Silver-Promoted Versatile Cross-Dehydrogenative Coupling of Quinaldine with Usual Ethers

Synlett ◽  
2019 ◽  
Vol 30 (18) ◽  
pp. 2096-2100 ◽  
Author(s):  
Shoufeng Wang ◽  
Yafei Fan ◽  
Huaiqing Zhao ◽  
Jianfeng Wang ◽  
Shuxiang Zhang ◽  
...  
Keyword(s):  
Small Molecules ◽  
Functional Groups ◽  
Dehydrogenative Coupling ◽  
Convenient Route

The application of small molecules as synthetic blocks is a field of great meaning and full of challenges, especially the use of inert ether molecules, such as THF as starting materials. A versatile and easily handled cross-dehydrogenative coupling between ethers and quinaldine is reported here. Compared to the developed reaction, Selectfluor is used as a mild oxidant, and a variety of functional groups are tolerated. Nitrogen protection, anhydrous systems, and external base are not needed, making this method a convenient route to functional heterocycles.

Broad Assessment of Bioactivity of a Collection of Spiroindane Pyrrolidines Through “Cell Painting”

2020 ◽  
Author(s):  
Zarko Boskovic ◽  
Manvendra Singh ◽  
Zachary Pearson ◽  
Nathan Garza
Keyword(s):  
Biological Activity ◽  
Small Molecules ◽  
Functional Groups ◽  
Organelle Morphology

A collection of small molecules has been synthesized by composing photo-cycloaddition, C-H functionalization, and N-capping strategies. Multidimensional biological fingerprints of molecules comprising this collection have been recorded as changes in cell and organelle morphology. This untargeted, phenotypic approach allowed for a broad assessment of biological activity to be determined. Reproducibility and the magnitude of measured fingerprints revealed activity of several treatments. Reactive functional groups, such as imines, dominated the observed activity. Two non-reactive candidate compounds with distinct bioactivity fingerprints were identified, as well.

Nanogold(0)-Catalyzed Addition of Heteroelement σ Linkages to Functional Groups

Synthesis ◽  
2019 ◽  
Vol 51 (12) ◽  
pp. 2435-2454 ◽  
Author(s):  
Manolis Stratakis ◽  
Ioannis N. Lykakis
Keyword(s):  
Functional Groups ◽  
Carbonyl Compounds ◽  
Au Nanoparticles ◽  
Future Perspectives ◽  
Metal Catalysis ◽  
Dehydrogenative Coupling ◽  
Catalytic Sites ◽  
Diazo Carbonyl Compounds ◽  
Aromatic Carbonyl Compounds ◽  
Subsequent Addition

In recent years, supported Au nanoparticles and nanoporous Au materials have shown remarkable catalytic activity in the activation of σ heteroelement linkages such as, Si–H, Si–Si, B–B and B–Si, and their subsequent addition to functional groups, primarily π bonds. In this review article we discuss the reaction modes known to date, and attempt to discuss the mechanistic clues of these transformations which are rather unexpected in terms of conventional transition-metal catalysis concepts, given that the catalytic sites are metallic Au(0).1 Introduction2 Activation of Hydrosilanes2.1 Reactions of Hydrosilanes with Alkynes2.1.1 Hydrosilylation2.1.2 Dehydrogenative Coupling2.2 Reactions of Hydrosilanes with Allenes2.3 Reactions of Hydrosilanes with Carbonyl Compounds and Imines2.4 Reactions of Hydrosilanes with α-Diazo Carbonyl Compounds2.5 Miscellaneous Transformations from the Nano Au-Catalyzed Activation­ of Hydrosilanes3 Activation of Disilanes3.1 Disilylation of Alkynes3.2 Reactions of 1,1,2,2-Tetramethyldisilane with Alkynes4 Activation of Diboranes4.1 Diborylation of Alkenes4.2 Diborylation of Alkynes4.3 Diborylation of Allenes4.4 Diborylation of Methylenecyclopropanes5 Activation of Silylboranes5.1 Silaboration of Alkynes5.2 Silaboration of Allenes5.3 Silaboration of Unactivated Epoxides and Oxetanes5.4 Reactions of Silylboranes with Aromatic Carbonyl Compounds6 Conclusions and Future Perspectives

scholarly journals Reactivity of Copper Electrodes towards Functional Groups and Small Molecules in the Context of CO2 Electro-Reductions

Catalysts ◽  
2017 ◽  
Vol 7 (5) ◽  
pp. 161 ◽  
Author(s):  
Bernhard Schmid ◽  
Christian Reller ◽  
Sebastian Neubauer ◽  
Maximilian Fleischer ◽  
Romano Dorta ◽  
...  
Keyword(s):  
Small Molecules ◽  
Functional Groups ◽  
Copper Electrodes

Broad Assessment of Bioactivity of a Collection of Spiroindane Pyrrolidines Through “Cell Painting”

2020 ◽  
Author(s):  
Zarko Boskovic ◽  
Manvendra Singh ◽  
Zachary Pearson ◽  
Nathan Garza
Keyword(s):  
Biological Activity ◽  
Small Molecules ◽  
Functional Groups ◽  
Organelle Morphology

A collection of small molecules has been synthesized by composing photo-cycloaddition, C-H functionalization, and N-capping strategies. Multidimensional biological fingerprints of molecules comprising this collection have been recorded as changes in cell and organelle morphology. This untargeted, phenotypic approach allowed for a broad assessment of biological activity to be determined. Reproducibility and the magnitude of measured fingerprints revealed activity of several treatments. Reactive functional groups, such as imines, dominated the observed activity. Two non-reactive candidate compounds with distinct bioactivity fingerprints were identified, as well.

scholarly journals Harnessing the Intrinsic Photochemistry of Isoxazoles for the Development of Chemoproteomic Crosslinking Methods

2021 ◽  
Author(s):  
Marshall G. Lougee ◽  
Vinayak Vishnu Pagar ◽  
Hee Jong Kim ◽  
Samantha X. Pancoe ◽  
Robert H. Mach ◽  
...  
Keyword(s):  
Protein Binding ◽  
Small Molecules ◽  
Functional Groups ◽  
Ex Vivo ◽  
Initial Report ◽  
Biologically Relevant ◽  
Fine Grained ◽  
Wide Range ◽  
Unique Method

Photo-crosslinking is a powerful technique for identifying both coarse- and fine-grained information on protein binding by small molecules. However, the scope of useful functional groups remains limited, with most studies focusing on diazirine, aryl azide, or benzophenone-containing molecules. Here, we report a unique method for photo-crosslinking, employing the intrinsic photochemistry of the isoxazole, a common heterocycle in medicinal chemistry, to offer an alternative to existing strategies using more perturbing, extrinsic crosslinkers. In this initial report, this technique is applied both in vitro and ex vivo, used in a variety of common chemoproteomic workflows, and validated across multiple proteins, demonstrating the utility of isoxazole photo-crosslinking in a wide range of biologically relevant experiments.

Synthesis of star-shaped small molecules carrying peripheral 1,8-naphthalimide functional groups and their applications in organic solar cells

2015 ◽  
Vol 115 ◽  
pp. 181-189 ◽  
Author(s):  
Jicheng Zhang ◽  
Guangwu Li ◽  
Chong Kang ◽  
Heng Lu ◽  
Xiuxiu Zhao ◽  
...  
Keyword(s):  
Solar Cells ◽  
Small Molecules ◽  
Functional Groups ◽  
Organic Solar Cells

High adsorption performance polymers modified by small molecules containing functional groups for CO2separation

RSC Advances ◽  
2013 ◽  
Vol 3 (1) ◽  
pp. 50-54 ◽  
Author(s):  
Zhihua Qiao ◽  
Zhi Wang ◽  
Song Zhao ◽  
Shuangjie Yuan ◽  
Jixiao Wang ◽  
...  
Keyword(s):  
Small Molecules ◽  
Functional Groups ◽  
High Adsorption ◽  
Adsorption Performance

A Highly Efficient Copper(II)-Catalyzed Cross-Dehydrogenative-Coupling Reaction of N-Arylglycine Esters with 2-Arylimidazo[1,2-a]pyridines

Synthesis ◽  
2018 ◽  
Vol 50 (14) ◽  
pp. 2775-2783 ◽  
Author(s):  
Zhi-Qiang Zhu ◽  
Zhang-Gao Le ◽  
Li-Jin Xiao ◽  
Ying Chen ◽  
Zong-Bo Xie ◽  
...  
Keyword(s):  
Amino Acid ◽  
Functional Groups ◽  
Coupling Reaction ◽  
Amino Acid Esters ◽  
Synthetic Method ◽  
Reaction Conditions ◽  
Highly Efficient ◽  
Dehydrogenative Coupling ◽  
High Yields ◽  
Acid Esters

A rapid and highly efficient copper(II)-catalyzed cross-dehydrogenative coupling (CDC) reaction of N-arylglycine esters with imidazo[1,2-a]pyridines has been described. A broad range of N-arylglycine esters underwent the CDC reaction smoothly with 2-arylimidazo[1,2-a]pyridines to give α-substituted α-amino acid esters in excellent yields. This synthetic method has the advantages of high yields, good functional groups compatibility, simple operation, and mild reaction conditions. A possible mechanism for the CDC reaction is also proposed. The use of a copper salt as the catalyst and air as the terminal oxidant makes this transformation sustainable and practical.

scholarly journals Synthesis of highly substituted fluorenones via metal-free TBHP-promoted oxidative cyclization of 2-(aminomethyl)biphenyls. Application to the total synthesis of nobilone

2021 ◽  
Vol 17 ◽  
pp. 2668-2679
Author(s):  
Ilya A P Jourjine ◽  
Lukas Zeisel ◽  
Jürgen Krauß ◽  
Franz Bracher
Keyword(s):  
Total Synthesis ◽  
Natural Product ◽  
Functional Groups ◽  
Oxidative Cyclization ◽  
Metal Free ◽  
Dehydrogenative Coupling ◽  
Protective Groups

Highly substituted fluorenones are readily prepared in mostly fair to good yields via metal- and additive-free TBHP-promoted cross-dehydrogenative coupling (CDC) of readily accessible N-methyl-2-(aminomethyl)biphenyls and 2-(aminomethyl)biphenyls. This methodology is compatible with numerous functional groups (methoxy, cyano, nitro, chloro, and SEM and TBS-protective groups for phenols) and was further utilized in the first total synthesis of the natural product nobilone.

Sign in / Sign up

Export Citation Format

Share Document