New Synthetic reactions. Alkylative elimination

Trost, Barry M.; CONWAY, W. PAUL; Strege, Paul E.; Dietsche, Thomas J.

doi:10.1021/ja00829a089

Cited by 44 publications

(14 citation statements)

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“…The configuration of the diene was confirmed by 1 H NMR (Supplementary Materials: Figure S1). The chemical shift of the hydrogen alpha to the ester moiety is in accordance with the values reported in the literature for a (E/Z)-diene, around 5.5 ppm (vs. 6.0 ppm for a E/E fragment) [58].…”

Section: Substrate Scopesupporting

confidence: 90%

Solvent-Free Mizoroki-Heck Reaction Applied to the Synthesis of Abscisic Acid and Some Derivatives

2018

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Abscisic acid (ABA) is a natural product, which is a well-known phytohormone. However, this molecule has recently exhibited interesting biological activities, emphasizing the need for a simple and direct access to new analogues based on the ABA framework. Our strategy relies on a pallado-catalyzed Mizoroki-Heck cross-coupling as key reaction performed in solvent and ligand free conditions. After a careful optimization, we succeeded in accessing various (E/Z)-dienes and (E/E/Z)-trienes in moderate to good yields without isomerization and applied the same approach to the synthesis of ABA in an environmentally sound manner.

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Section: Substrate Scopesupporting

confidence: 90%

Solvent-Free Mizoroki-Heck Reaction Applied to the Synthesis of Abscisic Acid and Some Derivatives

2018

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“…1978, 100, 920-925. (11) (a) For simplicity we will generally use kcal to indicate kcal/mol. (b) Comparing the calculated energies for the processes (I) and (II) leads to an energy difference of 28.5 kcal.…”

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confidence: 99%

A palladium-catalyzed reaction of a .pi.-allyl ligand with a nucleophile. An MO study about a feature of the reaction and a ligand effect on the reactivity

Sakaki¹,

Nishikawa²,

Ohyoshi³

1980

J. Am. Chem. Soc.

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A CNDO-type MO study was carried out for the reaction between OH-and the x-allyl ligand coordinating to palladium(ll), as a model reaction of various nucleophilic attacks on the x-allyl ligand. MO calculations showed the following feature of the reaction: when a nucleophile, Y, approaches the n-allyl ligand, the palladium(l1) is reduced to palladium(O), and the n-allyl ligand is eliminated as an allyl derivative, CHz=CHCHzY, from the palladium(0). This feature agrees with the experimental result. The reactivity regarding the OH-nucleophilic attack increases i n the order PdClz(x-C3H~)-<<

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“…Thioethers are versatile synthetic intermediates, as they are readily oxidized to either the sulfoxide or the sulfone . Sulfoxides are well-known for enabling syn eliminations, Mislow–Evans rearrangements, , Pummerer reactions, , and sulfoxide–metal exchanges , while also acting as a useful ligand class for transition metal catalysis . The higher-oxidation state sulfones also provide ample opportunities in organic synthesis, most notably as alkene precursors in the Julia–Lythgoe olefination, , Kocienski-modified Julia olefination, , and Ramberg–Bäcklund rearrangement. , A recent report has also highlighted the utility of sulfones as radical cross-coupling partners .…”

Section: Introductionmentioning

confidence: 99%

Fenton-Inspired C–H Functionalization: Peroxide-Directed C–H Thioetherification

2019

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Substoichiometric iron mediates the thioetherification of unactivated aliphatic C−H bonds directed by resident silylperoxides. Upon exposure to a catalytic amount of iron(II) triflate, TIPS-protected peroxides bearing primary, secondary, and tertiary C−H sites undergo chemoselective thioetherification of remote C−H bonds with diaryl disulfides. The reaction demonstrates a broad substrate scope and functional group tolerance without the use of any noble metal additives. Mechanistic experiments suggest that the reaction proceeds through 1,5-H atom abstraction by a hydroxyl radical generated with iron.

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New Synthetic reactions. Alkylative elimination

Cited by 44 publications

References 0 publications

Solvent-Free Mizoroki-Heck Reaction Applied to the Synthesis of Abscisic Acid and Some Derivatives

Solvent-Free Mizoroki-Heck Reaction Applied to the Synthesis of Abscisic Acid and Some Derivatives

A palladium-catalyzed reaction of a .pi.-allyl ligand with a nucleophile. An MO study about a feature of the reaction and a ligand effect on the reactivity

Fenton-Inspired C–H Functionalization: Peroxide-Directed C–H Thioetherification

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