Article
Chemistry, Multidisciplinary
Ling Yang, Dong-Hang Tan, Wen-Xin Fan, Xu-Ge Liu, Jia-Qiang Wu, Zhi-Shu Huang, Qingjiang Li, Honggen Wang
Summary: A new method was proposed utilizing benzyl N-methyliminodiacetyl (MIDA) boronates for photochemical radical C-H halogenation, enabling successful fluorination, chlorination, and bromination reactions. The resulting brominated product could be further transformed into a variety of organic compounds, including those difficult to form with alpha-halo sp(2)-B boronate esters, by reaction with different nucleophiles. An activation effect of the B(MIDA) moiety was discovered.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Inorganic & Nuclear
Ralph W. Adams, Richard O. John, Damir Blazina, Beatriz Eguillor, Martin C. R. Cockett, John P. Dunne, Joaquin Lopez-Serrano, Simon B. Duckett
Summary: This article describes the thermal and photochemical reactions of Ru metal complexes with H-2 and diphenylacetylene. The reactions were monitored and validated using various techniques including NMR spectroscopy. The results show that the reaction mechanisms and products vary with different complexes and reaction conditions.
EUROPEAN JOURNAL OF INORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Anna Garbagnati, Michael Seidl, Gabor Balazs, Manfred Scheer
Summary: The study investigated the oxidation reactions of a compound with halogens or halogen sources under different conditions, and characterized the products using various experimental methods, as well as analyzed their electronic structures.
CHEMISTRY-A EUROPEAN JOURNAL
(2022)
Article
Chemistry, Organic
Partha Pratim Sen, Vishal Jyoti Roy, Sudipta Raha Roy
Summary: An atom economic method using noncovalent interactions to trigger paired electrolysis for bromination reactions is demonstrated. This mild and efficient electrochemical protocol allows the activation of C(sp(3))-Br bonds in organic-bromo derivatives, leading to the synthesis of aromatic compounds as well as useful byproducts.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Lilla G. Gombos, Leo Werner, Dieter Schollmeyer, Carlos A. Martinez-Huitle, Siegfried R. Waldvogel
Summary: A simple electrochemical protocol has been developed for the selective alkene dibromination of naturally derived olefins. This protocol avoids the use of hazardous Br-2 or its analogues by utilizing readily available, inexpensive, and harmless sodium bromide as a reagent and supporting electrolyte, along with sustainable carbon-based electrodes. The protocol achieves high yields of the desired products and has demonstrated scalability.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Jingjing Wu, Chao Shu, Zhihang Li, Adam Noble, Varinder K. Aggarwal
Summary: This article describes a visible-light photoredox-catalyzed decarboxylative halogenation reaction using inexpensive inorganic halide salts as halogenating agents. Bromination with lithium bromide can be achieved using an organic photoredox catalyst under simple conditions, while chlorination requires dual photoredox-copper catalysis. The reaction exhibits excellent functional group tolerance and can convert structurally complex natural products into alkyl bromides and chlorides. Additionally, the method is also applicable to thiocyanation reactions with potassium thiocyanide for the synthesis of alkyl thiocyanates.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Uwe Osswald, Johannes Boneberg, Valentin Wittmann
Summary: Multivalent receptor-ligand binding is crucial in biological recognition processes. The incorporation of photoswitches into multivalent ligands enables the reversible change of spatial orientation, resulting in altered binding affinity and mode. This study presents a divalent ligand for wheat germ agglutinin (WGA) with an arylazopyrazole photoswitch, showing significant changes in lectin binding affinity and mode.
CHEMISTRY-A EUROPEAN JOURNAL
(2022)
Article
Engineering, Environmental
Andrew W. Psoras, Seth W. McCoy, Keith P. Reber, Daniel L. McCurry, John D. Sivey
Summary: This study examines the influence of ipso substitution on the formation of trihalomethanes (THMs) during water chlorination. It confirms the conversion of C-Br bonds into C-Cl bonds for parabens and salicylates, resulting in the presence of brominated and nonhalogenated precursors, which generate polybrominated THMs. The THM molar yield and bromine incorporation were observed to be higher for brominated precursors compared to nonhalogenated precursors. The impact of ipso substitution on THM formation varies with the structure of the organic precursor.
ENVIRONMENTAL SCIENCE & TECHNOLOGY
(2023)
Article
Chemistry, Applied
Sudip Guria, Constantin G. Daniliuc, Ulrich Hennecke
Summary: Enantioselective iodocycloetherifications can be achieved using sterically highly demanding BINOL-based phosphoric acid diesters as catalyst, requiring cocatalysis by triphenylphosphine selenide. Good to excellent enantioselectivities can be achieved for a broad range of substrates with low catalyst and cocatalyst loadings of 1 mol %. Triphenylphosphine selenide itself does not strongly impact diastereoselectivity, but improves reactivity and enhances enantioselectivity when combined with a BINOL-based phosphoric acid diester.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Review
Biochemistry & Molecular Biology
Truong Giang Luu, Yongju Jung, Hee-Kwon Kim
Summary: This review summarizes recent studies on visible-light-mediated halogenation reactions with photocatalysts, which have improved reaction efficiency, reduced toxicity, and promoted reactions under mild conditions.
Article
Chemistry, Multidisciplinary
Ming-Yu Chen, Sylvain Charvet, Pierre-Adrien Payard, Marie-Eve L. Perrin, Julien C. Vantourout
Summary: A robust electrochemically driven nickel-catalyzed halogen exchange reaction has been reported, allowing the conversion of heavy halogens or polar atoms to lighter and more lipophilic chloride groups to modify properties or block undesired reactivity.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Materials Science, Multidisciplinary
Chang Liu, Jiachuan Hua, Pui Fai Ng, Bin Fei
Summary: Dityrosine crosslinks play a crucial role in enhancing mechanical properties and stability of polymers, commonly found in insects and utilized in new synthetic materials. The photochemical method offers a unique advantage for the formation of dityrosine bonding and may provide novel strategies for photo-activated tyrosine unit manipulation.
JOURNAL OF MATERIALS SCIENCE & TECHNOLOGY
(2021)
Review
Chemistry, Multidisciplinary
Johannes Grosskopf, Thorsten Bach
Summary: Upon irradiation with a suitable chiral catalyst, racemic compounds can be converted into enantiopure compounds through a process called photochemical deracemization. This review comprehensively covers the research and current developments in this field, discussing the reactions and mechanistic details underlying the presented reaction. Photochemical deracemization offers a unique opportunity to directly obtain enantiopure compounds from racemates, and short-lived intermediates play a key role in determining the enantioselectivity.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Multidisciplinary Sciences
Huamin Wang, Huiling Shao, Ankita Das, Subhabrata Dutta, Hok Tsun Chan, Constantin Daniliuc, K. N. Houk, Frank Glorius
Summary: In this study, a photoinduced ring enlargement method of thiophenes was developed, which involves the insertion of bicyclo[1.1.0]butanes to form eight-membered bicyclic rings under mild conditions. The synthetic value, broad functional-group compatibility, and excellent chemo- and regioselectivity were demonstrated by scope evaluation and product derivatization. Experimental and computational studies suggested a photoredox-induced radical pathway.
Article
Chemistry, Multidisciplinary
Yasmine S. Zubi, Bingqing Liu, Yifan Gu, Dipankar Sahoo, Jared C. Lewis
Summary: This study successfully created artificial metalloenzymes (ArMs) by incorporating Ru (II) polypyridyl complexes into a protein scaffold for controlling the properties of photocatalysts in visible light photocatalysis. By engineering modifications, the photophysical properties of ArMs were improved, resulting in higher efficiency compared to Ru(Bpy)(3)(2+) in certain organic transformations.
