Stereoselective Synthesis of (E)- and (Z)-Triethoxy(vinyl-d2)silanes by Hydrosilylation of Acetylene-d2

Gordillo, Álvaro; Forigua, Johan; López-Mardomingo, Carmen; Jesús, Ernesto de

doi:10.1021/om101127t

Cited by 16 publications

(4 citation statements)

References 29 publications

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“…The products were characterized by 1 H NMR, 13 C NMR, and GC–MS. All the spectroscopic data were in agreement with those previously reported for the following compounds: ( E )-1,1'-(ethene-1,2-diylbis(4,1-phenylene))diethanone ( 17 ) [ 68 ] and ( E )-1,2-bis(3,5-dimethoxyphenyl)ethane ( 18 ) [ 69 ].…”

Section: Methodssupporting

confidence: 89%

An effective Pd nanocatalyst in aqueous media: stilbene synthesis by Mizoroki–Heck coupling reaction under microwave irradiation

García

Uberman

Martín

2017

Beilstein J. Org. Chem.

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Aqueous Mizoroki–Heck coupling reactions under microwave irradiation (MW) were carried out with a colloidal Pd nanocatalyst stabilized with poly(N-vinylpyrrolidone) (PVP). Many stilbenes and novel heterostilbenes were achieved in good to excellent yields starting from aryl bromides and different olefins. The reaction was carried out in a short reaction time and with low catalyst loading, leading to high turnover frequency (TOFs of the order of 100 h−1). The advantages like operational simplicity, high robustness, efficiency and turnover frequency, the utilization of aqueous media and simple product work-up make this protocol a great option for stilbene syntheses by Mizoroki–Heck reaction.

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Section: Methodssupporting

confidence: 89%

An effective Pd nanocatalyst in aqueous media: stilbene synthesis by Mizoroki–Heck coupling reaction under microwave irradiation

García

Uberman

Martín

2017

Beilstein J. Org. Chem.

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“…The addition of alkoxysilanes to the C=C bonds is a fundamental transformation in the production of a wide range of SCAs with short alkyl spacers between the alkoxysilyl group and the reactive organic function. Within hydrosilylation reactions, various propylalkoxysilanes with a different group at 3 position, including halogen, [4] amines, [5] epoxides, [6] or vinyl [7] groups, were synthesized. On the other hand, coupling agents with sulfur, i. e., 3‐mercaptopropyl‐triethoxysilane and its S ‐octanoyl analog (commercially known as NXT®), whose synthesis by hydrosilylation is difficult due to the commonly observed poisoning of the catalyst, are prepared using substitution reactions of 3‐chloropropyltriethoxysilane with sodium sulfide [8] or sodium octanoylsulfanide, [9] respectively.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Bio‐Based Silane Coupling Agents by the Modification of Eugenol

et al. 2021

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A simple method for the synthesis of new bio-based silane coupling agents (SCAs) with a terpene aromatic core by the functionalization of cheap, natural eugenol and its sulfur derivatives using the hydrosilylation of the C=C bonds with HSi(OEt) 3 , followed by nucleophilic substitution reactions of OH/SH groups is presented. The obtained alkoxysilanes possess different polymerreactive functionalities (alkenyl, epoxide, thiirane, thiocarbamoyl, thioester, thioether moieties). This new group of biogenic SCAs was fully characterized using 1 H, 13 C, 29 Si NMR, FT-IR, GC-MS, and HRMS or elemental analysis. Examples of their application as additives to tire rubbers and their influence on several factors are also discussed.

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“…Compared to the literature, one can easily highlight the advantages of atom-economic D-labeling through the use of C 2 D 2 . Alternative synthetic approaches to incorporate deuterium labels are based on base- or metal-catalyzed exchange reactions [ 81 , 82 , 83 , 84 , 85 , 86 ], D 2 -gas use [ 87 ], or previously labeled compounds [ 88 , 89 , 90 ]. Exchange reactions consume a significant amount of deuterated starting substrate when the desired product is mixed with a many-fold excess of a deuterated source several times [ 91 , 92 ].…”

Section: Resultsmentioning

confidence: 99%

3D Printing to Increase the Flexibility of the Chemical Synthesis of Biologically Active Molecules: Design of On-Demand Gas Generation Reactors

Erokhin

Gordeev

Samoylenko

et al. 2021

IJMS

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The development of new drugs is accelerated by rapid access to functionalized and D-labeled molecules with improved activity and pharmacokinetic profiles. Diverse synthetic procedures often involve the usage of gaseous reagents, which can be a difficult task due to the requirement of a dedicated laboratory setup. Here, we developed a special reactor for the on-demand production of gases actively utilized in organic synthesis (C2H2, H2, C2D2, D2, and CO2) that completely eliminates the need for high-pressure equipment and allows for integrating gas generation into advanced laboratory practice. The reactor was developed by computer-aided design and manufactured using a conventional 3D printer with polypropylene and nylon filled with carbon fibers as materials. The implementation of the reactor was demonstrated in representative reactions with acetylene, such as atom-economic nucleophilic addition (conversions of 19–99%) and nickel-catalyzed S-functionalization (yields 74–99%). One of the most important advantages of the reactor is the ability to generate deuterated acetylene (C2D2) and deuterium gas (D2), which was used for highly significant, atom-economic and cost-efficient deuterium labeling of S,O-vinyl derivatives (yield 68–94%). Successful examples of their use in organic synthesis are provided to synthesize building blocks of heteroatom-functionalized and D-labeled biologically active organic molecules.

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Stereoselective Synthesis of (E)- and (Z)-Triethoxy(vinyl-d₂)silanes by Hydrosilylation of Acetylene-d₂

Cited by 16 publications

References 29 publications

An effective Pd nanocatalyst in aqueous media: stilbene synthesis by Mizoroki–Heck coupling reaction under microwave irradiation

An effective Pd nanocatalyst in aqueous media: stilbene synthesis by Mizoroki–Heck coupling reaction under microwave irradiation

Synthesis of Bio‐Based Silane Coupling Agents by the Modification of Eugenol

3D Printing to Increase the Flexibility of the Chemical Synthesis of Biologically Active Molecules: Design of On-Demand Gas Generation Reactors

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