%

“…16 The use of iron salts in organic synthesis has emerged as a powerful methodology to promote several transformations: (i) cross coupling reaction of Grignard reagents with organic electrophiles; 17 (ii) carbon-heteroatom (C-N, C-O, C-S and C-Se) bond formation; 18 (iii) heteroatom-heteroatom and carbon-carbon bond formation; 19 and (iv) for the synthesis of heterocycle compounds. 20 Compared with other transition metals, the iron chemistry has been reported to have many advantages such as relative stability, abundance, low toxicity, economic and ecological advantages, and excellent tolerance towards various functional groups. 21 In this article, we propose a protocol for the preparation of 3,4-bis(organoselanyl)-2,5-dihydrofurans 3 from 1,4-butyne-diols 1 and diorganyl diselenides 2 using iron salt as catalyst (Scheme 1).…”

mentioning

confidence: 99%

Iron-Catalyzed Cyclization of Alkynols with Diorganyl Diselenides: Synthesis of 2,5-Dihydrofuran, 3,6-Dihydro-2H-pyran, and 2,5-Dihydro-1H-pyrrole Organoselanyl Derivatives

2015

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An iron-catalyzed system, using diorganyl diselenides as an organoselenium source, was used for the cyclization of 1,4-butyne-diols in the preparation of 3,4-bis(organoselanyl)-2,5-dihydrofurans. The optimized reaction conditions are compatible with many functional groups in 1,4-butyne-diols and diorganyl diselenides. In addition, this catalyst system was also efficient with diorganyl disulfides, but it did not work for diorganyl ditellurides. The same reaction conditions were also extended to pentyne-1,5-diol for the preparation of 4,5-bis(organoselanyl)-3,6-dihydro-2H-pyrans and to 4-amino-butynol for the preparation of 2,5-dihydro-1H-pyrrole derivatives. The synthetic utility of these heterocycles was studied using 5-bis(organoselanyl)-3,6-dihydro-2H-pyrans as substrate in a Kumada-type cross-coupling reaction.

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Iron-catalyzed synthesis of heterocycles

Cited by 62 publications

References 335 publications

Iron Catalysis in Organic Synthesis

Iron Catalysis in Organic Synthesis

Synthesis and Structure of Homoleptic Iron Complex Bearing Pincer-Type 1,2,3-Triazol-5-ylidene

Iron-Catalyzed Cyclization of Alkynols with Diorganyl Diselenides: Synthesis of 2,5-Dihydrofuran, 3,6-Dihydro-2H-pyran, and 2,5-Dihydro-1H-pyrrole Organoselanyl Derivatives

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