scholarly journals Stereospecific Synthesis of Multi-Aryl Substituted Olefins and 1,3-Dienes via 1,4-Palladium Migration/Suzuki Coupling Sequence

2019 ◽  
Author(s):  
Meng-Yao Li ◽  
Pengbo Han ◽  
Tian-Jiao Hu ◽  
Qian Zhao ◽  
Dong Wei ◽  
...  
Keyword(s):  
Material Properties ◽  
Functional Group ◽  
Suzuki Coupling ◽  
Geometric Isomer ◽  
Vital Role ◽  
Stereospecific Synthesis ◽  
Efficient Synthesis ◽  
Stereochemical Control ◽  
Yield Values ◽  
Coupling Sequence

Multi-aryl substituted olefins and 1,3-dienes are important structural motifs in material molecules, and the stereochemistry of these structures exerts significant influence on the material properties. At present, the lack of effective methods to control the geometry of the double bonds has been a hurdle for the discovery of advanced material. We report herein the development of a 1,4-palladium migration/Suzuki coupling sequence for the efficient synthesis of these interesting molecules. A precise reactivity balance of the used organoboronates played a vital role in this process. The practicality of this method was demonstrated by the excellent capability and flexibility in stereochemical control, broad substrate scope, excellent functional group tolerance, as well as versatile conversion with obtained products and easy scalability. Furthermore, the power of this method is also highlighted by the aggregation-induced emission (AIE) feature studies of some obtained products, especially the easy accessibility of several geometric isomer pairs with a marked difference on photolumnescent quantum yield values.

scholarly journals Stereospecific Synthesis of Multi-Aryl Substituted Olefins and 1,3-Dienes via 1,4-Palladium Migration/Suzuki Coupling Sequence

2019 ◽  
Author(s):  
Meng-Yao Li ◽  
Pengbo Han ◽  
Tian-Jiao Hu ◽  
Qian Zhao ◽  
Dong Wei ◽  
...  
Keyword(s):  
Material Properties ◽  
Functional Group ◽  
Suzuki Coupling ◽  
Geometric Isomer ◽  
Vital Role ◽  
Stereospecific Synthesis ◽  
Efficient Synthesis ◽  
Stereochemical Control ◽  
Yield Values ◽  
Coupling Sequence

Multi-aryl substituted olefins and 1,3-dienes are important structural motifs in material molecules, and the stereochemistry of these structures exerts significant influence on the material properties. At present, the lack of effective methods to control the geometry of the double bonds has been a hurdle for the discovery of advanced material. We report herein the development of a 1,4-palladium migration/Suzuki coupling sequence for the efficient synthesis of these interesting molecules. A precise reactivity balance of the used organoboronates played a vital role in this process. The practicality of this method was demonstrated by the excellent capability and flexibility in stereochemical control, broad substrate scope, excellent functional group tolerance, as well as versatile conversion with obtained products and easy scalability. Furthermore, the power of this method is also highlighted by the aggregation-induced emission (AIE) feature studies of some obtained products, especially the easy accessibility of several geometric isomer pairs with a marked difference on photolumnescent quantum yield values.

An Efficient Synthesis of 2-Substituted Quinazolin-4(3H)-ones by Using Recyclable Wang Resin Supported Sulfonic Acid Catalyst

2020 ◽  
Vol 17 ◽  
Author(s):  
Kalyani K. ◽  
Srinivasa Reddy Kallam
Keyword(s):  
Sulfonic Acid ◽  
Functional Group ◽  
Acid Catalyst ◽  
Sulphonic Acid ◽  
Isatoic Anhydride ◽  
Efficient Synthesis ◽  
Wang Resin ◽  
Polymer Supported ◽  
High Yields

Abstract:: An efficient synthesis of 2-substituted Quinazolin-4(3H)-ones has been developed from isatoic anhydride with various amidoximes by using recyclable polymer supported sulphonic acid catalyst. Excellent functional group compatibil-ity and high yields are the important features of this protocol.

scholarly journals Effects of Molecular Weight of Functionalized Liquid Butadiene Rubber as a Processing Aid on the Properties of SSBR/Silica Compounds

Polymers ◽  
2021 ◽  
Vol 13 (6) ◽  
pp. 850
Author(s):  
Donghyuk Kim ◽  
Byungkyu Ahn ◽  
Kihyun Kim ◽  
JongYeop Lee ◽  
Il Jin Kim ◽  
...  
Keyword(s):  
Molecular Weight ◽  
Anionic Polymerization ◽  
High Performance ◽  
Crosslink Density ◽  
Functional Group ◽  
Vital Role ◽  
Butadiene Rubber ◽  
Molecular Weights ◽  
Mooney Viscosity ◽  
Silica Dispersion

Liquid butadiene rubber (LqBR) which used as a processing aid play a vital role in the manufacturing of high-performance tire tread compounds. However, the studies on the effect of molecular weight, microstructure, and functionalization of LqBR on the properties of compounds are still insufficient. In this study, non-functionalized and center-functionalized liquid butadiene rubbers (N-LqBR and C-LqBR modified with ethoxysilyl group, respectively) were synthesized with low vinyl content and different molecular weights using anionic polymerization. In addition, LqBR was added to the silica-filled SSBR compounds as an alternative to treated distillate aromatic extract (TDAE) oil, and the effect of molecular weight and functionalization on the properties of the silica-filled SSBR compound was examined. C-LqBR showed a low Payne effect and Mooney viscosity because of improved silica dispersion due to the ethoxysilyl functional group. Furthermore, C-LqBR showed an increased crosslink density, improved mechanical properties, and reduced organic matter extraction compared to the N-LqBR compound. LqBR reduced the glass transition temperature (Tg) of the compound significantly, thereby improving snow traction and abrasion resistance compared to TDAE oil. Furthermore, the energy loss characteristics revealed that the hysteresis loss attributable to the free chain ends of LqBR was dominant.

ChemInform Abstract: Efficient Synthesis of Racemic and Chiral Alkenyl Sulfoxides by Palladium-Catalyzed Suzuki Coupling.

ChemInform ◽  
2010 ◽  
Vol 41 (48) ◽  
pp. no-no
Author(s):  
Gisela Mancha ◽  
Ana B. Cuenca ◽  
Nuria Rodriguez ◽  
Mercedes Medio-Simon ◽  
Gregorio Asensio
Keyword(s):  
Suzuki Coupling ◽  
Efficient Synthesis ◽  
Palladium Catalyzed

Expedient iron-catalyzed stereospecific synthesis of triazines via cycloaddition of aziridines with diaziridines

2020 ◽  
Vol 56 (23) ◽  
pp. 3381-3384 ◽  
Author(s):  
Tanumay Sarkar ◽  
Kangkan Talukdar ◽  
Subhasish Roy ◽  
Tharmalingam Punniyamurthy
Keyword(s):  
Functional Group ◽  
Stereospecific Synthesis ◽  
Group Diversity

An iron(iii)-catalyzed [3+3]-annulation of bicyclic diaziridines and N-alkyl aziridines is developed for the synthesis of functionalized [1,2,4]-triazines. Ample substrate scope, functional group diversity, synthetic applications and enantiospecificity are the important practical features.

Synthesis of N-Propargyl Iminosugar Scaffolds for Compound Library Generation using Click Chemistry

2010 ◽  
Vol 63 (5) ◽  
pp. 821 ◽  
Author(s):  
Brendan L. Wilkinson ◽  
Laurent F. Bornaghi ◽  
Marie Lopez ◽  
Peter C. Healy ◽  
Sally-Ann Poulsen ◽  
...  
Keyword(s):  
Click Chemistry ◽  
Functional Group ◽  
Efficient Synthesis ◽  
Compound Library ◽  
Library Development

We have developed an efficient synthesis of N-propargyl iminosugars for use in diversity-oriented library development. Through a common, crystalline intermediate both piperidine and azepane scaffolds can be prepared with an alkyne functional group, allowing for further elaboration through reaction with azides.

An ortho-directed C–H borylation/Suzuki coupling sequence in the formation of biphenylbenzylic amines

2015 ◽  
Vol 2 (6) ◽  
pp. 661-664 ◽  
Author(s):  
Lillian V. A. Hale ◽  
David G. Emmerson ◽  
Emma F. Ling ◽  
Andrew J. Roering ◽  
Marissa A. Ringgold ◽  
...  
Keyword(s):  
Coupling Reaction ◽  
Suzuki Coupling ◽  
Purification Step ◽  
Benzylic Amines ◽  
Coupling Sequence

ortho-C–H borylation of benzylic amines has been used in conjunction with a Suzuki–Miyaura coupling reaction to access biphenylbenzylic amines in good yields and requiring a single purification step.

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