Renewable Linear Alpha-Olefins by Base-Catalyzed Dehydration of Biologically-Derived Fatty Alcohols

2021 ◽  
Author(s):  
Daniel James McClelland ◽  
Bo-Xun Wang ◽  
William Cordell ◽  
Yoel Cortes-Pena ◽  
Elise Gilcher ◽  
...  

Base catalysts were studied for the dehydration of fatty alcohols to linear alpha olefins (LAOs). For the dehydration of 1-octanol to 1-octene, 15%Cs/SiO2 catalyst was 56% selective at 10% conversion....

1998 ◽  
Vol 39 (10) ◽  
pp. 1907-1917 ◽  
Author(s):  
Edna S. Kaneshiro ◽  
Zengkui Guo ◽  
Donggeun Sul ◽  
Kathryn A. Kallam ◽  
Koka Jayasimhulu ◽  
...  

2021 ◽  
Vol 6 (9) ◽  
pp. 2335-2342
Author(s):  
Sirigireddy Sudharsan Reddy ◽  
Anuraj Varyambath ◽  
Reddi Mohan Naidu Kalla ◽  
Wenliang Song ◽  
Il Kim
Keyword(s):  

2021 ◽  
Vol 12 (1) ◽  
Author(s):  
Peng-Ying Jiang ◽  
Kai-Fang Fan ◽  
Shaoyu Li ◽  
Shao-Hua Xiang ◽  
Bin Tan

AbstractAs an important platform molecule, atropisomeric QUINOL plays a crucial role in the development of chiral ligands and catalysts in asymmetric catalysis. However, efficient approaches towards QUINOL remain scarce, and the resulting high production costs greatly impede the related academic research as well as downstream industrial applications. Here we report a direct oxidative cross-coupling reaction between isoquinolines and 2-naphthols, providing a straightforward and scalable route to acquire the privileged QUINOL scaffolds in a metal-free manner. Moreover, a NHC-catalyzed kinetic resolution of QUINOL N-oxides with high selectivity factor is established to access two types of promising axially chiral Lewis base catalysts in optically pure forms. The utility of this methodology is further illustrated by facile transformations of the products into QUINAP, an iconic ligand in asymmetric catalysis.


Molecules ◽  
2021 ◽  
Vol 26 (4) ◽  
pp. 1159
Author(s):  
Eskedar Tessema ◽  
Vijayanath Elakkat ◽  
Chiao-Fan Chiu ◽  
Jing-Hung Zheng ◽  
Ka Long Chan ◽  
...  

Phospha-Michael addition, which is the addition reaction of a phosphorus-based nucleophile to an acceptor-substituted unsaturated bond, certainly represents one of the most versatile and powerful tools for the formation of P-C bonds, since many different electrophiles and P nucleophiles can be combined with each other. This offers the possibility to access many diversely functionalized products. In this work, two kinds of basic pyridine-based organo-catalysts were used to efficiently catalyze phospha-Michael addition reactions, the 4-N,N-dimethylaminopyridinium saccharinate (DMAP·Hsac) salt and a fluorous long-chained pyridine (4-Rf-CH2OCH2-py, where Rf = C11F23). These catalysts have been synthesized and characterized by Lu’s group. The phospha-Michael addition of diisopropyl, dimethyl or triethyl phosphites to α, β-unsaturated malonates in the presence of those catalysts showed very good reactivity with high yield at 80–100 °C in 1–4.5 h with high catalytic recovery and reusability. With regard to significant catalytic recovery, sometimes more than eight cycles were observed for DMAP·Hsac adduct by using non-polar solvents (e.g., ether) to precipitate out the catalyst. In the case of the fluorous long-chained pyridine, the thermomorphic method was used to efficiently recover the catalyst for eight cycles in all the reactions. Thus, the easy separation of the catalysts from the products revealed the outstanding efficacy of our systems. To our knowledge, these are good examples of the application of recoverable organo-catalysts to the DMAP·Hsac adduct by using non-polar solvent and a fluorous long-chained pyridine under the thermomorphic mode in phospha-Michael addition reactions.


2021 ◽  
Author(s):  
Jin Hee Lee ◽  
Hack-Keun Lee ◽  
Kwangsoo Kim ◽  
Geunbae Rhim ◽  
Min Hye Youn ◽  
...  

C5−C13 linear alpha() olefins (LAOs) are high-value-added chemicals acknowledged by industry. However, using catalysts to elevate the activity and selectivity of LAOs remains a major challenge for Fischer–Tropsch synthesis (FTS)....


Synlett ◽  
2021 ◽  
Author(s):  
Andrei V. Malkov ◽  
Aleksandr E. Rubtsov

AbstractAsymmetric crotylation has firmly earned a place among the set of valuable synthetic tools for stereoselective construction of carbon skeletons. For a long time the field was heavily dominated by reagents bearing stoichiometric chiral auxiliaries, but now catalytic methods are gradually taking center stage, and the area continues to develop rapidly. This account focuses primarily on preformed organometallic reagents based on silicon and, to some extent, boron. It narrates our endeavors to design new and efficient chiral Lewis base catalysts for the asymmetric addition of crotyl(trichloro)silanes to aldehydes. It also covers the development of a novel protocol for kinetic resolution of racemic secondary allylboronates to give enantio- and diastereomerically enriched linear homoallylic alcohols. As a separate topic, cross-crotylation of aldehydes by using enantiopure branched homoallylic alcohols as a source of crotyl groups is discussed. Finally, the synthetic credentials of the developed methodology are illustrated by total syntheses of marine natural products, in which crotylation plays a key role in setting up stereogenic centers.1 Introduction2 Pyridine N-Oxides as Lewis Base Catalysts3 Bipyridine N,N′-Dioxides as Lewis Base Catalysts4 Chiral Allylating Reagents5 Synthetic Applications6 Concluding Remarks


2021 ◽  
pp. 125054
Author(s):  
Mani Jayakumar ◽  
Natchimuthu Karmegam ◽  
Marttin Paulraj Gundupalli ◽  
Kaleab Bizuneh Gebeyehu ◽  
Belete Tessema Asfaw ◽  
...  

2021 ◽  
Vol 332 ◽  
pp. 115881
Author(s):  
Loukia Maritsa ◽  
Sonia Martel ◽  
Rocio Barros ◽  
Alfredo Bol ◽  
Santiago Aparicio

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