2,3-Dichloro-5,6-dicyano-1,4-benzo-quinone

Buckle, Derek R.; Collier, S. J.; McLaws, Mark D.

doi:10.1002/047084289x.rd114

Cited by 5 publications

(1 citation statement)

References 146 publications

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“…Both primary and secondary thiols are reactive under these conditions. However, DDQ’s strong oxidative properties and moisture sensitivity might narrow its applicability due to its low compatibility with functional groups and the risk of releasing highly toxic HCN when it reacts with water . Overall, while desulfurization has received considerable interest, the focus has predominantly been on hydrodesulfurization, leaving other reactions largely unexplored.…”

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confidence: 99%

Desulfurization of Thiols for Nucleophilic Substitution

Fu,

Lin,

Xiao

2024

Org. Lett.

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Although the desulfurization of thiols is a topic of great importance and has received significant attention, most efforts have focused on the hydrodesulfurization of thiols. In this work, we describe the desulfurization of thiols for nucleophilic substitution. This process occurs rapidly, promoted by the Ph 3 P/ICH 2 CH 2 I system, and can be extended to a wide range of nucleophiles. Notably, free amines can be employed as nucleophiles to synthesize various secondary and tertiary amines. This method tolerates a wide array of functional groups, including hydroxyl groups in amination reactions. Benzyl thiols are particularly reactive and can be completely converted at room temperature within 15 min. Although alkyl thiols show lower reactivity, they can also be converted smoothly at a reaction temperature of 70 °C overnight.

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confidence: 99%

Desulfurization of Thiols for Nucleophilic Substitution

Fu,

Lin,

Xiao

2024

Org. Lett.

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Multistep Transformations of BIS‐Thioenol Ether‐Containing Chiral Building Blocks: New Avenues in Glycochemistry

D’Alonzo¹,

Palumbo²,

Guaragna³

2016

Domino and Intramolecular Rearrangement Reactions as Advanced Synthetic Methods in Glycoscience

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Asymmetric Oxidative Mannich Reactions

et al. 2020

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The asymmetric Mannich reaction is one of the most straightforward methodologies for the enantioselective synthesis of chiral amines. In general, asymmetric Mannich reactions involve the use of imines as electrophiles. However, in recent years, several asymmetric oxidative Mannich reactions have been reported using amines as electrophiles. This review provides an overview of these recent publications, including the different oxidants used and the scope and limitations of the different catalytic systems.

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2,3-Dichloro-5,6-dicyano-1,4-benzo-quinone

Cited by 5 publications

References 146 publications

Desulfurization of Thiols for Nucleophilic Substitution

Desulfurization of Thiols for Nucleophilic Substitution

Multistep Transformations of BIS‐Thioenol Ether‐Containing Chiral Building Blocks: New Avenues in Glycochemistry

Asymmetric Oxidative Mannich Reactions

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