Mild deuteration method of terminal alkynes in heavy water using reusable basic resin

Yamada, Tsuyoshi; Park, Kwihwan; Monguchi, Yasunari; Sawama, Yoshinari; Sajiki, Hironao

doi:10.1039/c5ra18921g

Cited by 19 publications

(10 citation statements)

References 27 publications

(6 reference statements)

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“…Yamada et al [37] developed a mild and efficient approach for the deuteration of terminal alkynes through the use of heterogeneous basic polystyrene resin (WA30) under mild conditions in the presence of D 2 O. Based on their findings, a wide range of functionalities such as nitro, propargyl ester, sulfide, benzyl ether, and others were very well-tolerated under such conditions.…”

Section: Solvent and Metal-free Recyclable Catalystsmentioning

confidence: 99%

Recyclable Catalysts for Alkyne Functionalization

2021

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In this review, we present an assessment of recent advances in alkyne functionalization reactions, classified according to different classes of recyclable catalysts. In this work, we have incorporated and reviewed the activity and selectivity of recyclable catalytic systems such as polysiloxane-encapsulated novel metal nanoparticle-based catalysts, silica–copper-supported nanocatalysts, graphitic carbon-supported nanocatalysts, metal organic framework (MOF) catalysts, porous organic framework (POP) catalysts, bio-material-supported catalysts, and metal/solvent free recyclable catalysts. In addition, several alkyne functionalization reactions have been elucidated to demonstrate the success and efficiency of recyclable catalysts. In addition, this review also provides the fundamental knowledge required for utilization of green catalysts, which can combine the advantageous features of both homogeneous (catalyst modulation) and heterogeneous (catalyst recycling) catalysis.

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Section: Solvent and Metal-free Recyclable Catalystsmentioning

confidence: 99%

Recyclable Catalysts for Alkyne Functionalization

2021

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“…To gain some insight into the proposed mechanism, isotopic labeling studies were performed. The terminal position of the alkyne was deuterated selectively using an amine appended resin (WA50) in accordance with the literature . Tracking the reaction progress using both 1 H and 2 H NMR spectroscopy whilst comparing the in situ data of the protic versus deuterated compounds shed light on the fate of the terminal alkynyl hydrogen atom and hence the reaction mechanism (see below, Scheme ).…”

Section: Methodsmentioning

confidence: 99%

“…The terminal position of the alkyne was deuterated selectively using an amine appended resin (WA50) in accordance with the literature. [17] Tracking the reactionp rogress using both 1 Ha nd 2 HNMR spectroscopy whilst comparing the in situ data of the protic versus deuterated compounds shed light on the fate of the terminal alkynyl hydrogen atom and hence the reactionm echanism (see below,S cheme4). A 1 Hr esonancea td = 6.6 ppm is observed in 3a for the proton on the carbon adjacent to boron, whichi s evidently absent in 3a D (Figure 2).…”

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confidence: 99%

Divergent Elementoboration: 1,3‐Haloboration versus 1,1‐Carboboration of Propargyl Esters

Wilkins

Soltani

Lawson

et al. 2018

Chemistry A European J

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This work showcases the 1,3‐haloboration reaction of alkynes in which boron and chlorine add to propargyl systems in a proposed sequential oxazoliumborate formation with subsequent ring‐opening and chloride migration. In addition, the functionalization of these propargyl esters with dimethyl groups in the propargylic position leads to stark differences in reactivity whereby a formal 1,1‐carboboration prevails to give the 2,2‐dichloro‐3,4‐dihydrodioxaborinine products as an intramolecular chelate. Density functional theory calculations are used to rationalize the distinct carboboration and haloboration pathways. Significantly, this method represents a metal‐free route to highly functionalized compounds in a single step to give structurally complex products.

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“…[74] be removed easily by filtration and repeatedly reused. [80] Erdogan et al [81] adopted a bifunctional alkene-zipper catalyst for the synthesis of deuterium-labeled alkenes. With acetone/ D 2 O as a cosolvent, high steric selectivity of (E)-alkenes was achieved.…”

Section: Aliphatic Hydrocarbonsmentioning

confidence: 99%

“…HÀ D exchange of terminal alkynes. [80] Figure 11. Catalytic performance for H À D exchange of anilines.…”

Section: Alcoholsmentioning

confidence: 99%

Recent Advances in the Synthesis of Deuterium‐Labeled Compounds

2021

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Deuterium‐labeled compounds are of importance in chemical, environmental, and biological fields. Preparation methods for deuterium‐labeled compounds have been studied extensively in response to increasing demand for these chemicals. In this review, we summarize recent advances in synthetic methods and present a comprehensive overview of diverse routes, including conventional deuteration and hydrogen‐deuterium exchange. Deuteration by the classical process, which starts from appropriate available labeled precursors, is introduced for different reaction types. Key features of hydrogen‐deuterium exchange are elaborated in detail from the perspective of the catalyst and the chemical structure of the substrate. Regioselective deuteration at the target position is discussed because of the role of stereospecific deuterium labeling in medicine. Finally, challenges and future prospects of these processes are discussed to provide a general guideline for the synthesis of deuterium‐labeled compounds.

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Mild deuteration method of terminal alkynes in heavy water using reusable basic resin

Abstract: The mild and efficient deuteration method of terminal alkynes using a reusable anion exchange resin in D2O has been developed.

Cited by 19 publications

References 27 publications

Recyclable Catalysts for Alkyne Functionalization

Recyclable Catalysts for Alkyne Functionalization

Divergent Elementoboration: 1,3‐Haloboration versus 1,1‐Carboboration of Propargyl Esters

Recent Advances in the Synthesis of Deuterium‐Labeled Compounds

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