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Search for "benzylic" in Full Text gives 381 result(s) in Beilstein Journal of Organic Chemistry. Showing first 200.

Synthesis and biological activity of methylated derivatives of the Pseudomonas metabolites HHQ, HQNO and PQS

  • Sven Thierbach,
  • Max Wienhold,
  • Susanne Fetzner and
  • Ulrich Hennecke

Beilstein J. Org. Chem. 2019, 15, 187–193, doi:10.3762/bjoc.15.18

Graphical Abstract
  • separated from the N-methylation product by column chromatography and could be isolated in 32% yield. Surprisingly, the N-methylated product under these conditions was not NMe-HHQ (2), but instead a second methylation in the benzylic position had occurred to give N-methyl-2-(1-methylheptyl)-4(1H)-quinolone
  • in the benzylic position could be observed. Instead of direct ortho-metalation, a strategy based on halogen–lithium exchange proved to be more suitable. To this end, HHQ (1) was converted into 3I-HHQ (8) following a literature procedure [21]. 3I-HHQ (8) was then methylated using the MeI/K2CO3
  • conditions to give a mixture of OMe-3I-HHQ (9, 21%) and NMe-3I-HHQ (10, 24%, Scheme 3). Interestingly, in the case of 3I-HHQ (8) the ratio of N-methylation versus O-methylation was almost 1:1 and no further methylation of 10 in the benzylic position was observed. With the methylated compounds 9 and 10 in
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Published 21 Jan 2019

Computational characterization of enzyme-bound thiamin diphosphate reveals a surprisingly stable tricyclic state: implications for catalysis

  • Ferran Planas,
  • Michael J. McLeish and
  • Fahmi Himo

Beilstein J. Org. Chem. 2019, 15, 145–159, doi:10.3762/bjoc.15.15

Graphical Abstract
  • interchangeable (Table 1). Model E: active site of BFDC with (R)-mandelate bound In model E, in which the active site of BFDC contains the inhibitor (R)-mandelate, the hydrogen-bonding network is very similar to that of benzoylformate in model D. However, as shown in Figure 6, the benzylic hydroxy group provides
  • different energies. The superposition of the AP states of the two models (see Supporting Information File 1) shows that the additional hydrogen bond provided by the benzylic hydroxy group of (R)-mandelate (vide supra) contributes significantly to this difference. Further, changing from the sp2 carbonyl
  • carbon to the sp3 benzylic carbon results in a substantial movement of the substituent oxygen which also contributes to the energy difference between the models. According to Table 1 the AP/APH+ forms are the most stable states for models C and E, i.e., BFDC in the absence of ligand and in the presence
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Published 16 Jan 2019

Reactions of 3-(p-substituted-phenyl)-5-chloromethyl-1,2,4-oxadiazoles with KCN leading to acetonitriles and alkanes via a non-reductive decyanation pathway

  • Akın Sağırlı and
  • Yaşar Dürüst

Beilstein J. Org. Chem. 2018, 14, 3011–3017, doi:10.3762/bjoc.14.280

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  • substitution reaction with various alkyl halides to afford mono-, di- or trialkylated acetonitriles [17]. Most recently, Strzalko and co-workers disclose mono and dialkylation of the benzylic carbon of phenylacetonitrile with a poor selectivity by benzyl and methyl halides in the presence of LiHMDS, LDA or n
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Published 10 Dec 2018

Ring-closing-metathesis-based synthesis of annellated coumarins from 8-allylcoumarins

  • Christiane Schultze and
  • Bernd Schmidt

Beilstein J. Org. Chem. 2018, 14, 2991–2998, doi:10.3762/bjoc.14.278

Graphical Abstract
  • catalyze allylic and benzylic oxidation reactions through a radical mechanism [70]. To implement this tandem sequence in the synthesis of pyran-2-one-annellated coumarins 15 an isomerization of the 8-allyl substituent to a prop-1-enyl substituent was first required. When 8-allyl-7-hydroxycoumarin (8a) was
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Published 05 Dec 2018

Synthesis of mono-functionalized S-diazocines via intramolecular Baeyer–Mills reactions

  • Miriam Schehr,
  • Daniel Hugenbusch,
  • Tobias Moje,
  • Christian Näther and
  • Rainer Herges

Beilstein J. Org. Chem. 2018, 14, 2799–2804, doi:10.3762/bjoc.14.257

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  • dinitro compounds, strongly basic conditions have to be applied. Unfortunately, the benzylic position of the bridge is deprotonated under these conditions, leading to a plethora of side products. Formation of the N=N double bond by oxidation of diamines [21][22][23] cannot be applied either, because the
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Published 07 Nov 2018

Assembly of fully substituted triazolochromenes via a novel multicomponent reaction or mechanochemical synthesis

  • Robby Vroemans,
  • Yenthel Verhaegen,
  • My Tran Thi Dieu and
  • Wim Dehaen

Beilstein J. Org. Chem. 2018, 14, 2689–2697, doi:10.3762/bjoc.14.246

Graphical Abstract
  • Information File 1, Figure S1 for NMR comparison), we can make unambiguous conclusions about the regiochemistry of the synthesized compounds 5a, 10 and 11 (Scheme 2). As the product contains a stereocenter, there is a possibility to see diastereotopic splitting of the benzylic protons. In the spectrum of the
  • obtained product 5a starting from 3-nitro-2H-chromene and flavanone, this splitting is not observed (A2 pattern). The benzylic peak of the 2-alkylated product 10 shows an AB splitting pattern and the third regioisomer 11 shows a substantial AX splitting pattern. This striking difference can be rationalized
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Published 22 Oct 2018

Synthesis of dihydroquinazolines from 2-aminobenzylamine: N3-aryl derivatives with electron-withdrawing groups

  • Nadia Gruber,
  • Jimena E. Díaz and
  • Liliana R. Orelli

Beilstein J. Org. Chem. 2018, 14, 2510–2519, doi:10.3762/bjoc.14.227

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  • others, and involve a reduction step which would be incompatible with the presence of nitro or cyano groups [5][13][14][39][68][69][70][71]. The synthetic sequence towards compounds 1 requires the chemoselective arylation of the benzylic amino group of the precursor with active haloaryl derivatives. SNAr
  • increasing the reaction times. The irradiation times were individually adjusted according to the reactivity of the substrates. Interestingly, the 1H NMR spectra of some ortho-substituted derivatives show nonequivalent hydrogens within the benzylic methylenes, which appear as AB spin systems (compounds 1a,b,e
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Published 26 Sep 2018

One-pot synthesis of epoxides from benzyl alcohols and aldehydes

  • Edwin Alfonzo,
  • Jesse W. L. Mendoza and
  • Aaron B. Beeler

Beilstein J. Org. Chem. 2018, 14, 2308–2312, doi:10.3762/bjoc.14.205

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  • all the examples shown in Figure 2 represent new compounds and an extension to this methodology. Conclusion In conclusion, we have developed a general and simple method to access benzylic epoxides through the Corey–Chaykovsky reaction between benzyl alcohols and aldehydes. This method provides
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Published 03 Sep 2018

Synthesis and post-functionalization of alternate-linked-meta-para-[2n.1n]thiacyclophanes

  • Wout De Leger,
  • Koen Adriaensen,
  • Koen Robeyns,
  • Luc Van Meervelt,
  • Joice Thomas,
  • Björn Meijers,
  • Mario Smet and
  • Wim Dehaen

Beilstein J. Org. Chem. 2018, 14, 2190–2197, doi:10.3762/bjoc.14.192

Graphical Abstract
  • deprotonation of the OH group and subsequent chloride loss of 4 an o-quinoid structure 9 is formed in situ, that quickly reacts with the deprotonated thiol 10 via Michael addition (Scheme 3, route A) [28][29][30]. However, as aromatic thiols at the benzylic position are good leaving groups, conversely β
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Published 22 Aug 2018

Hypervalent iodine compounds for anti-Markovnikov-type iodo-oxyimidation of vinylarenes

  • Igor B. Krylov,
  • Stanislav A. Paveliev,
  • Mikhail A. Syroeshkin,
  • Alexander A. Korlyukov,
  • Pavel V. Dorovatovskii,
  • Yan V. Zubavichus,
  • Gennady I. Nikishin and
  • Alexander O. Terent’ev

Beilstein J. Org. Chem. 2018, 14, 2146–2155, doi:10.3762/bjoc.14.188

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  • the examined hypervalent iodine oxidants (PIDA, PIFA, IBX, DMP) PhI(OAc)2 proved to be the most effective; yields of iodo-oxyimides are 34–91%. A plausible reaction pathway includes the addition of an imide-N-oxyl radical to the double C=C bond and trapping of the resultant benzylic radical by iodine
  • chemistry of N-hydroxyimides in combination with hypervalent iodine compounds with formation of imide-N-oxyl radicals. These radicals were used as reagents for the addition to a terminal position of the double bond of styrenes with subsequent iodination of the resulting benzylic radical. It is important to
  • resulting benzylic radicals. Recently, the precursors of N-oxyl radicals, such as N-hydroxyphthalimide (NHPI), N-hydroxysuccinimide (NHSI), N-hydroxybenzotriazole (HOBt) and hydroxamic acids, have been used in the reactions of radical oxygenation of styrenes [45]. Growth of interest is observed concerning
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Published 16 Aug 2018

Applications of organocatalysed visible-light photoredox reactions for medicinal chemistry

  • Michael K. Bogdos,
  • Emmanuel Pinard and
  • John A. Murphy

Beilstein J. Org. Chem. 2018, 14, 2035–2064, doi:10.3762/bjoc.14.179

Graphical Abstract
  • reactions using traditional chemistry and organophotoredox synthesis can offer some interesting options as well. Wu et al. reported the alkylation of unfunctionalised allylic and benzylic sp3 C–H bonds by reaction with Michael acceptors, using blue LEDs and acridinium salts (Scheme 12) [55]. The main
  • advantage is the absence of strong bases like tert-butyllithium (t-BuLi). A very broad scope of Michael acceptors, allylic and benzylic substrates is reported, with an equally broad range of yields achieved (10–99%). Some selectivity is observed when asymmetric alkenes are used. The key to this selectivity
  • iminium radical cation are the keys in the mechanism and to understanding the selectivity of the reaction. In an unsymmetrical reactant, the iminium carries most of the partial positive charge on the benzylic carbon (Figure 11). The radical is not stabilised by being borne on the benzylic carbon, as the
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Published 03 Aug 2018

Preparation and X-ray structure of 2-iodoxybenzenesulfonic acid (IBS) – a powerful hypervalent iodine(V) oxidant

  • Irina A. Mironova,
  • Pavel S. Postnikov,
  • Rosa Y. Yusubova,
  • Akira Yoshimura,
  • Thomas Wirth,
  • Viktor V. Zhdankin,
  • Victor N. Nemykin and
  • Mekhman S. Yusubov

Beilstein J. Org. Chem. 2018, 14, 1854–1858, doi:10.3762/bjoc.14.159

Graphical Abstract
  • to the respective carbonyl compounds with Oxone® (2KHSO5·KHSO4·K2SO4) in nitromethane, acetonitrile, or ethyl acetate [13]. Recent research has revealed the extreme activity of IBS as a catalyst in numerous other oxidations, such as: the oxidation of benzylic and alkane C–H bonds [14], the oxidation
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Published 20 Jul 2018

Recent advances in hypervalent iodine(III)-catalyzed functionalization of alkenes

  • Xiang Li,
  • Pinhong Chen and
  • Guosheng Liu

Beilstein J. Org. Chem. 2018, 14, 1813–1825, doi:10.3762/bjoc.14.154

Graphical Abstract
  • attack of acetates to the exposed re-face establishes the S-configured benzylic C–O bond. Without the hydrogen bonding effect, the same reaction with a diester-containing iodoarene catalyst was explored [55]. The sterically hindered adamantyl-substituted catalysts 17 were demonstrated to be efficient to
  • products. Recently, Jacobsen and co-workers reported a highly enantioselective gem-difluorination of various cinnamic acid derivatives through the same oxidative rearrangement (Scheme 16) [68]. During the catalysts screening, they found that the benzylic unit in the catalysts was essential for a high
  • enantioselectivity (52 vs 53). Moreover, the more electron-deficient 3,4,5-trifluorophenyl analog 54 was found to be less enantioselective. The authors proposed that the benzylic groups can stabilize the cationic intermediates and/or transition states through cation–π interactions, which play an important role in
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Published 18 Jul 2018

β-Hydroxy sulfides and their syntheses

  • Mokgethwa B. Marakalala,
  • Edwin M. Mmutlane and
  • Henok H. Kinfe

Beilstein J. Org. Chem. 2018, 14, 1668–1692, doi:10.3762/bjoc.14.143

Graphical Abstract
  • epoxides underwent reaction with different thiols (aromatic, benzylic, heterocyclic, cyclic and aliphatic (primary, secondary and tertiary)) in CH3CN at room temperature, to afford the corresponding β-hydroxy sulfides in good to excellent yields (Scheme 9). The reaction is compatible with alkyl halides
  • reduction of aromatic β-keto sulfides provided excellent enantioselectivity, the reduction of the corresponding alkyl β-keto sulfides gave low enantioselectivity. Ruano and co-workers reported the asymmetric synthesis of β-hydroxy sulfides via connectivity of a suitably substituted benzylic carbanion with
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Published 05 Jul 2018

Heterogeneous acidic catalysts for the tetrahydropyranylation of alcohols and phenols in green ethereal solvents

  • Ugo Azzena,
  • Massimo Carraro,
  • Gloria Modugno,
  • Luisa Pisano and
  • Luigi Urtis

Beilstein J. Org. Chem. 2018, 14, 1655–1659, doi:10.3762/bjoc.14.141

Graphical Abstract
  • phenols, including some known fragrances (3g–j and 3l) [4][5][6][7], as illustrated in Scheme 2. Conversions exceeding 95% were achieved under the mild conditions illustrated in Scheme 2 with primary aliphatic and benzylic alcohols 1b–h. A notable exception is the low conversion of 4-bromobenzyl alcohol
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Published 03 Jul 2018

Hypervalent organoiodine compounds: from reagents to valuable building blocks in synthesis

  • Gwendal Grelier,
  • Benjamin Darses and
  • Philippe Dauban

Beilstein J. Org. Chem. 2018, 14, 1508–1528, doi:10.3762/bjoc.14.128

Graphical Abstract
  • and PhI(OCOt-Bu)2. These λ3-iodanes have been widely used in atom-transfer reactions, particularly for the generation of metal-bound nitrenes that are highly active species for the aziridination of alkenes and the direct amination of benzylic, allylic or tertiary C(sp3)–H bonds [80][81][82][83][84][85
  • ) [108]. The overall process affords complex nitrogen-containing compounds 92 with very good yields and complete stereocontrol starting from benzylic, allylic and adamantyl substrates. In addition, the preparation of substituted [bis(acyloxy)iodo]arenes following the reaction of iodoarenes with sodium
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Published 21 Jun 2018

[3 + 2]-Cycloaddition reaction of sydnones with alkynes

  • Veronika Hladíková,
  • Jiří Váňa and
  • Jiří Hanusek

Beilstein J. Org. Chem. 2018, 14, 1317–1348, doi:10.3762/bjoc.14.113

Graphical Abstract
  • absence of light. Depending on the temperature, a new reaction pathway involving benzylic group migration, CO2 extrusion and final cycloaddition was proposed (Scheme 4). Kinetics and mechanism of thermal cycloaddition The kinetics and reaction mechanism of the thermal cycloaddition between 4-methyl-3
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Published 05 Jun 2018

A selective removal of the secondary hydroxy group from ortho-dithioacetal-substituted diarylmethanols

  • Anna Czarnecka,
  • Emilia Kowalska,
  • Agnieszka Bodzioch,
  • Joanna Skalik,
  • Marek Koprowski,
  • Krzysztof Owsianik and
  • Piotr Bałczewski

Beilstein J. Org. Chem. 2018, 14, 1229–1237, doi:10.3762/bjoc.14.105

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  • ortho-1,3-dithianylaryl(aryl)methanols leading to ortho-1,3-dithianylaryl(aryl)methanes using the ZnI2-Na(CN)BH3 reductive system (Scheme 1). The use of zinc iodide is critical in this system. It was used for the first time in dichloroethane by Lau et al. to reduce aryl ketones, aldehydes, benzylic
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Published 29 May 2018

One hundred years of benzotropone chemistry

  • Arif Dastan,
  • Haydar Kilic and
  • Nurullah Saracoglu

Beilstein J. Org. Chem. 2018, 14, 1120–1180, doi:10.3762/bjoc.14.98

Graphical Abstract
  • Scheme 7. The acid-catalyzed cleavage of the oxo-bridge of 34 gives benzylic carbocation 35. Consequently, after deprotonation and dehydration, chloro benzotropilium cation 37 undergoes hydrolysis to give 4,5-benzotropone (11) in aqueous reaction media. Using o-xylylene dibromide (38) as starting
  • benzotropylium ion 45. Secondly, 11 is obtained in 18% yield after benzylic bromination of 42 with NBS, followed by in situ elimination reaction of the labile bromide 43 mediated by t-BuOK (Scheme 9). Palladium-catalyzed C–C bond-formation reactions such as Heck and Sonogashira couplings are employed in a wide
  • compound that ionizes in liquid SO2 to the cation 134b. Treatment of cations with nucleophiles that are preferably added to the benzylic position (C-5 or C-9) yielded chloro- and bromo-5H-benzo[7]annulenes 136–143. According to Hückel molecular orbital (HMO) calculations, this observed regiochemistry is
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Published 23 May 2018

Selective carboxylation of reactive benzylic C–H bonds by a hypervalent iodine(III)/inorganic bromide oxidation system

  • Toshifumi Dohi,
  • Shohei Ueda,
  • Kosuke Iwasaki,
  • Yusuke Tsunoda,
  • Koji Morimoto and
  • Yasuyuki Kita

Beilstein J. Org. Chem. 2018, 14, 1087–1094, doi:10.3762/bjoc.14.94

Graphical Abstract
  • benzylic C–H bonds under mild conditions. The unique radical species, generated by the homolytic cleavage of the labile I(III)–Br bond of the in situ-formed bromo-λ3-iodane, initiated benzylic carboxylation with a high degree of selectivity for the secondary benzylic position. Keywords: carboxylic acids
  • ][8]. Benzylic oxidation is of particular interest because it is a convenient direct approach to arylcarbonyl compounds; it has a long history of research and development, and thus is included among the well-investigated C(sp3)–H transformations [9][10][11][12]. To widen the scope, recent studies and
  • reaction systems have been further elaborated to include elegant C–H coupling methodologies. Several important researches that provide a new benzylic C–H coupling strategy have been reported over the past few years, involving the promising catalytic activities of metal complexes [13][14]. On the other hand
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Published 16 May 2018

An overview of recent advances in duplex DNA recognition by small molecules

  • Sayantan Bhaduri,
  • Nihar Ranjan and
  • Dev P. Arya

Beilstein J. Org. Chem. 2018, 14, 1051–1086, doi:10.3762/bjoc.14.93

Graphical Abstract
  • cell lines by interacting non-covalently with the minor groove of the double helical ct-DNA [97]. Barker et al. have designed a series of novel di- and triaryl benzamide MGBs differing in the polar side chain, bonding and substitution patterns and functionalization of benzylic substituents and
  • 35 with a bulky OTBDMS benzylic substituent was found to be the most active agent with (IC50 5.0 μM) followed by conjugate 36 with a chloro substituent (IC50 9.9 μM). Drozdowska et al. reported a series of distamycin analogues 37–41 (Figure 9) as potential minor groove binders and their minor groove
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Published 16 May 2018

Hypervalent iodine(III)-mediated decarboxylative acetoxylation at tertiary and benzylic carbon centers

  • Kensuke Kiyokawa,
  • Daichi Okumatsu and
  • Satoshi Minakata

Beilstein J. Org. Chem. 2018, 14, 1046–1050, doi:10.3762/bjoc.14.92

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  • I2 in a CH2Cl2/AcOH mixed solvent is reported. The reaction was successfully applied to two types of carboxylic acids containing an α-quaternary and a benzylic carbon center under mild reaction conditions. The resulting acetates were readily converted into the corresponding alcohols by hydrolysis
  • solvent (Scheme 1). In subsequent experiments, the method was also found to be applicable to the reaction of benzylic carboxylic acids. The acetates that were produced in the reaction were readily converted into the corresponding alcohols by hydrolysis. Results and Discussion We started our investigation
  • lower than that of a non-cyclic 2i. Using this protocol, 1-adamantanecarboxylic acid was smoothly transformed into the corresponding acetate 2k. In addition to the reaction with respect to tertiary carbon centers, the present method was successfully applied to benzylic carboxylic acid derivatives. For
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Published 15 May 2018

Hypervalent iodine-guided electrophilic substitution: para-selective substitution across aryl iodonium compounds with benzyl groups

  • Cyrus Mowdawalla,
  • Faiz Ahmed,
  • Tian Li,
  • Kiet Pham,
  • Loma Dave,
  • Grace Kim and
  • I. F. Dempsey Hyatt

Beilstein J. Org. Chem. 2018, 14, 1039–1045, doi:10.3762/bjoc.14.91

Graphical Abstract
  • thus we propose a concerted mechanism. The mechanism speculated in Scheme 3 shows a concerted demetallation of the metalloid as the C–C bond is forming. Before the transmetallation of the metalloid group, an interruptive process could be occurring that provides an orbital overlap at the benzylic
  • intramolecular attack on a benzylic methylene with the hypernucleofuge attached (6). The mechanism in Scheme 4 shows the transmetallation occuring instead of being interrupted as in Scheme 3. The combination of both mechanisms (Scheme 3 and Scheme 4) explains how substitution ortho to the iodine (para to the
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Published 14 May 2018

2-Iodo-N-isopropyl-5-methoxybenzamide as a highly reactive and environmentally benign catalyst for alcohol oxidation

  • Takayuki Yakura,
  • Tomoya Fujiwara,
  • Akihiro Yamada and
  • Hisanori Nambu

Beilstein J. Org. Chem. 2018, 14, 971–978, doi:10.3762/bjoc.14.82

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  • -OMe < 5-OAc < 5-Cl < H, 4-OMe < 5-Me < 5-OMe. The oxidation of various benzylic and aliphatic alcohols using a catalytic amount of the most reactive 5-methoxy derivative successfully resulted in moderate to excellent yields of the corresponding carbonyl compounds. The high reactivity of the 5-methoxy
  • derivative at room temperature is a result of the rapid generation of the pentavalent species from the trivalent species during the reaction. 5-Methoxy-2-iodobenzamide would be an efficient and environmentally benign catalyst for the oxidation of alcohols, especially benzylic alcohols. Keywords: hypervalent
  • . The secondary benzylic alcohols 14b–e were oxidized with 17 in much shorter reaction times than those oxidized with 13 to give the corresponding ketones 15b–e in good to excellent yields (Table 2, entries 1–4). Oxidation of the aliphatic secondary alcohol 14f with 17 required a slightly longer
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Published 30 Apr 2018

Enantioselective dioxytosylation of styrenes using lactate-based chiral hypervalent iodine(III)

  • Morifumi Fujita,
  • Koki Miura and
  • Takashi Sugimura

Beilstein J. Org. Chem. 2018, 14, 659–663, doi:10.3762/bjoc.14.53

Graphical Abstract
  • proceed via an SN2 reaction of a cyclic intermediate such as I1, judging from the syn selectivity of the dioxytosylation [52][53]. The attack of the tosylate ion on I1 possibly takes place at the benzylic position or at the methylene carbon atom. The positive charge of I1 may be stabilized by the aryl
  • group and localized at the benzylic position. This may allow the preferential formation of I3 from I1. If I2 was the major intermediate in the pathway leading to 3, the stereochemical purity of 3 would have decreased owing to the facile elimination of the iodonium group [54] at the benzylic position of
  • planar structure of the benzylic cation. Thus, the tosylate ion may act as an effective nucleophile for the SN2 reaction of I1. The stereoface-differentiation in the dioxytosylation reaction using the lactate-derived aryl-λ3-iodanes is similar to that in preceding reactions [14], which include the
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Published 20 Mar 2018
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