Chemical Communications, Journal Year: 2020, Volume and Issue: 56(50), P. 6850 - 6853
Published: Jan. 1, 2020
A simple nickel-catalyst for the chemo-selective alkylation of acetonitrile derivatives with primary alcohols is reported. This sustainable process resulted in up to 90% yield and generates water as by-product.
Language: Английский
Chemical Reviews, Journal Year: 2018, Volume and Issue: 119(4), P. 2524 - 2549
Published: Nov. 20, 2018
The conservation of our element resources is a fundamental challenge mankind. development alcohol refunctionalization reactions possible fossil carbon strategy since alcohols can be obtained from indigestible and abundantly available biomass. rare noble metals, frequently used in key technologies such as catalysis, might feasible by replacing them with highly abundant metals. alkylation amines related C–C coupling are early examples reactions. These follow mostly the borrowing hydrogen or autotransfer catalysis concept, many 3d-metal catalysts have been disclosed recent years. In this review, we summarize progress made developing Cu, Ni, Co, Fe, Mn for C–N bond formation using concept. We expect that findings field will inspire others to develop new efficient selective earth-abundant metal applications novel mediated
Language: Английский
Citations
753
ACS Central Science, Journal Year: 2021, Volume and Issue: 7(4), P. 570 - 585
Published: March 25, 2021
Borrowing hydrogen is a process that used to diversify the synthetic utility of commodity alcohols. A catalyst first oxidizes an alcohol by removing form reactive carbonyl compound. This intermediate can undergo diverse range subsequent transformations before returns "borrowed" liberate product and regenerate catalyst. In this way, alcohols may be as alkylating agents whereby sole byproduct one-pot reaction water. recent decades, significant advances have been made in area, demonstrating many effective methods access valuable products. outlook highlights diversity metal biocatalysts are available for approach, well various performed, focusing on selection most advances. By succinctly describing conveying versatility borrowing chemistry, we anticipate its uptake will increase across wider scientific audience, expanding opportunities further development.
Language: Английский
Citations
318
Chem, Journal Year: 2020, Volume and Issue: 7(5), P. 1180 - 1223
Published: Dec. 9, 2020
Language: Английский
Citations
217
Chemical Society Reviews, Journal Year: 2022, Volume and Issue: 51(11), P. 4386 - 4464
Published: Jan. 1, 2022
The emerging field of organometallic catalysis has shifted towards research on Earth-abundant transition metals due to their ready availability, economic advantage, and novel properties. In this case, manganese, the third most abundant transition-metal in Earth's crust, emerged as one leading competitors. Accordingly, a large number molecularly-defined Mn-complexes been synthesized employed for hydrogenation, dehydrogenation, hydroelementation reactions. regard, catalyst design is based three pillars, namely, metal-ligand bifunctionality, ligand hemilability, redox activity. Indeed, developed catalysts not only differ chelating atoms they possess but also working principles, thereby different turnover numbers product molecules. Hence, critical assessment molecularly defined manganese terms atoms, reaction conditions, mechanistic pathway, significant. Herein, we analyze complexes catalytic activity, versatility allow multiple transformations routes convert substrates target This article will be helpful get significant insight into design, aiding design.
Language: Английский
Citations
158
Chemical Reviews, Journal Year: 2024, Volume and Issue: 124(9), P. 6078 - 6144
Published: April 17, 2024
Alcohols are abundant and attractive feedstock molecules for organic synthesis. Many methods their functionalization require them to first be converted into a more activated derivative, while recent years have seen vast increase in the number of complexity-building transformations that directly harness unprotected alcohols. This Review discusses how transition metal catalysis can used toward this goal. These broadly classified three categories. Deoxygenative functionalizations, representing derivatization C–O bond, enable alcohol act as leaving group formation new C–C bonds. Etherifications, characterized by O–H represent classical reactivity has been modernized include mild reaction conditions, diverse partners, high selectivities. Lastly, chain reactions described, wherein acts mediator formal C–H alkyl backbone. Each these classes transformation will discussed context intermolecular arylation, alkylation, related reactions, illustrating alcohols harnessed
Language: Английский
Citations
35
Angewandte Chemie International Edition, Journal Year: 2018, Volume and Issue: 58(3), P. 775 - 779
Published: Nov. 20, 2018
Abstract A metal‐catalyzed methylation process has been developed. By employing an air‐ and moisture‐stable manganese catalyst together with isotopically labeled methanol, a series of D‐, CD 3 ‐, 13 C‐labeled products were obtained in good yields under mild reaction conditions water as the only byproduct.
Language: Английский
Citations
115
Organic Letters, Journal Year: 2019, Volume and Issue: 21(9), P. 3223 - 3227
Published: April 22, 2019
A sustainable synthesis of quinazoline and 2-aminoquinoline via acceptorless dehydrogenative annulation is presented. The reaction catalyzed by earth-abundant well-defined manganese complexes bearing NNS ligands. Furthermore, a one-pot synthetic strategy for the 2-alkylaminoquinolines through sequential N-alkylation has also been demonstrated.
Language: Английский
Citations
109
Organometallics, Journal Year: 2019, Volume and Issue: 38(8), P. 1815 - 1825
Published: April 12, 2019
The application of nontoxic, earth-abundant transition metals in place costly noble is a paramount goal catalysis and especially interesting if the air- moisture-stable ligand scaffold used. Herein, we report synthesis amines/imines directly from alcohol amines via hydrogen autotransfer or acceptorless dehydrogenation catalyzed by well-defined phosphine-free Mn complexes. Both imines can be obtained same set alcohols using catalyst, only tuning reaction conditions. amount nature base are found to highly important aspect for observed selectivity. primary secondary have been employed as substrates N-alkylation reaction. As highlight, showed chemoselective resveratrol derivatives. Furthermore, Mn-catalyzed dehydrogenative structurally 2,3-dihydro-1H-perimidines has also demonstrated. Density functional theory calculations were carried out model path calculate profile.
Language: Английский
Citations
91
Coordination Chemistry Reviews, Journal Year: 2020, Volume and Issue: 411, P. 213241 - 213241
Published: March 4, 2020
Language: Английский
Citations
82
The Journal of Organic Chemistry, Journal Year: 2019, Volume and Issue: 84(12), P. 7927 - 7935
Published: May 22, 2019
A general and chemoselective catalytic alkylation of nitriles using a homogeneous nonprecious manganese catalyst is presented. This reaction uses naturally abundant alcohols readily available as coupling partners. The tolerates wide range functional groups heterocyclic moieties, efficiently providing useful cyanoalkylated products with water the only side product. Importantly, methanol can be used C1 source C-methylation achieved. mechanistic investigations support multiple role metal-ligand catalyst, dehydrogenative activation alcohol, α-C-H nitrile, hydrogenation in-situ-formed unsaturated intermediate.
Language: Английский
Citations
81