Generation of Stoichiometric Ethylene and Isotopic Derivatives and Application in Transition‐Metal‐Catalyzed Vinylation and Enyne Metathesis

Min, Geanna K.; Bjerglund, Klaus; Kramer, Steven L.; Gøgsig, Thomas M.; Lindhardt, Anders T.; Skrydstrup, Troels

doi:10.1002/chem.201303668

Cited by 21 publications

(21 citation statements)

References 32 publications

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“…With electron-withdrawing groups on the aromatic ring, acyldiallylamines 1gg-oo also gave good results in the RCM/dehydrogenation tandem reaction under the standard conditions, to generate N-acylpyrroles 2gg-oo in good yields (entries 7-15). Furanyl-and thiophenyl-containing diallylamines 1pptt were also found to be suitable substrates for the RCM/dehydrogenation tandem reaction, providing the corresponding N-acylpyrroles 2pp-tt in excellent yields (entries [16][17][18][19][20]. Notably, this protocol is also suitable for the N-alkylsubstituted substrates 1uu and 1vv, which could be converted into pyrroles 2uu and 2vv in 80% and 82% yield, respectively (entries 21 and 22).…”

Section: Syn Thesismentioning

confidence: 94%

Synthesis of N-Sulfonyl- and N-Acylpyrroles via a Ring-Closing Metathesis/Dehydrogenation Tandem Reaction

et al. 2019

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N-Sulfonyl- and N-acylpyrroles were synthesized via olefin ring-closing metathesis of diallylamines and in situ oxidative aromatization in the presence of the ruthenium Grubbs catalyst and a suitable copper catalyst. In the presence of Cu(OTf)2 and CuBr2, the reaction afforded N-sulfonyl- and N-acylpyrroles, respectively, in one pot. Under an oxygen atmosphere, the reaction went smoothly without the need of hydroperoxide oxidants. This protocol possesses many advantages, such as using a nonhazardous oxidant and readily available starting materials, operating in one pot, and showing a broad substrate scope.

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Section: Syn Thesismentioning

confidence: 94%

Synthesis of N-Sulfonyl- and N-Acylpyrroles via a Ring-Closing Metathesis/Dehydrogenation Tandem Reaction

et al. 2019

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“…Our search for a thiol precursor ultimately led us to the commercially available and inexpensive S ‐methylisothiourea hemisulfate salt (Scheme b), which upon treatment with equimolar amounts of NaOH produces methanethiol. We envisioned that the two‐chamber system, previously used for the ex situ generation of carbon monoxide, dihydrogen, ethylene, and hydrogen cyanide, could be exploited for the ex situ delivery of MeSH.…”

Section: Methodsmentioning

confidence: 99%

Ex Situ Formation of Methanethiol: Application in the Gold(I)‐Promoted Anti‐Markovnikov Hydrothiolation of Olefins

et al. 2018

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A protocol for the Au-promoted anti-Markovnikov hydrothiolation of olefins using ex situ generated methanethiol is reported. The use of S-methylisothiourea hemisulfate salt as a solid precursor for methanethiol generation ensures a safe and reliable deliverance of a stoichiometric amount of this thiol. The procedure was shown to work for a broad range of olefins providing the corresponding hydrothiolated adduct in good to excellent yields. Mechanistic evaluations suggest that thiyl radicals are generated and that gold acts as an efficient but stable radical initiator.

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“…The synthesis of the common intermediate 13 commenced with a modified Van Leusen oxazole synthesis on the previously reported aldehyde 15 ( Scheme 2 ) [ 9 ].…”

Section: Resultsmentioning

confidence: 99%

Total Synthesis of Phorbazole B

et al. 2020

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Phorbazoles are polychlorinated heterocyclic secondary metabolites isolated from a marine sponge and several of these natural products have shown inhibitory activity against cancer cells. In this work, a synthesis of the trichlorinated phorbazole B using late stage electrophilic chlorination was developed. The synthesis relied on the use of an oxazole precursor, which was protected with an iodine in the reactive 4-position, followed by complete chlorination of all pyrrole positions. Attempts to prepare phorbazole A and C, which contain a 3,4-dichlorinated pyrrole, were unsuccessful as the desired chlorination pattern on the pyrrole could not be obtained. The identities of the dichlorinated intermediates and products were determined using NMR techniques including NOESY/ROESY, 1,1-ADEQUATE and high-resolution CLIP-HSQMBC.

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Generation of Stoichiometric Ethylene and Isotopic Derivatives and Application in Transition‐Metal‐Catalyzed Vinylation and Enyne Metathesis

Abstract: Scheme 3. Ni-catalyzed vinylation of aryl triflates. Scheme 4. Ni-catalyzed vinylation of benzylic chlorides. Scheme 5. Ru-catalyzed enyne metathesis of alkynes with ethylene.

Cited by 21 publications

References 32 publications

Synthesis of N-Sulfonyl- and N-Acylpyrroles via a Ring-Closing Metathesis/Dehydrogenation Tandem Reaction

Synthesis of N-Sulfonyl- and N-Acylpyrroles via a Ring-Closing Metathesis/Dehydrogenation Tandem Reaction

Ex Situ Formation of Methanethiol: Application in the Gold(I)‐Promoted Anti‐Markovnikov Hydrothiolation of Olefins

Total Synthesis of Phorbazole B

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