Organocatalysis and Transition-Metal Catalysis: Key Trends in Synthetic Chemistry and Challenges

Topic Information

Dear Colleagues,

Organocatalysis and transition metal catalysis play a fundamental role in current organic synthesis, for the production of high-value-added molecules starting from simple and readily available building blocks under greener and more sustainable conditions. The importance of this topic is clearly demonstrated by the Nobel prize awarded in 2021 to Benjamin List and David MacMillan “for the development of asymmetric organocatalysis” and in 2010 to Richard F. Heck, Ei-ichi Negishi, and Akira Suzuki “for palladium-catalyzed cross couplings in organic synthesis”. In fact, organocatalysis and transition metal catalysis are powerful synthetic methodologies which allow the preparation of complex, multifunctionalized molecules in one step via the assembly of simple building blocks through an ordered sequence of mechanistic steps promoted by either an organic species or a metal center. Although enormous progress has been made in this field in recent decades, this kind of chemistry is bound to become even more important in the future of organic synthesis, owing to the more stringent requirements for the development of highly step- and atom economic sustainable processes, and will continue to attract the interest of chemists around the world, both in academia and industry.

Prof. Dr. Bartolo Gabriele
Prof. Dr. Raffaella Mancuso
Prof. Dr. Zhengguo Cai
Topic Editors

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Participating Journals

Journal Name	Impact Factor	CiteScore	Launched Year	First Decision (median)	APC
Catalysts catalysts	4.0	7.6	2011	13.9 Days	CHF 2200
Chemistry chemistry	2.4	3.9	2019	17.2 Days	CHF 1800
Molbank molbank	0.4	0.9	1997	13.5 Days	CHF 500
Molecules molecules	4.6	8.6	1996	15.1 Days	CHF 2700

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Published Papers (7 papers)

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Supplementary File 2 (MOL, 2 KiB)
Supplementary File 3 (INCHI, 823 B)
Supplementary File 4 (MOL, 2 KiB)

5 pages, 544 KiB  

Open AccessShort Note

1-{(1S,2S,4R)-7,7-Dimethyl-1-[(pyrrolidin-1-yl)methyl]bicyclo [2.2.1]heptan-2-yl}-1H-benzo[d]imidazole

by Luka Ciber, Franc Požgan, Jurij Svete, Bogdan Štefane and Uroš Grošelj

Molbank 2023, 2023(1), M1538; https://doi.org/10.3390/M1538 - 6 Jan 2023

Cited by 1 | Viewed by 2777

Abstract

A three-step synthesis of 1-{(1S,2S,4R)-7,7-dimethyl-1-[(pyrrolidin-1-yl)methyl]bicyclo[2.2.1]heptan-2-yl}-1H-benzo[d]imidazole, prepared from camphor derived diamine, is disclosed. The absolute configuration at the chiral center bearing benzo[d]imidazole moiety was confirmed by NOESY. The structure of a newly [...] Read more.

A three-step synthesis of 1-{(1S,2S,4R)-7,7-dimethyl-1-[(pyrrolidin-1-yl)methyl]bicyclo[2.2.1]heptan-2-yl}-1H-benzo[d]imidazole, prepared from camphor derived diamine, is disclosed. The absolute configuration at the chiral center bearing benzo[d]imidazole moiety was confirmed by NOESY. The structure of a newly synthesized compound was confirmed by ¹H- and ¹³C-NMR, 2D NMR, IR spectroscopy, and high resolution mass-spectrometry. Full article

(This article belongs to the Topic Organocatalysis and Transition-Metal Catalysis: Key Trends in Synthetic Chemistry and Challenges)

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Supplementary File 1 (ZIP, 1295 KiB)

18 pages, 1389 KiB  

Open AccessArticle

Squaramide-Catalyzed Asymmetric Mannich Reaction between 1,3-Dicarbonyl Compounds and Pyrazolinone Ketimines: A Pathway to Enantioenriched 4-Pyrazolyl- and 4-Isoxazolyl-4-aminopyrazolone Derivatives

by Marta Gil-Ordóñez, Camille Aubry, Cristopher Niño, Alicia Maestro and José M. Andrés

Molecules 2022, 27(20), 6983; https://doi.org/10.3390/molecules27206983 - 17 Oct 2022

Cited by 4 | Viewed by 2900

Abstract

A series of N-Boc ketimines derived from pyrazolin-5-ones have been used as electrophiles in enantioselective Mannich reactions with different 1,3-dicarbonyl compounds. This method provides a direct pathway to access the 4-amino-5-pyrazolone derivatives bearing a quaternary substituted stereocenter and containing two privileged structure motifs, [...] Read more.

A series of N-Boc ketimines derived from pyrazolin-5-ones have been used as electrophiles in enantioselective Mannich reactions with different 1,3-dicarbonyl compounds. This method provides a direct pathway to access the 4-amino-5-pyrazolone derivatives bearing a quaternary substituted stereocenter and containing two privileged structure motifs, the β-diketone and pyrazolinone substructures. The adducts were obtained in excellent yields (up to 90%) and enantioselectivities (up to 94:6 er) by employing a very low loading of 2 mol% of a quinine-derived bifunctional squaramide as an organocatalyst for a wide range of substrates. In addition, the utility of the obtained products was demonstrated through one step transformations to enantioenriched diheterocyclic systems (4-pyrazolyl-pyrazolone and 4-isoxazolyl-pyrazolone), potentially promising candidates for drug discovery. Full article

(This article belongs to the Topic Organocatalysis and Transition-Metal Catalysis: Key Trends in Synthetic Chemistry and Challenges)

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Supplementary material:
Supplementary File 1 (PDF, 277 KiB)
Supplementary File 2 (MOL, 9 KiB)
Supplementary File 3 (INCHI, 6 KiB)
Supplementary File 4 (MOL, 10 KiB)
Supplementary File 5 (CIF, 348 KiB)
Supplementary File 6 (ZIP, 166 KiB)

8 pages, 2921 KiB  

Open AccessCommunication

Synthesis, Characterization, and Structure of Mixed-Ligand Cobalt (II) Complex with N, O Donor Sites

by Debdas Mandal, Anwesha Haldar, Priyanka Chakraborty and Rakesh Ganguly

Molbank 2022, 2022(3), M1447; https://doi.org/10.3390/M1447 - 16 Sep 2022

Cited by 2 | Viewed by 2196

Abstract

A mononuclear octahedral mixed-ligand cobalt (II) complex [Co(H₂L)(PhCOO)₂] (1) has been prepared by using H₂L (N,N′-dimethyl-N,N′-bi(2-hydroxy-3,5-di methyl benzyl)-ethylenediamine) as a facially coordinating tetradentate ligand with a N [...] Read more.

A mononuclear octahedral mixed-ligand cobalt (II) complex [Co(H₂L)(PhCOO)₂] (1) has been prepared by using H₂L (N,N′-dimethyl-N,N′-bi(2-hydroxy-3,5-di methyl benzyl)-ethylenediamine) as a facially coordinating tetradentate ligand with a N₂O₂ donor center along with sodium benzoate as an ancillary ligand. Complex 1 has been characterized by a single-crystal X-ray diffraction study, as well as by other spectroscopic tools. The complex crystallizes in the monoclinic space group C₂ with a = 31.73(3) Å, b = 7.868(3) Å, c = 19.131(15) Å, and β = 125.25(3)°. The single-crystal X-ray diffraction study shows that in the mononuclear cobalt (II) complex [Co(H₂L)(PhCOO)₂] (1), the metal center adopts an octahedral environment. Full article

(This article belongs to the Topic Organocatalysis and Transition-Metal Catalysis: Key Trends in Synthetic Chemistry and Challenges)

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Supplementary File 1 (ZIP, 964 KiB)

11 pages, 1872 KiB  

Open AccessArticle

Photocatalytic Isomerization of (E)-Anethole to (Z)-Anethole

by Marvin Korff, Tiffany O. Paulisch, Frank Glorius, Nikos L. Doltsinis and Bernhard Wünsch

Molecules 2022, 27(16), 5342; https://doi.org/10.3390/molecules27165342 - 22 Aug 2022

Cited by 8 | Viewed by 3439

Abstract

Natural product (E)-anethole was isomerized to (Z)-anethole in a photocatalytic reaction. For this purpose, a self-designed cheap photoreactor was constructed. Among 11 photosensitizers (organo and metal complex compounds), Ir(p-tBu-ppy)₃ led to the highest conversion. Triplet energies [...] Read more.

Natural product (E)-anethole was isomerized to (Z)-anethole in a photocatalytic reaction. For this purpose, a self-designed cheap photoreactor was constructed. Among 11 photosensitizers (organo and metal complex compounds), Ir(p-tBu-ppy)₃ led to the highest conversion. Triplet energies of (E)- and (Z)-anethole were predicted theoretically by DFT calculations to support the selection of appropriate photosensitizers. A catalyst loading of 0.1 mol% gave up to 90% conversion in gram scale. Further additives were not required and mild irradiation with light of 400 nm overnight was sufficient. As a proof of concept, (E)- and (Z)-anethole were dihydroxylated diastereoselectively to obtain diastereomerically pure like- and unlike-configured diols, respectively. Full article

(This article belongs to the Topic Organocatalysis and Transition-Metal Catalysis: Key Trends in Synthetic Chemistry and Challenges)

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Supplementary material:
Supplementary File 1 (PDF, 562 KiB)
Supplementary File 2 (MOL, 2 KiB)
Supplementary File 3 (INCHI, 991 B)
Supplementary File 4 (MOL, 2 KiB)

9 pages, 2028 KiB  

Open AccessShort Note

Chlorido-(η⁶-p-cymene)-(bis(pyrazol-1-yl)methane-κ²N,N′)Osmium(II) Tetrafluoroborate, C₁₇H₂₂BClF₄N₄Os

by Allen Mambanda, Amos K. Kanyora, Peter Ongoma, Joel Gichumbi and Reinner O. Omondi

Molbank 2022, 2022(3), M1429; https://doi.org/10.3390/M1429 - 18 Aug 2022

Viewed by 2036

Abstract

The powder of the arene osmium(II) complex, [Os(II)(dpzm)(η⁶-p-cym)Cl]BF₄ (dpzm = di(1H-pyrazol-1-yl)methane; η⁶-p-cym = para-cymene), with a formula of C₁₇H₂₂BClF₄N₄Os (referred to herein [...] Read more.

The powder of the arene osmium(II) complex, [Os(II)(dpzm)(η⁶-p-cym)Cl]BF₄ (dpzm = di(1H-pyrazol-1-yl)methane; η⁶-p-cym = para-cymene), with a formula of C₁₇H₂₂BClF₄N₄Os (referred to herein as 1) was isolated from the reaction of [(η⁶-p-cym)Os(μ-Cl)(Cl)]₂ with dpzm dissolved in acetonitrile and under a flow of nitrogen gas. It was characterized by spectroscopic techniques (viz., FTIR, ¹H NMR, UV-Visible absorption). Yellow crystal blocks of 1 were grown by the slow evaporation from the methanolic solution of its powder. The single-crystal X-ray structure of 1 was solved by diffraction analysis on a Bruker APEX Duo CCD area detector diffractometer using the Cu(K_α), λ = 1.54178 Å as the radiation source, and 1 crystallizes in the monoclinic crystal system and the C2/c (no. 15) space group. Full article

(This article belongs to the Topic Organocatalysis and Transition-Metal Catalysis: Key Trends in Synthetic Chemistry and Challenges)

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Supplementary material:
Supplementary File 1 (PDF, 924 KiB)
Supplementary File 2 (MOL, 3 KiB)
Supplementary File 3 (INCHI, 863 B)
Supplementary File 4 (MOL, 3 KiB)

6 pages, 1117 KiB  

Open AccessShort Note

Diethyl(benzamido(diisopropoxyphosphoryl)methyl) phosphonate

by Adrián López-Francés, Francisco Palacios, Aitor Maestro and Javier Vicario

Molbank 2022, 2022(3), M1424; https://doi.org/10.3390/M1424 - 11 Aug 2022

Viewed by 2157

Abstract

Bisphosphonates are widely used in medicine and related areas, mainly for the treatment of bone diseases, such as osteoporosis. However, their synthesis is usually performed under harsh reaction conditions. In order to overcome this limitation, the present work illustrates a new synthetic route [...] Read more.

Bisphosphonates are widely used in medicine and related areas, mainly for the treatment of bone diseases, such as osteoporosis. However, their synthesis is usually performed under harsh reaction conditions. In order to overcome this limitation, the present work illustrates a new synthetic route to access the title α-aminobisphosphonate in milder reaction conditions using α-phosphorylated imines as key intermediates. Full article

(This article belongs to the Topic Organocatalysis and Transition-Metal Catalysis: Key Trends in Synthetic Chemistry and Challenges)

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15 pages, 4920 KiB  

Open AccessReview

Different Chiral Ligands Assisted Enantioselective C-H Functionalization with Transition-Metal Catalysts

by Jian-Zhen Lv, Yue-Ting Wei, Li-Yan Yang, Deng-Feng Yang and Hong-Liang Li

Catalysts 2022, 12(5), 537; https://doi.org/10.3390/catal12050537 - 13 May 2022

Cited by 3 | Viewed by 3383

Abstract

C–H bonds are common in organic molecules, and the functionalization of these inactive C–H bonds has become one of the most powerful methods used to assemble complicated bioactive molecules from readily available starting materials. However, a central challenge in these reactions is controlling [...] Read more.

C–H bonds are common in organic molecules, and the functionalization of these inactive C–H bonds has become one of the most powerful methods used to assemble complicated bioactive molecules from readily available starting materials. However, a central challenge in these reactions is controlling their stereoselectivity. Recently, significant progress has been made in the development of enantioselective C–H activation enabled by different chiral ligands for the formation of C–C and C–X bonds bearing a chiral center. In this paper, we focus on some archetypal chiral ligands for enantioselective C–H functionalization developed in recent years and analyze the mechanism of these methods, aiming to accelerate related research and to search for more efficient strategies. Full article

(This article belongs to the Topic Organocatalysis and Transition-Metal Catalysis: Key Trends in Synthetic Chemistry and Challenges)

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