Indium-mediated Allylation of Heteroaryl, Benzyl, and Cinnamyl Thiocyanates: A Novel Route for 3-(Allylsulfanyl)-1<i>H</i>-indoles

Yadav, J. S.; Reddy, B. V. Subba; Chandrakanth, D.; Gopal, A. V. Hara

doi:10.1246/cl.2008.1082

Cited by 9 publications

(4 citation statements)

References 24 publications

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Section: Allylindium Reagentsmentioning

confidence: 99%

“…Finally, like the allylation reaction, the indium-mediated propargylation and allenylation of electrophiles, such as 1,2-dicarbonyl compounds, ,,, β-chloro vinylaldehyde, acetal and ketal, phenacyl bromide, α-diazoketone, glycal, α-imino ethyl ester, imino isatin, epoxide, quinolinium and isoquinolinium salts, , organosilyl chloride, thiocyanate, hydroxyphthalide, and others, have also been reported.…”

Section: Propargylindium and Allenylindium Reagentmentioning

confidence: 99%

“…In addition, like the allylation reaction, several cases of the indium-mediated benzylation of electrophiles, such as 1,2-diketone, ninhydrin and alloxan, β,γ-unsaturated α-methoxy- N -methoxycarbonylpiperidine, α,β-unsaturated nitrile, and thiocyanate, have also been reported.…”

Section: Benzylindium Reagentmentioning

confidence: 99%

“…A high-yielding preparation of 3-(allylsulfanyl)indoles by means of an indium-mediated allylation of 3-thiocyanatoindoles was described by Yadav and co-workers (Scheme 334). 533 Other organohalides such as propargyl bromide, benzyl bromide, and n-butyl bromide are also amenable to the mild reaction conditions. Zhang of unsymmetrical diallylsulfides in reasonable yields via an indium-mediated one-pot coupling of Baylis−Hillman acetates, sodium thiosulfate, and allyl bromide (Scheme 335).…”

Section: Addition To Miscellaneous Electrophilesmentioning

confidence: 99%

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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: Allylindium Reagentsmentioning

confidence: 99%

Section: Propargylindium and Allenylindium Reagentmentioning

confidence: 99%

Section: Benzylindium Reagentmentioning

confidence: 99%

Section: Addition To Miscellaneous Electrophilesmentioning

confidence: 99%

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Organoindium Reagents: The Preparation and Application in Organic Synthesis

et al. 2012

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ChemInform Abstract: Indium‐Mediated Allylation of Heteroaryl, Benzyl, and Cinnamyl Thiocyanates: A Novel Route for 3‐(Allylsulfanyl)‐1H‐indoles.

et al. 2009

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N‐Iodosuccinimide Catalyzed Oxidative Selenocyanation and Thiocyanation of Electron Rich Arenes

2016

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Selenocyanation and thiocyanation of electron rich arenes have been achieved using N‐iodosuccinimide (NIS) as a catalyst and aq. tert‐butyl hydroperoxide (TBHP) as an oxidant at room temperature. This method works efficiently for indoles, anilines, phenols, and other electron‐rich arene systems to furnish the products in good to excellent yields and exhibits a good regioselectivity. The products synthesized are further used to prepare their corresponding trifluoromethyl derivatives using reported reactions.

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Indium-mediated Allylation of Heteroaryl, Benzyl, and Cinnamyl Thiocyanates: A Novel Route for 3-(Allylsulfanyl)-1H-indoles

Abstract: Heteroaryl, benzyl, and cinnamyl thiocyanates undergo smooth allylation with allyl bromide in the presence of indium or zinc metal in THF at room temperature to produce the corresponding allyl sulfides in good yields and with high selectivity.

Cited by 9 publications

References 24 publications

Organoindium Reagents: The Preparation and Application in Organic Synthesis

Organoindium Reagents: The Preparation and Application in Organic Synthesis

ChemInform Abstract: Indium‐Mediated Allylation of Heteroaryl, Benzyl, and Cinnamyl Thiocyanates: A Novel Route for 3‐(Allylsulfanyl)‐1H‐indoles.

N‐Iodosuccinimide Catalyzed Oxidative Selenocyanation and Thiocyanation of Electron Rich Arenes

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