Palladium-Catalyzed Cross-Methylation of Haloarenes Possessing Active Hydrogen Atoms by Intramolecularly Stabilized Dimethylindium and Dimethylaluminum Reagents

Jaber, Nimer; Gelman, Dmitri; Schumann, Herbert; Dechert, Sebastian; Blum, Jochanan

doi:10.1002/1099-0690(200205)2002:10<1628::aid-ejoc1628>3.0.co;2-c

Cited by 34 publications

(4 citation statements)

References 28 publications

(18 reference statements)

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“…Intramolecularly stabilized dialkyl indium complexes 18 and 19 , which can be readily prepared from the alcoholysis of R 3 In with HOCH 2 CH 2 N(Me) 2 or the metathesis of R 2 InCl with LiCH 2 CH 2 N(Me) 2 , were found to efficiently cross-couple with aryl halides under nickel and palladium − catalysis (Scheme ). The mildness of the organoindium reagents rendered the protocol amenable to functional groups such as carbonyl, nitro, cyano, and hydroxy groups.…”

Section: Miscellaneous Organoindium Reagentsmentioning

confidence: 99%

Organoindium Reagents: The Preparation and Application in Organic Synthesis

et al. 2012

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allylation performed in aqueous media, an efficient synthesis of highly functionalized lactones was realized in good yields (64− 77%, Scheme 29). 238 However, the chirality installed during the first step almost had no influence on the second step, thus resulting in poor diastereoselectivity in the subsequent allylation reaction (1:1−2:1 dr).In situ formation of aldehyde from the oxidation of alcohol followed by one-pot indium-mediated allylation also provides an alternative method for the synthesis of homoallylic alcohol. Recently, Yadav and co-workers developed such a one-pot sequence by using chloramines-T (sodium salt of Nchlorotosylamide) as oxidant in the presence of a catalytic amount of FeCl 3 in CH 2 Cl 2 , giving rise to homoallylic alcohols in good to excellent yields (Scheme 30). 239 It is noteworthy that the generated byproduct of TsNH 2 (from the reduction of chloramines-T) may react with the in situ-formed aldehydes to give intermediates of N-tosylimines in the presence of 4 Å molecular sieve under refluxing; the thus-formed N-tosylimines subsequently underwent one-pot indium-mediated allylation to produce homoallylic amines in 60−80% yields. Later, a similar one-pot, two-step sequence for the synthesis of homoallylic alcohols via a galactose oxidase-mediated chemo-enzymatic oxidation of benzyl and cinnamyl alcohols to the corresponding Scheme 23 Scheme 24 Scheme 25 Scheme 26 Scheme 27 Scheme 28 Scheme 29 Scheme 30 Chemical Reviews Review dx.

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Section: Miscellaneous Organoindium Reagentsmentioning

confidence: 99%

Organoindium Reagents: The Preparation and Application in Organic Synthesis

et al. 2012

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“…The coordination number of aluminum is five and the coordination geometry corresponds to a distorted trigonal bipyramid with the coordinating oxygen and nitrogen atoms in the axial positions. [58].…”

Section: Salt Metathesis With Ag[wca]mentioning

confidence: 78%

In search for a pentacoordinated monoorgano stannyl cation

Nechaev

Chernov

Portnyagin

et al. 2010

Journal of Organometallic Chemistry

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“…The combined organic extracts were washed with 5% sodium bisulfite (10 mL) and brine (10 mL), dried over MgSO 4 , and concentrated. Products were purified by SiO 2 chromatography eluted with EtOAc/hexanes to give 0.530 g (91%) of 2-bromo-3,5-dihydroxybenzoic acid ( 7 ), 0.562 g (96%) of 1-bromo-2,4,6-trimethoxybenzene ( 8 ), mp 93.5−95.0 °C (lit . mp 98−99 °C), or 0.545 g (90%) of N -(4-bromophenyl)morpholine ( 9 ), mp 112−115 °C (lit .…”

Section: Methodsmentioning

confidence: 99%

A Xerogel-Sequestered Selenoxide Catalyst for Brominations with Hydrogen Peroxide and Sodium Bromide in an Aqueous Environment

et al. 2008

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4-(Hydroxymethyl)phenyl benzyl selenoxide (4) sequestered in a halide-permeable, Class II xerogel formed from 10/90 (mol/mol) 3-aminopropyltriethoxysilane/tetraethoxysilane catalyzes the bromination of organic substrates (4-pentenoic acid, 3,5-dihydroxybenzoic acid, 1,3,5-trimethoxybenzene, N-phenylmorpholine, and N,N-dimethylaniline) with NaBr and H2O2. Catalyst performance (reaction rate) when sequestered within the halide-permeable xerogel is 23-fold greater in comparison to xerogel-free catalyst in solution. The catalyst is easily separated from the reaction mixture via filtration and the recovered catalyst can be reused without loss of activity through formation of the first 80 mol of product per mole of catalyst.

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Palladium-Catalyzed Cross-Methylation of Haloarenes Possessing Active Hydrogen Atoms by Intramolecularly Stabilized Dimethylindium and Dimethylaluminum Reagents

Cited by 34 publications

References 28 publications

Organoindium Reagents: The Preparation and Application in Organic Synthesis

Organoindium Reagents: The Preparation and Application in Organic Synthesis

In search for a pentacoordinated monoorgano stannyl cation

A Xerogel-Sequestered Selenoxide Catalyst for Brominations with Hydrogen Peroxide and Sodium Bromide in an Aqueous Environment

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