Copper‐Catalyzed Multicomponent Coupling of Organoindium Reagents with Nitrogen‐Containing Aromatic Heterocycles

Beveridge, Ramsay E.; Black, D. A.; Arndtsen, Bruce A.

doi:10.1002/ejoc.201000231

Cited by 25 publications

(8 citation statements)

References 64 publications

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“…The same strategy was applied to the functionalization of nitrogen-containing heterocycles by the same group (Scheme 558). 772 Similarly, a selective functionalization of pyridine ring at the 4-position can be achieved when pyridine compounds were treated with triorganoindium reagents and chloroformates in the presence of CuCl. The reactions proceeded in harmony with a range of pyridines incorporated with ketone, cyanide, and aldehyde functionalities.…”

Section: Application In Organic Synthesismentioning

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: Application In Organic Synthesismentioning

confidence: 99%

Organoindium Reagents: The Preparation and Application in Organic Synthesis

et al. 2012

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“…After the successful coupling of the heterocyclic rings, we proceeded with experiments to remove the auxiliary acyl or alkoxycabonyl group and rearomatize the thiazole moiety in 3 . Similar task, although in different context, has been accomplished before by Beveridge et al under oxidative conditions , using o ‐chloranil in acetonitrile at 85°C. Following this literature precedent, and after some experimentation to adjust the reaction conditions, we successfully oxidized compounds 3 with o ‐chloranil and obtained excellent yields of camalexin or benzocamalexin, respectively.…”

Section: Resultsmentioning

confidence: 79%

Synthesis of Camalexin and Related Analogues

Stremski

Statkova-Abeghe

Angelov

et al. 2018

Journal of Heterocyclic Chem

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in Wiley Online Library (wileyonlinelibrary.com).Camalexin is synthesized on a gram scale by coupling of thiazole and indole in an amidoalkylationoxidation sequence. Several high-yielding implementations of this two-step approach are demonstrated with variation of either the intermediate acyliminium reagent or the oxidation conditions. Benzo-analogues and aza-analogues of the natural product are also obtained by this method. As a side result, a new formylation of indole is demonstrated.

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“…Since α‐ketols 12 were obtained in 4–9 % yields in the Reissert‐type acylation of quinolines by Cu I /CH 2 Cl 2 catalytic systems, the acyl Cu species might be involved in these preferred 1,4‐addition reactions. Such a preferential formation of 1,4 adducts has been reported in Reissert‐type transformations of quinolines and pyridines by using organocopper compounds8a–8c or organometallic compounds with Cu I additives 5e,6d,8d,8e. Although details about the solvent effect22 and the role of the cationic Rh I catalyst23 for the regioselectivity remain uncertain at present, the cationic Rh I catalyst might take part in promoting the generation of N ‐acylquinolinium intermediates 13 24…”

Section: Resultsmentioning

confidence: 88%

Reissert‐Type Acylation with Acylzirconocene Chloride Complexes

et al. 2013

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In the presence of ClCO2Et, the use of CuI in MeNO2 efficiently catalyzed the Reissert‐type acylation of isoquinoline derivatives with acylzirconocene chlorides. In the reaction of quinolines with acylzirconocene chlorides, the choice of catalyst and solvent was crucial to the regioselective formation of adducts. The cationic RhI‐catalyzed reaction in MeNO2 preferentially afforded 1,2 adducts. On the other hand, the CuI‐catalyzed reaction in CH2Cl2 preferentially afforded 1,4 adducts.

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Copper‐Catalyzed Multicomponent Coupling of Organoindium Reagents with Nitrogen‐Containing Aromatic Heterocycles

Cited by 25 publications

References 64 publications

Organoindium Reagents: The Preparation and Application in Organic Synthesis

Organoindium Reagents: The Preparation and Application in Organic Synthesis

Synthesis of Camalexin and Related Analogues

Reissert‐Type Acylation with Acylzirconocene Chloride Complexes

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