Mild Chemical and Biological Synthesis of Donor–Acceptor Flanked Reporter Stilbenes: Demonstration of a Physiological Wittig Olefination Reaction

McLeod, David; McNulty, James

doi:10.1002/ejoc.201201042

Cited by 13 publications

(8 citation statements)

References 71 publications

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“…This was prepared according to the general procedure, and the title compound was isolated as a pale yellow solid (93% yield). Spectral data obtained were in good agreement with those reported in the literature …”

Section: Methodssupporting

confidence: 89%

Palladium-Catalyzed, ortho-Selective C–H Halogenation of Benzyl Nitriles, Aryl Weinreb Amides, and Anilides

Das

Kapur

2017

J. Org. Chem.

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A palladium-catalyzed, ortho-selective C-H halogenation methodology is reported herein. The highlight of the work is the highly selective C(sp)-H functionalization of benzyl nitriles in the presence of activated C(sp)-H bond, which results in good yields of the halogenated products with excellent regioselectivity. Along with benzyl nitriles, aryl Weinreb amides and anilides have been evaluated for the transformation using aprotic conditions. Mechanistic studies yield interesting aspects with respect to the pathway of the reaction and the directing group abilities.

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Section: Methodssupporting

confidence: 89%

Palladium-Catalyzed, ortho-Selective C–H Halogenation of Benzyl Nitriles, Aryl Weinreb Amides, and Anilides

Das

Kapur

2017

J. Org. Chem.

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“…N-Methyl-N-(p-tolyl)acetamide (3b). 31 146.9 mg, 90% yield. Isolated by flash column chromatography (ethyl acetate/petroleum ether = 1:2, R f = 0.3).…”

Section: ■ Experimental Sectionmentioning

confidence: 99%

Amide Bond Formation through Iron-Catalyzed Oxidative Amidation of Tertiary Amines with Anhydrides

Fan

2013

J. Org. Chem.

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A general and efficient method for amide bond synthesis has been developed. The method allows for synthesis of tertiary amides from readily available tertiary amines and anhydrides in the presence of FeCl2 as catalyst and tert-butyl hydroperoxide in water (T-Hydro) as oxidant. Mechanistic studies indicated that the in situ-generated α-amino peroxide of tertiary amine and iminium ion act as key intermediates in this oxidative transformation.

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“…All manipulations involving air-sensitive reagents were performed under a dry nitrogen atmosphere. 1-Methyl-2-phenyl-1Hbenzimidazole (LG0), 57 4-(diphenylamino)benzaldehyde (2), 58 4-[bis [4-(diphenylamino)phenyl] amino]benzaldehyde (5), 59 and 4-[bis[4-(9H-carbazol-9-yl)phenyl]amino]benzaldehyde (6) 59 were prepared according to literature procedures.…”

Section: Methodsmentioning

confidence: 99%

Self-host homoleptic green iridium dendrimers based on diphenylamine dendrons for highly efficient single-layer PhOLEDs

Tian

Song

et al. 2014

J. Mater. Chem. C

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Mild Chemical and Biological Synthesis of Donor–Acceptor Flanked Reporter Stilbenes: Demonstration of a Physiological Wittig Olefination Reaction

Abstract: Unprecedented chemoselectivity is reported for the Wittig olefination reaction leading to the formation of reporter stilbenes under physiological conditions.

Cited by 13 publications

References 71 publications

Palladium-Catalyzed, ortho-Selective C–H Halogenation of Benzyl Nitriles, Aryl Weinreb Amides, and Anilides

Palladium-Catalyzed, ortho-Selective C–H Halogenation of Benzyl Nitriles, Aryl Weinreb Amides, and Anilides

Amide Bond Formation through Iron-Catalyzed Oxidative Amidation of Tertiary Amines with Anhydrides

Self-host homoleptic green iridium dendrimers based on diphenylamine dendrons for highly efficient single-layer PhOLEDs

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