Selectivity control in thiol–yne click reactions <i>via</i> visible light induced associative electron upconversion

Burykina, Julia V.; Shlapakov, Nikita S.; Gordeev, Evgeniy G.; König, Burkhard; Ananikov, Valentine P.

doi:10.1039/d0sc01939a

Cited by 61 publications

(42 citation statements)

References 47 publications

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“…It is important to point out that the observed signals of 3a corresponded to [M + H] + ( m/z 239.1576) and less typical [M − H] + ( m/z 237.1420) ions ( Figure S3, Supplementary Materials ). Formation of [M − H] + ions was earlier observed by our group for vinylsulfides and monoselenide-substituted-1,3-dienes [ 25 , 37 ]. Here and further, the most intensive signals (more often [M − H] + ) are described.…”

Section: Resultsmentioning

confidence: 76%

“…The target substrates are thiols and the products of their interaction with alkynes-vinyl sulfides. This process usually occurs via radical, nucleophilic, or catalytic pathways [23][24][25][26]. Today, systems based on Cu-, Ni-, or Pd-complexes find wide application in the hydrothiolation process [27][28][29][30] as well as other reactions of C-S bond formation [31][32][33][34].…”

Section: Introductionmentioning

confidence: 99%

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ESI-MS Analysis of Thiol-yne Click Reaction in Petroleum Medium

2021

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Petroleum contains a large number of heteroatomic compounds, but today, most of them are not efficiently utilized. The constant development of the sustainability concept recalls for rethinking the usage of fossil resources with improved chemical utility. In order to initiate research aimed at involving active petroleum compounds in chemical transformations, a new analytical method for product detection is needed. Here, we study the click reaction of thiols with alkynes, leading to the formation of α-vinyl sulfides directly in the petroleum environment. The reaction was carried out using an (IMes)Pd(acac)Cl catalyst, which demonstrated tolerance to petroleum components. In this study, the concentration of thiols ranged from 1 M to 0.01 M (from 8% to 0.1%). To detect products at low concentrations, a special alkyne labeled with an imidazole moiety was used. This approach made it possible to observe the formation of vinyl sulfides by electrospray ionization mass spectrometry (ESI-MS), which provides an opportunity for further optimization of the reaction conditions and future developments for the direct involvement of oil components in chemical reactions.

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Section: Resultsmentioning

confidence: 76%

Section: Introductionmentioning

confidence: 99%

ESI-MS Analysis of Thiol-yne Click Reaction in Petroleum Medium

2021

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“…An associative electron upconversion was proposed to be a key step determining the selectivity of thiol-yne reaction by Ananikov’s group [ 62 ]. They developed a transition-metal-free photoredox catalytic system for the selective synthesis of four types of vinyl sulfides, including the challenging Markovnikov-type products.…”

Section: Photoredox Catalytic Markovnikov-selective Thiol-ene/yne Rea...mentioning

confidence: 99%

Recent Advances in Visible-Light Photoredox Catalysis for the Thiol-Ene/Yne Reactions

2022

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Visible-light photoredox catalysis has been established as a popular and powerful tool for organic transformations owing to its inherent characterization of environmental friendliness and sustainability in the past decades. The thiol-ene/yne reactions, the direct hydrothiolation of alkenes/alkynes with thiols, represents one of the most efficient and atom-economic approaches for the carbon-sulfur bonds construction. In traditional methodologies, harsh conditions such as stoichiometric reagents or a specialized UV photo-apparatus were necessary suffering from various disadvantages. In particular, visible-light photoredox catalysis has also been demonstrated to be a greener and milder protocol for the thiol-ene/yne reactions in recent years. Additionally, unprecedented advancements have been achieved in this area during the past decade. In this review, we will summarize the recent advances in visible-light photoredox catalyzed thiol-ene/yne reactions from 2015 to 2021. Synthetic strategies, substrate scope, and proposed reaction pathways are mainly discussed.

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“…The synthesis using economical, easily available visible-light sources have become vanguard in the synthetic chemistry as a prevailing approach for the activation of small molecules to furnish the desired products [64][65][66]. Burykina et al [67] synthesized different kinds of vinyl sulphides (35) in high yields with good selectivity using thiol-yne click reaction using visible light. The designed pathway is transition-metal-free and gave Markonvikov-type product through a radical photo-redox pathway (Figure 21 Method 1).…”

Section: Visible Light Assisted Click Chemistrymentioning

confidence: 99%

Role of Click Chemistry in Organic Synthesis

Sethiya¹,

Sahiba²,

Agarwal³

2021

Current Topics in Chirality - From Chemistry to Biology

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Click chemistry involves highly efficient organic reactions of two or more highly functionalized chemical entities under eco-benign conditions for the synthesis of different heterocycles. Several organic reactions such as nucleophilic ring-opening reactions, cyclo-additions, nucleophilic addition reactions, thiol-ene reactions, Diels Alder reactions, etc. are included in click reactions. These reactions have very important features i.e. high functional group tolerance, formation of a single product, high atom economy, high yielding, no need for column purification, etc. It also possesses several applications in drug discovery, supramolecular chemistry, material science, nanotechnology, etc. Being highly significant and valuable, we have elaborated on several aspects of click reactions in organic synthesis in this chapter. Recent advancements in the field of organic synthesis using click chemistry approach have been deliberated by citing last five years articles.

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Selectivity control in thiol–yne click reactions via visible light induced associative electron upconversion

Abstract: An associative electron upconversion is proposed as a key step determining the selectivity of the thiol-yne coupling. The developed synthetic approach provided an efficient tool to access a comprehensive range...

Cited by 61 publications

References 47 publications

ESI-MS Analysis of Thiol-yne Click Reaction in Petroleum Medium

ESI-MS Analysis of Thiol-yne Click Reaction in Petroleum Medium

Recent Advances in Visible-Light Photoredox Catalysis for the Thiol-Ene/Yne Reactions

Role of Click Chemistry in Organic Synthesis

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