Visible-light-mediated borylation of aryl and alkyl halides with a palladium complex

2020 ◽  
Vol 18 (23) ◽  
pp. 4390-4394
Author(s):  
Jia-Hui Zhao ◽  
Zhao-Zhao Zhou ◽  
Yue Zhang ◽  
Xuan Su ◽  
Xi-Meng Chen ◽  
...  
Keyword(s):  
Visible Light ◽  
Functional Group ◽  
Palladium Complex ◽  
Alkyl Halides ◽  
Palladium Catalyzed ◽  
High Yields

Palladium catalyzed visible-light-mediated borylation of inactivated aryl and alkyl halides is reported; the method provided high yields and excellent functional group compatibility.

scholarly journals Palladium-catalyzed hydroalkylation of methylenecyclopropanes with simple hydrazones

2020 ◽  
Vol 11 (39) ◽  
pp. 10759-10763
Author(s):  
Jinzhong Yao ◽  
Zhangpei Chen ◽  
Lin Yu ◽  
Leiyang Lv ◽  
Dawei Cao ◽  
...  
Keyword(s):  
Functional Group ◽  
Bond Scission ◽  
Terminal Alkenes ◽  
Palladium Catalyzed ◽  
High Yields

A palladium-catalyzed hydroalkylation of methylenecyclopropanes via selective C–C σ-bond scission was achieved, in which simple hydrazones served as carbanion equivalents. This method affords high yields of C-alkylated terminal alkenes with good functional group compatibility.

scholarly journals Tyrosine and Drug-like Late-stage Benzylic Functionalization via Photoredox Catalysis

2020 ◽  
Author(s):  
Tobias Brandhofer ◽  
Volker Derdau ◽  
María Mendez ◽  
Christoph Pöverlein ◽  
Olga Garcia Mancheno
Keyword(s):  
Natural Products ◽  
Visible Light ◽  
Late Stage ◽  
Medicinal Chemistry ◽  
Functional Group ◽  
Reaction Conditions ◽  
Site Selectivity ◽  
Wide Range ◽  
High Yields ◽  
Therapeutic Compounds

Abstract Visible light mediated late-stage functionalization is a rising field in synthetic and medicinal chemistry, allowing the fast and diversified modification of valuable, potentially therapeutic compounds such as peptides. However, there are relatively few mild methodologies for the C(sp3)-H functionalization of complex peptides. Herein, we report a visible light mediated photocatalytic protocol for the benzylic C-H modification of tyrosine and related C-H bonds. The embraced radical-cation/deprotonation strategy enables an incorporation of a wide range of valuable functional groups in high yields and chemoselectivity. The mild reaction conditions, site-selectivity and high functional group tolerance was highlighted by the functionalization of complex peptides, drugs and natural products, providing a promising synthetic platform in medicinal chemistry.

Recyclable Heterogeneous Palladium-Catalyzed Carbonylative Cyclization of 2-Iodoanilines with Aryl Iodides Leading to 2-Arylbenzoxazinones

Synthesis ◽  
2019 ◽  
Vol 52 (04) ◽  
pp. 581-590 ◽  
Author(s):  
Zhaotao Xu ◽  
Bin Huang ◽  
Zebiao Zhou ◽  
Mingzhong Cai
Keyword(s):  
Carbon Monoxide ◽  
Palladium Catalyst ◽  
Functional Group ◽  
Atom Economy ◽  
Highly Efficient ◽  
Aryl Iodides ◽  
Palladium Catalyzed ◽  
High Yields

A highly efficient and practical heterogeneous palladium-catalyzed carbonylative coupling of 2-iodoanilines with aryl iodides has been developed. The reaction occurs smoothly in toluene at 110 °C with N,N-diisopropylethylamine as base under carbon monoxide (5 bar) and offers a general and powerful tool for the construction of various valuable 2-arylbenzoxazinones with excellent atom-economy, high functional group tolerance, good to high yields, and easy recyclability of the palladium catalyst. The reaction is the first example of heterogeneous palladium-catalyzed carbonylative coupling for the preparation of diverse 2-arylbenzoxazinones from commercially easily available 2-iodoanilines and aryl iodides.

Visible-Light-Driven Phosphonoalkylation of Alkenes

Synlett ◽  
2021 ◽  
Vol 32 (04) ◽  
pp. 378-382
Author(s):  
Yue-Ming Jiang ◽  
Jie Liu ◽  
Qiang Fu ◽  
Yu-Ming Yu ◽  
Da-Gang Yu
Keyword(s):  
Transition Metal ◽  
Visible Light ◽  
Functional Group ◽  
Reaction Conditions ◽  
Metal Free ◽  
Alkyl Sulfonates ◽  
Visible Light Driven ◽  
High Yields

AbstractPhosphonylation of alkenes is important for the generation of valuable organophosphines. However, redox-neutral difunctionalization of alkenes with readily available H-P(O) compounds remains underdeveloped. Herein, we report the first visible-light-driven redox-neutral phosphonoalkylation of alkenes. A variety of organophosphorus-containing three-membered carbocyclic scaffolds are synthesized from alkene-bearing alkyl sulfonates with H-P(O) compounds. The transition-metal-free protocol displays good functional group tolerance, broad substrate scope, high yields, and mild reaction conditions.

Photocatalytic hydrogenation of nitroarenes: supporting effect of CoOx on TiO2 nanoparticles

2019 ◽  
Vol 43 (2) ◽  
pp. 748-754 ◽  
Author(s):  
Srinivasa Rao Amanchi ◽  
K. V. Ashok Kumar ◽  
Bhairi Lakshminarayana ◽  
G. Satyanarayana ◽  
Ch. Subrahmanyam
Keyword(s):  
Solid State ◽  
Visible Light ◽  
Tio2 Nanoparticles ◽  
Visible Light Irradiation ◽  
Functional Group ◽  
Synthesis Method ◽  
Light Irradiation ◽  
Supporting Effect ◽  
High Yields ◽  
Solid State Synthesis Method

We report a nanocatalyst CoOx/TiO2 with different loadings of CoOx by a solid state synthesis method for the green hydrogenation of nitroarenes under visible light irradiation. Notably, we observed very good selectivity, conversion and functional group tolerance with high yields.

scholarly journals Correction: Visible-light-mediated borylation of aryl and alkyl halides with a palladium complex

2021 ◽  
Author(s):  
Jia-Hui Zhao ◽  
Zhao-Zhao Zhou ◽  
Yue Zhang ◽  
Xuan Su ◽  
Xi-Meng Chen ◽  
...  
Keyword(s):  
Visible Light ◽  
Palladium Complex ◽  
Alkyl Halides

Correction for ‘Visible-light-mediated borylation of aryl and alkyl halides with a palladium complex’ by Jia-Hui Zhao, et al., Org. Biomol. Chem., 2020, 18, 4390–4394, DOI: 10.1039/D0OB00028K.

Palladium-Catalyzed Allylation of Polyfluoroarenes with Allylic Pivalates

Synlett ◽  
2017 ◽  
Vol 29 (02) ◽  
pp. 251-255
Author(s):  
Xinpeng Jiang ◽  
Yong Liu ◽  
Lei Zhang ◽  
Jinkang Chen ◽  
Kang Cheng ◽  
...  
Keyword(s):  
Catalytic System ◽  
Good Yield ◽  
Functional Group ◽  
Palladium Complex ◽  
Oxidative Addition ◽  
Reductive Elimination ◽  
Nucleophilic Attack ◽  
Palladium Catalyzed ◽  
Mechanistic Investigations

An efficient 1,5-cyclooctadiene–PdCl2/dicyclohexyl(2′,4′,6′-triisopropylbiphenyl-2-yl)phosphine (XPhos) catalytic system was developed for C–H allylation of polyfluoroarenes with allylic pivalates. The reactions showed excellent functional-group tolerance, good yields, and high regioselectivities. Mechanistic investigations supported a (π-allyl)palladium complex pathway through a directed oxidative addition of the allylic pivalate to palladium, followed by sequential nucleophilic attack by the polyfluorobenzene and reductive elimination. In a gram-scale reaction, a palladium loading of 0.5 mol% was enough to afford the required product in good yield.

Arylation of Amide and Urea C(sp3)–H Bonds with Aryl Tosylates Generated In Situ from Phenols

Synlett ◽  
2017 ◽  
Vol 28 (19) ◽  
pp. 2581-2586 ◽  
Author(s):  
Wen-Jun Zhou ◽  
Da-Gang Yu ◽  
Yong-Yuan Gui ◽  
Xiao-Wang Chen
Keyword(s):  
Hydrogen Atom ◽  
Visible Light ◽  
Room Temperature ◽  
Functional Group ◽  
Hydrogen Atom Transfer ◽  
Nickel Catalysis ◽  
Direct Transformation ◽  
Aryl Tosylates ◽  
High Yields

The arylation of amide and urea C(sp3)–H bonds with aryl tosylates generated in situ from phenols has been realized at room temperature by combining visible-light-photoredox catalysis, hydrogen-atom-transfer catalysis, and nickel catalysis. This streamlined protocol permits rapid functionalization of phenols and direct transformation of α-amino C(sp3)–H bonds. The C(sp3)–H arylation products are obtained in high yields with good functional-group tolerance at low catalyst loadings.

scholarly journals Advancements in Visible-Light-Enabled Radical C(sp)2–H Alkylation of (Hetero)arenes

Synthesis ◽  
2019 ◽  
Vol 51 (05) ◽  
pp. 1063-1072 ◽  
Author(s):  
Alexandra Sun ◽  
Rory McAtee ◽  
Edward McClain ◽  
Corey Stephenson
Keyword(s):  
Carboxylic Acid ◽  
Visible Light ◽  
Alkyl Radical ◽  
Functional Group ◽  
Short Review ◽  
Alkyl Halides ◽  
Research Development ◽  
Visible Light Driven ◽  
Radical Generation ◽  
Operational Simplicity

The Minisci reaction, which encompasses the radical C–H alkylation of heteroarenes, has undergone revolutionary development in recent years. The application of photoredox catalysis to alkyl radical generation has given rise to a multitude of methods that feature enhanced functional group tolerance, generality, and operational simplicity. The intent of this short review is to bring readers up to date on this rapidly expanding field. Specifically, we will highlight key examples of visible-light-driven Minisci alkylation strategies that represent key advancements in this area of research. The scope and limitations of these transformations will be discussed, with a focus on examining the underlying pathways for alkyl radical generation. Our goal is to make this short review a stepping stone for further synthetic research development. Sections are organized based on alkyl radical precursor reagents.1 Introduction2 Alkyl Carboxylic Acids and Carboxylic Acid Derivatives3 Alkylboronic Acids4 Potassium Alkyl- and Alkoxymethyltrifluoroborates5 Alkyl Halides6 Alcohols and Ethers7 Conclusion

Visible-light-mediated hydrodehalogenation and Br/D exchange of inactivated aryl and alkyl halides with a palladium complex

2019 ◽  
Vol 6 (10) ◽  
pp. 1649-1654 ◽  
Author(s):  
Zhao-Zhao Zhou ◽  
Jia-Hui Zhao ◽  
Xue-Ya Gou ◽  
Xi-Meng Chen ◽  
Yong-Min Liang
Keyword(s):  
Visible Light ◽  
Palladium Complex ◽  
Radical Addition ◽  
Alkyl Halides ◽  
Reductive Dehalogenation ◽  
Reductive Cyclization ◽  
Alkyl Bromides

Photo-induced radical reductive dehalogenation of inactivated aryl/alkyl bromides and chlorides with a palladium complex is described. Reductive cyclization, dehalogenative deuteration, and radical addition process can be achieved smoothly.

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