Intermolecular Addition of Glycosyl Halides to Alkenes Mediated by Visible Light

Andrews, Robert S.; Becker, Jennifer J.; Gagné, Michel R.

doi:10.1002/ange.201004311

Cited by 86 publications

(8 citation statements)

References 45 publications

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“…[6] In parallel with other groups’ efforts in this field, [7–11] we [12] have been engaged in exploring new reactivities of nitrogen radical cations generated via direct oxidation of the corresponding amines by photoexcited ruthenium polypyridyl complexes [13] . Although this type of oxidation was first discovered in the late 1970s, [14] its potential in organic synthesis has not been extensively explored until recently.…”

mentioning

confidence: 99%

A Visible‐Light‐Mediated Oxidative CN Bond Formation/Aromatization Cascade: Photocatalytic Preparation of N‐Arylindoles

Maity¹,

Zheng²

2012

Angew Chem Int Ed

247

104

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Indoles: A joint effort of light and air We have developed a mild aerobic oxidation protocol using visible light photocatalysis to synthesize structurally diverse N-arylindoles. The procedure employs 4 mol% [Ru(bpz)3](PF6)2, 18W LED light, and is performed open to the atmosphere. Readily prepared o-stryryl anilines are converted to a variety of indoles via a cascade sequence composed of oxidation of anilines, C-N bond formation, and aromatization. A 1,2-carbon shift can be also incorporated into this cascade event to further extend the substrate scope of the method. bpz = 2, 2′-Bipyrazine

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mentioning

confidence: 99%

A Visible‐Light‐Mediated Oxidative CN Bond Formation/Aromatization Cascade: Photocatalytic Preparation of N‐Arylindoles

Maity¹,

Zheng²

2012

Angew Chem Int Ed

247

104

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“…Further syntheses of conjugates with fatty acids and with a carbohydrate using other strategies are described in Refs. [8][9][10].…”

Section: Resultsmentioning

confidence: 99%

“…This way with the O-nucleophiles: methanol, phenols, carbohydrates, a-tocopherol, and estradiol the corresponding substitution products were obtained as mixture of regioisomers ( Table 2, Nr. [1][2][3][4][5][6][7][8][9][10][11][12]. With the N-nucleophiles: picolylamine and piperidine, and the C-nucleophiles: dimethyl malonate, nitromethane, methyl acetoacetate, and malodinitrile the corresponding Pd(0)catalyzed C-N-and C-C-bond formations could be achieved ( Table 2, Nr.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of fatty acid conjugates with phenols, carbohydrates, amines, and CH‐acidic compounds by Pd(0)‐catalyzed allylic substitution

Zobel

Schäfer

2016

Euro J Lipid Sci & Tech

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The efficiency of a pharmaceutical can be increased by connecting it to a fatty acid. Nucleophilic allylic substitution of methyl 10‐undecenoate and methyl oleate with palladium(0) as catalyst is explored to see, whether this reaction is useful for such connections with regard to yield and selectivity. For that purpose the allylic CH‐bonds in methyl 10‐undecenoate and methyl oleate were oxidized with selenium dioxide and tert‐butylhydroperoxide. The obtained allylic alcohols were then activated by conversion into their methyl carbonates. Allylic substitution was performed with O‐nucleophiles as methanol, carbohydrates, and different phenols as α‐tocopherol and estradiol; furthermore N‐ and C‐nucleophiles were applied. The yields of substitution products were in the range of 37–98%. High yields of conjugates were obtained with phenols, even when the hydroxy group was sterically shielded. These conjugates have an ether bond, a CN or a CC bond as link. They should have the advantage to be more stable in body fluids than the frequently applied conjugates being connected by the less inert ester bond. Triesters and dicyanoesters obtained with C‐nucleophiles can be possibly used as cross linkers for polyesters and polyamides. Practical applications: These conjugates should be more stable in cells and body fluids than the frequently applied conjugates being connected by the less inert ester bond. Triesters and dicyanoesters obtained with C‐nucleophiles can be possibly used as cross linkers for polyesters and polyamides. Methyl 9‐hydroxy‐10‐undecenoate is prepared by allylic oxidation from methyl 10‐undecenoate. After esterification to the methyl carbonate this leaving group is substituted via Pd(0)‐catalysis by O‐, N‐, and C‐nucleophiles to afford fatty acid conjugates. Similarly methyl oleate is converted.

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“…[4] Stephenson und Mitarbeiter haben sich kürzlich mit diesen Prozessen nochmals beschäftigt (Schema 1). Mit der präparativen Weiterverwendung der durch reduktive, photoredoxkatalysierte Spaltung der C-X-Bindung erzeugten Radikale befassten sich außerdem die Gruppen von Stephenson, [7] GagnØ, [8] Reiser, [9] Masson [10] und Yu. Mit der präparativen Weiterverwendung der durch reduktive, photoredoxkatalysierte Spaltung der C-X-Bindung erzeugten Radikale befassten sich außerdem die Gruppen von Stephenson, [7] GagnØ, [8] Reiser, [9] Masson [10] und Yu.…”

Section: Lichtkatalysierte Radikalische Additionen Und Cycloadditionenunclassified

Photoredoxkatalyse mit sichtbarem Licht

2012

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Organische Umsetzungen, die durch sichtbares Licht ausgelöst werden, finden seit einigen Jahren immer größere Aufmerksamkeit. Insbesondere im Hinblick auf Kosten, Sicherheit, Verfügbarkeit und Umweltfreundlichkeit ist die Entwicklung solcher photokatalytischer Reaktionen zur effizienten Herstellung von Feinchemikalien höchst wünschenswert. In diesem Kurzaufsatz werden die jüngsten Fortschritte auf diesem sich schnell entwickelnden Forschungsgebiet erörtert.

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Intermolecular Addition of Glycosyl Halides to Alkenes Mediated by Visible Light

Cited by 86 publications

References 45 publications

A Visible‐Light‐Mediated Oxidative CN Bond Formation/Aromatization Cascade: Photocatalytic Preparation of N‐Arylindoles

A Visible‐Light‐Mediated Oxidative CN Bond Formation/Aromatization Cascade: Photocatalytic Preparation of N‐Arylindoles

Synthesis of fatty acid conjugates with phenols, carbohydrates, amines, and CH‐acidic compounds by Pd(0)‐catalyzed allylic substitution

Photoredoxkatalyse mit sichtbarem Licht

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