Palladium-catalyzed synthesis of 2-substituted indoles

Rudisill, Duane E.; Stille, J. K.

doi:10.1021/jo00286a014

Cited by 168 publications

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“…The latter is often accomplished by coupling more traditional palladium-catalyzed coupling chemistry with cyclization, and provides an avenue to readily expand the diversity of indole products available. As illustrated with the examples in Scheme 6.5, this can be done via the Sonogashira coupling of 2 with R-X [5] coupling of 3 with alkynylstannanes [6], or the Sonogashira coupling of 4 with terminal alkynes [7]. Each of these generate the analogous ortho-alkynylaniline derivatives for cyclization.…”

Section: Addition To Alkynesmentioning

confidence: 99%

“…This will focus on routes that directly assemble the aromatic heterocyclic core, rather than their subsequent functionalization or the use of palladium to assemble precursors for traditional cyclocondensations, and on processes that involve generation of carbonheteroatom bonds. 6.2 Palladium p-Lewis Acidity: Intramolecular Nucleophilic Attack on Unsaturated Bonds…”

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confidence: 99%

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The Palladium‐Catalyzed Synthesis of Aromatic Heterocycles

Arndtsen

2010

Catalyzed Carbon‐Heteroatom Bond Formation

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Section: Addition To Alkynesmentioning

confidence: 99%

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confidence: 99%

The Palladium‐Catalyzed Synthesis of Aromatic Heterocycles

Arndtsen

2010

Catalyzed Carbon‐Heteroatom Bond Formation

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“…Eventually we achieved some measure of success employing the reagent system PdCl 2 (MeCN) 2 /NaOAc, which afforded 60-70% yields of the desired enamide 82b. 24,25 However, by far the most useful procedure was discovered serendipitously upon attempted cleavage of the TMS group from alkyne hydrazide 81a (Y = TMS). This material was obtained from adduct 80 by hydrolysis and amidation under carefully controlled conditions.…”

Section: The Sigmatropic Rearrangement Strategy: First Successmentioning

confidence: 99%

Synthetic Studies in Phytochrome Chemistry

Jacobi

Odeh²,

Buddhu³

et al. 2005

Synlett

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An account is given of the author's several approaches to the synthesis of the parent chromophore of phytochrome (1), a protein-bound linear tetrapyrrole derivative that controls photomorphogenesis in higher plants. These studies culminated in enantioselective syntheses of both 2R-and 2S-phytochromobilin (4), as well as several 13 C-labeled derivatives designed to probe the site of Z,Eisomerization during photoexcitation. When reacted in vitro, synthetic 2R-4 and recombinant-derived phytochrome apoprotein N-C produced a protein-bound chromophore with identical difference spectra to naturally occurring 1.

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“…Synthesis of ethynylated Pcs 1 a, 1 b, 2 a and 2 b: The conversions of 3 and 4 into the ethynylated compounds were investigated by using both the Sonogashira coupling method, [23] which led to the TMS-protected derivatives 1 a and 2 a (TMS trimethylsilyl), and the Stille procedure, [24] which led directly to the unprotected compounds 1 b and 2 b.…”

Section: Introductionmentioning

confidence: 99%

Phthalocyaninodehydroannulenes

Cook

Heeney

2000

Chem. Eur. J.

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4-Bromo- and 4,5-dibromo-3,6-dibutoxyphthalonitrile have been prepared and treated with 3,6-didecylphthalonitrile in cross tetramerisation reactions in the presence of nickel acetate to afford monobromo- and dibromo-dibutoxyhexadecylphthalocyaninato nickel(II) complexes. Sonogashira and Stille coupling reactions on these compounds displaced the bromine substituents by ethynyl groups. Oxidative coupling of the monoethynyl derivatised nickel phthalocyanine afforded a butadiynyl-linked dinuclear phthalocyanine. The corresponding coupling reaction of the diethynylated phthalocyanine gave a mixture of phthalocyaninodehydroannulenes. Separation of the mixture yielded the diphthalocyaninodehydro[12]annulene as the major product. Electrospray mass spectrometry provides evidence for its aggregation in solution. The corresponding cyclic trimer, the triphthalocyaninodehydro[18]annulene, has been identified as a minor product. Both compounds show a large splitting of the Q-band absorption in the visible region spectrum. Most of the mononuclear phthalocyanine precursors exhibit discotic liquid crystal behaviour. The diphthalocyaninodehydro[12]annulene also enters a mobile phase on heating, but undergoes an irreversible change at 220 degrees C. MALDI-TOF mass spectrometry of the product reveals that the compound undergoes oligomerisation at this temperature.

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Palladium-catalyzed synthesis of 2-substituted indoles

Cited by 168 publications

References 0 publications

The Palladium‐Catalyzed Synthesis of Aromatic Heterocycles

The Palladium‐Catalyzed Synthesis of Aromatic Heterocycles

Synthetic Studies in Phytochrome Chemistry

Phthalocyaninodehydroannulenes

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