4437-80-3Relevant articles and documents
Gold(I)-catalyzed formation of 4-alkylidene-1,3-dioxolan-2-ones from propargylic tert-butyl carbonates
Buzas, Andrea,Gagosz, Fabien
, p. 515 - 518 (2006)
A study concerning the gold(I)-catalyzed rearrangement of propargylic tert-butyl carbonates into 4-alkylidene-1,3-dioxolan-2-ones is described. The mild reaction conditions employed allow the efficient synthesis of a variety of cyclic carbonates that would be less conveniently obtained using reported methods. Variability in the structure of the final product has been observed and is significantly dependent on the nature of the substituent attached to the alkyne moiety.
Nickel-Catalyzed CO2Rearrangement of Enol Metal Carbonates for the Efficient Synthesis of β-Ketocarboxylic Acids
Ninokata, Ryo,Yamahira, Tatsuya,Onodera, Gen,Kimura, Masanari
, p. 208 - 211 (2017)
4-Methylene-1,3-dioxolan-2-ones underwent oxidative addition of a Ni0catalyst in the presence of Me2Al(OMe), followed by a coupling reaction with alkynes, to form δ,?-unsaturated β-ketocarboxylic acids with high regio- and stereoselectivity. The reaction proceeds by [1,3] rearrangement of an enol metal carbonate intermediate and the formal reinsertion of CO2.
Ag Nanoparticles Supported on a Resorcinol-Phenylenediamine-Based Covalent Organic Framework for Chemical Fixation of CO2
Chakraborty, Debanjan,Shekhar, Pragalbh,Singh, Himan Dev,Kushwaha, Rinku,Vinod,Vaidhyanathan, Ramanathan
, p. 4767 - 4773 (2019)
Covalent organic frameworks are a new class of crystalline organic polymers possessing a high surface area and ordered pores. Judicious selection of building blocks leads to strategic heteroatom inclusion into the COF structure. Owing to their high surface area, exceptional stability and molecular tunability, COFs are adopted for various potential applications. The heteroatoms lining in the pores of COF favor synergistic host–guest interaction to enhance a targeted property. In this report, we have synthesized a resorcinol-phenylenediamine-based COF which selectively adsorbs CO2 into its micropores (12 ?). The heat of adsorption value (32 kJ mol?1) obtained from the virial model at zero-loading of CO2 indicates its favorable interaction with the framework. Furthermore, we have anchored small-sized Ag nanoparticles (≈4–5 nm) on the COF and used the composite for chemical fixation of CO2 to alkylidene cyclic carbonates by reacting with propargyl alcohols under ambient conditions. Ag@COF catalyzes the reaction selectively with an excellent yield of 90 %. Recyclability of the catalyst has been demonstrated up to five consecutive cycles. The post-catalysis characterizations reveal the integrity of the catalyst even after five reaction cycles. This study emphasizes the ability of COF for simultaneous adsorption and chemical fixation of CO2 into corresponding cyclic carbonates.
Room-Temperature Synthesis of a Hollow Microporous Organic Polymer Bearing Activated Alkyne IR Probes for Nonradical Thiol-yne Click-Based Post-Functionalization
Park, Jong In,Jang, June Young,Ko, Yoon-Joo,Lee, Sang Moon,Kim, Hae Jin,Jang, Hye-Young,Ko, Kyoung Chul,Son, Seung Uk
, p. 1398 - 1402 (2021)
This work shows that hollow microporous organic polymer (H-MOP-A) with activated internal alkynes as IR probes can be prepared by template synthesis based on acyl Sonogashira-Hagihara coupling at room temperature. The H-MOP-A is a versatile platform in the main chain PSM based on nonradical thiol-yne click reaction. Moreover, an IR peak of internal alkynes in the H-MOP-A is very intense and could be utilized in the monitoring of thiol-yne click-based main chain PSM. The functionalized H-MOP-A with carboxylic acids (H-MOP-CA) showed efficient adsorption toward Ag+ ions. The resultant H-MOP-CA-Ag showed excellent performance in the CO2 fixation to α-alkylidene cyclic compounds.
PHOSPHINE CATALYSED SYNTHESIS OF UNSATURATED CYCLIC CARBONATES FROM CARBON DIOXIDE AND PROPARGYLIC ALCOHOLS
Furnier, Jean,Bruneau, Christian,Dixneuf, Pierre H.
, p. 3981 - 3982 (1989)
A new route to α-methylene cyclic carbonates is reported, by direct reaction of carbon dioxide with α-ethynyl alcohols in the presence of a catalytic amount of a phosphine.
Copper-catalysed synthesis of α-alkylidene cyclic carbonates from propargylic alcohols and CO2
Cervantes-Reyes, Alejandro,Farshadfar, Kaveh,Rudolph, Matthias,Rominger, Frank,Schaub, Thomas,Ariafard, Alireza,Hashmi
supporting information, p. 889 - 897 (2021/02/09)
We report a N-heterocyclic carbene copper(i) complex-catalysed formal cycloaddition between readily available propargylic alcohols and carbon dioxide at room temperature. By using the combination of a sterically demandingBPDPrCuCl complex (BPDPr = 1,3-bis(2,6-diisopropylphenyl)-1,3-diazonine-2-ylidene) and CsF, as catalytic system, primary propargylic alcohols are efficiently converted to the corresponding α-alkylidene cyclic carbonates. Gram scale (up to 89% yield) and reusability experiments (74% global yield, turnover number value = 103) showcase the robustness of the catalytic system. This practically simple protocol also tolerates secondary and tertiary propargylic alcohols under CO2at atmospheric pressure, enabling the direct synthesis of substituted and unsubstituted α-alkylidene cyclic carbonates at room temperature.
Synthesis of α-alkylidene cyclic carbonatesviaCO2fixation under ambient conditions promoted by an easily available silver carbamate
Bresciani, Giulio,Bortoluzzi, Marco,Ghelarducci, Claudia,Marchetti, Fabio,Pampaloni, Guido
, p. 4340 - 4346 (2021/03/15)
The simple and cost-effective compound [Ag(O2CNEt2)], in combination with PPh3, works as an effective catalytic precursor in the carboxylation of propargyl alcohols at ambient temperature and atmospheric CO2pressure, and in most cases under solventless conditions. The silver carbamate revealed a better performance than commercial silver oxide, Ag2O, and allowed to obtain a series of α-alkylidene cyclic carbonates in high yields.
