Palladium-catalyzed cross-coupling reaction of sulfoxonium ylides and benzyl bromides by carbene migratory insertion

Yan, Kaichuan; He, Maoyao; Li, Jianglian; He, Hua; Lai, Ruizhi; Luo, Yi; Guo, Li; Wu, Yong

doi:10.1039/d0cc06236g

Cited by 9 publications

(5 citation statements)

References 71 publications

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“…4 To date, various strategies have emerged to realize this reaction. For example, transition-metal catalysis, 5 organocatalysis, 6 heterogeneous catalysis, 7 biocatalysis, 8 and photocatalysis 9 have proven useful in the context of this reaction (Scheme 1 ). Although they represent significant achievements, these procedures typically not only require elaborately selected catalysts but also diazo compounds.…”

Section: Table 1 Optimization Of the S–h Insertion Reac...mentioning

confidence: 99%

A New Approach to the S–H Insertion Reaction of α-Keto Esters and Thiols

Yuan¹,

Fang²,

Tian³

et al. 2023

Synlett

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Sulfur-containing compounds are well known for their frequent occurrence in a large number of natural and synthetic molecules with relevant biological activity. An easy and highly efficient approach to sulfur-containing compounds, by S–H insertion reactions of α-keto esters with thiols, is reported. The substrate scope was remarkably wide, affording the corresponding products in up to 97% yield. Overall, the raw materials were readily available and the reaction conditions were mild in this synthetic method.

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Section: Table 1 Optimization Of the S–h Insertion Reac...mentioning

confidence: 99%

A New Approach to the S–H Insertion Reaction of α-Keto Esters and Thiols

Yuan¹,

Fang²,

Tian³

et al. 2023

Synlett

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“…13 20 The following preparation of ethyl 2-(diethoxyphosphoryl)-3-phenylpropanoate is representative. To a solution of triethyl phosphonoacetate (500 mg, 2.23 mmol, 1.0 equiv) in dry THF (7.4 mL, 0.3 M) was added NaH (107 mg, 2.68 mmol, 60% dispersion in mineral oil, 1.2 equiv) at 0 °C, and the reaction was Ethyl 21 Following the general procedure B, the reaction of 2-cyanobenzaldehyde (262 mg) afforded (Z)-8c as a colorless oil (53 mg, 10%). R f = 0.55 [EtOAc/hexanes, 1:5 (v/v)].…”

Section: Ethyl (E)-2-(3-bromobenzyl)-3-(2-cyanophenyl)acrylate [(E)-8l]mentioning

confidence: 99%

Insight into Stereocontrol in the Asymmetric Intramolecular Allylation with a tert-Butylsulfinamide Nucleophile: Application in the Synthesis of Chiral Isoindoline-1-Carboxylic Acid Esters

Hung

Chou

et al. 2022

J. Org. Chem.

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The asymmetric induction afforded by a chiral sulfinyl group in a palladium/Brønsted-acid-catalyzed intramolecular allylic amination was investigated. Predictions of the diastereoselectivity for various substrates under assumed total thermodynamic control were obtained from density functional theory (DFT), and the correlation with experimental data demonstrates abrupt changes to kinetic control across the substrate scope. The resulting heterocyclic product was readily converted to valuable isoindoline-1-carboxylic acid esters by a two-step oxidation sequence, providing asymmetric access to a key unnatural α-amino acid scaffold.

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“…Recently, sulfoxonium ylides as viable alternatives for diazo compounds have been made rapid development in the chemical field. Our group has done a lot of preliminary studies on sulfoxonium ylides, [4,8] such as Pd‐catalyzed cross‐coupling reaction, [4b] C−H activation, [8b] cyclic synthesis of 2‐aminothiazoles, [8d] N−H, [8c] S−H, [8a] B−H insertion, [4a] etc. In addition, many reactions, [9] such as insertions (N, S, O, P, B−H insertion), [9a–e] cyclization reactions, [9f] C−H activation, [9g,h] have been reported by different groups as well.…”

Section: Introductionmentioning

confidence: 99%

Sulfoxonium Ylides as Carbene Precursors in Rhodium‐Catalyzed Sommelet‐Hauser Rearrangement for the Synthesis of S/Se‐Containing Compounds

Luo,

Lin,

Hao

et al. 2023

Eur J Org Chem

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Rhodium‐catalyzed Sommelet‐Hauser rearrangement derived from α‐thioesters/α‐selenoesters and sulfoxonium ylides has been developed for the synthesis of various sulfur/selenium‐containing ortho‐substituted aromatic compounds in medium to excellent yields (39 examples; up to 97 %). Sulfoxonium ylides as the safe carbene precursors are firstly used in Sommelet‐Hauser rearrangement reactions, which is superior to traditional diazo compounds. The present reaction has the advantages of mild condition, safety and broad substrate scope, which afford a unique method for the synthesis of sulfur/selenium‐containing compounds with a tertiary carbon center.

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Palladium-catalyzed cross-coupling reaction of sulfoxonium ylides and benzyl bromides by carbene migratory insertion

Abstract: A palladium-catalyzed cross-coupling reaction of sulfoxonium ylides and benzyl bromides has been developed, which has the potential safety advantages over previous carbene coupling reactions using either diazo compounds or their...

Cited by 9 publications

References 71 publications

A New Approach to the S–H Insertion Reaction of α-Keto Esters and Thiols

A New Approach to the S–H Insertion Reaction of α-Keto Esters and Thiols

Insight into Stereocontrol in the Asymmetric Intramolecular Allylation with a tert-Butylsulfinamide Nucleophile: Application in the Synthesis of Chiral Isoindoline-1-Carboxylic Acid Esters

Sulfoxonium Ylides as Carbene Precursors in Rhodium‐Catalyzed Sommelet‐Hauser Rearrangement for the Synthesis of S/Se‐Containing Compounds

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