Palladium-catalyzed [4 + 3] dearomatizing cycloaddition reaction of N-iminoquinolinium ylides

2020 ◽  
Vol 7 (18) ◽  
pp. 2612-2617
Author(s):  
Wenhao Dai ◽  
Chunpu Li ◽  
Yichu Liu ◽  
Xu Han ◽  
Xingjun Li ◽  
...  
Keyword(s):  
Functional Group ◽  
Cycloaddition Reaction ◽  
Membered Ring ◽  
Efficient Approach ◽  
Mild Conditions ◽  
Palladium Catalyzed

An efficient approach to obtain saturated seven-membered ring containing three heteroatoms has been developed by using a palladium-catalyzed [4 + 3] dearomatizing cycloaddition. This approach features mild conditions and good functional group tolerance.

scholarly journals Application of One-Pot Three-Component Condensation Reaction for the Synthesis of New Organophosphorus–Sulfur Macrocycles

Synlett ◽  
2018 ◽  
Vol 29 (11) ◽  
pp. 1496-1501 ◽  
Author(s):  
J. Woollins ◽  
Guoxiong Hua ◽  
David Cordes ◽  
Alexandra Slawin
Keyword(s):  
Multicomponent Reaction ◽  
Room Temperature ◽  
Condensation Reaction ◽  
Synthesis Method ◽  
Membered Ring ◽  
One Pot ◽  
X Ray ◽  
Efficient Approach ◽  
Mild Conditions ◽  
Sulfur Heterocycles

An efficient approach has been developed for the synthesis of new phosphorus–sulfur heterocycles by a one-pot three-component condensation reaction of a four-membered-ring thionation reagent [Lawesson’s reagent or its ferrocene analogue (2,4-diferrocenyl-1,3,2,4-diathiadiphosphetane 2,4-disulfide)], an alkane- or arenedithiol, and a dihaloalkane at room temperature in the presence of triethylamine. The simple synthesis method with mild conditions (room temperature and normal reactant concentrations) enhances further the application of the multicomponent reaction in the preparation of novel phosphorus–sulfur heterocycles. Six representative X-ray structures confirmed the formation of these macrocycles.

scholarly journals Palladium-Catalyzed Cross-Coupling of Gem-Bromofluoroalkenes with Alkylboronic Acids for the Synthesis of Alkylated Monofluoroalkenes

Molecules ◽  
2020 ◽  
Vol 25 (23) ◽  
pp. 5532
Author(s):  
Laëtitia Chausset-Boissarie ◽  
Nicolas Cheval ◽  
Christian Rolando
Keyword(s):  
Organic Synthesis ◽  
Functional Group ◽  
Materials Science ◽  
Cross Coupling ◽  
High Yield ◽  
Efficient Synthesis ◽  
Mild Conditions ◽  
Wide Range ◽  
Palladium Catalyzed ◽  
Novel Strategy

Monofluoroalkenes are versatile fluorinated synthons in organic synthesis, medicinal chemistry and materials science. In light of the importance of alkyl-substituted monofluoroalkenes efficient synthesis of these moieties still represents a synthetic challenge. Herein, we described a mild and efficient methodology to obtain monofluoroalkenes through a stereospecific palladium-catalyzed alkylation of gem-bromofluoroalkenes with primary and strained secondary alkylboronic acids under mild conditions. This novel strategy gives access to a wide range of functionalized tri- and tetrasubstituted monofluoroalkenes in high yield, with good functional group tolerance, independently from the gem-bromofluoroalkenes geometry.

Pd-Catalyzed diastereoselective [3 + 2] cycloaddition of vinylcyclopropanes with sulfamate-derived cyclic imines

2018 ◽  
Vol 16 (26) ◽  
pp. 4881-4887 ◽  
Author(s):  
Qijun Wang ◽  
Chang Wang ◽  
Wangyu Shi ◽  
Yumei Xiao ◽  
Hongchao Guo
Keyword(s):  
Cycloaddition Reaction ◽  
Mild Conditions ◽  
Palladium Catalyzed

The palladium-catalyzed diastereoselective [3 + 2] cycloaddition reaction of vinylcyclopropanes with sulfamate-derived cyclic imines worked efficiently under mild conditions, providing sulfamate-fused pyrrolidines in good to excellent yields.

scholarly journals (4+3)-cycloaddition chemists of oxidopyridinium ions and related study

2019 ◽  
Author(s):  
◽  
Chencheng Fu
Keyword(s):  
Uv Radiation ◽  
Photochemical Reaction ◽  
Functional Group ◽  
Cycloaddition Reaction ◽  
Product Yield ◽  
Membered Ring ◽  
Starting Material ◽  
Unsaturated Ester ◽  
Rapid Access ◽  
Cyclobutane Ring

The (4+3)-cycloaddition reaction is a cycloaddition between a 4-atom species and a 3-atom species to form a seven-membered ring. This reaction results in the formation of seven-membered rings. Our research expanded the scope of (4+3)-cycloaddition reaction by using the oxidopyridinium species as the dienophile -- the 3-atom species. By adding an electron-withdrawing functional group to the starting material, we were be able to get good to excellent product yield. The process provides rapid access to bicyclic nitrogenous structures resembling natural alkaloids. [2+2]-Photocycloaddition is a cycloaddition between two olefins to form a cyclobutane ring. The intramolecular [2+2]-cycloaddition of nitrogen-substituted alkenes can be employed to make complicated alkaloids. Our previous work made the 7-azabicyclo[4.3.1]deca-3,8-diene skeleton, which is a nice substrate for the cycloaddition. Under UV radiation, the heteroatom-substituted unsaturated ester undergoes intramolecular [2+2]-cycloaddition with the cyclic alkene to make a cage-like ketone in good to excellent yield, giving rise to a rigid tropane-like alkaloid skeleton. The scope and mechanism of the photochemical reaction will be discussed.

scholarly journals Palladium Catalyzed α,β-Homodiarylation of Vinyl Esters in Aqueous Medium

2021 ◽  
Author(s):  
Ryszard Ostaszewski ◽  
Damian Trzepizur ◽  
Anna Brodzka ◽  
Dominik Koszelewski ◽  
Monika Wilk
Keyword(s):  
Catalytic Activity ◽  
Functional Group ◽  
Reaction Medium ◽  
Environmentally Benign ◽  
Vinyl Esters ◽  
Arylboronic Acid ◽  
Reaction Conditions ◽  
Mild Conditions ◽  
Palladium Catalyzed ◽  
One Step

Abstract A palladium catalyzed 1,2-diarylation of vinyl esters with sustainable arylbornic acids in water has been developed. This newly elaborated protocol features good functional group tolerance and provides a one-step access to 1,2-diaryletahol derivatives under mild reaction conditions. The presented reaction can be carried out in water smoothly without the addition of any ligands at ambient temperature what makes this procedure environmentally benign. The transformation occurs within a single catalytic cycle and is feasible due to the modification of transition metal catalytic activity through the influence of π-acceptor olefin (benzoquinone) as well as the polar protic reaction medium (water in particular). Moreover, the protocol allows to generate entire compounds libraries (highly profitable in medicinal chemistry) and utilizes sustainable arylboronic acid as coupling partners under mild conditions.

scholarly journals (4+3)-Cycloaddition of Donor-Acceptor Cyclopropanes with Thiochalcones: A Diastereoselective Access to Tetrahydrothiepines

2019 ◽  
Author(s):  
André U. Augustin ◽  
J. Luca Merz ◽  
Peter G. Jones ◽  
Grzegorz Mloston ◽  
Daniel Werz
Keyword(s):  
Lewis Acid ◽  
Functional Group ◽  
Cycloaddition Reaction ◽  
Building Blocks ◽  
Mild Conditions ◽  
Donor Acceptor ◽  
Acid Catalyzed ◽  
Sulfur Containing

A general approach is described for the formation of tetrahydrothiepines using donor-acceptor cyclopropanes. Thiochalcones, functioning as sulfur-containing four-atom building blocks, were reacted in a Lewis-acid-catalyzed formal (4+3)-cycloaddition reaction with donor-acceptor cyclopropanes as three-atom building blocks. Under mild conditions various tetrahydrothiepines were synthesized in good yields in a stereosepecific reaction with high functional group tolerance.

Synthesis of Phenanthrenes via Palladium-Catalyzed Three-Component Domino Reaction of Aryl Iodides, Internal Alkynes, and o-Bromobenzoic Acids

Synthesis ◽  
2019 ◽  
Vol 52 (08) ◽  
pp. 1223-1230 ◽  
Author(s):  
Yuzhong Yang ◽  
Liwei Zhou ◽  
Xiumei Yang ◽  
Xiai Luo ◽  
Guobo Deng ◽  
...  
Keyword(s):  
Functional Group ◽  
Domino Reaction ◽  
Efficient Approach ◽  
Aryl Iodides ◽  
Internal Alkynes ◽  
Palladium Catalyzed ◽  
Alkyne Insertion ◽  
Three Component Coupling

A new palladium-catalyzed domino alkyne insertion/C–H activation/decarboxylation sequence has been developed, which provides an efficient approach for synthesizing a variety of functionalized phenanthrenes in moderate to good yields. The method shows broad substrate scope and good functional group tolerance by employing readily available materials, including aryl iodides, internal alkynes, and o-bromobenzoic acids, as three-component coupling partners.

scholarly journals (4+3)-Cycloaddition of Donor-Acceptor Cyclopropanes with Thiochalcones: A Diastereoselective Access to Tetrahydrothiepines

2019 ◽  
Author(s):  
André U. Augustin ◽  
J. Luca Merz ◽  
Peter G. Jones ◽  
Grzegorz Mloston ◽  
Daniel Werz
Keyword(s):  
Lewis Acid ◽  
Functional Group ◽  
Cycloaddition Reaction ◽  
Building Blocks ◽  
Mild Conditions ◽  
Donor Acceptor ◽  
Acid Catalyzed ◽  
Sulfur Containing

A general approach is described for the formation of tetrahydrothiepines using donor-acceptor cyclopropanes. Thiochalcones, functioning as sulfur-containing four-atom building blocks, were reacted in a Lewis-acid-catalyzed formal (4+3)-cycloaddition reaction with donor-acceptor cyclopropanes as three-atom building blocks. Under mild conditions various tetrahydrothiepines were synthesized in good yields in a stereosepecific reaction with high functional group tolerance.

Diastereoselective Palladium-Catalyzed [4+1] Cycloadditions of Vinyl Benzoxazinanones with in situ Formed Carbenes

Synthesis ◽  
2021 ◽  
Author(s):  
Yanhua Ma ◽  
Fanxiao Meng ◽  
Ruonan Wang ◽  
Yaxin Fan ◽  
Qinqiang Su ◽  
...  
Keyword(s):  
Functional Group ◽  
Quinone Methides ◽  
Nucleophilic Carbenes ◽  
Mild Conditions ◽  
Palladium Catalyzed

Herein, we present a palladium-catalyzed tandem [4+1] cycloadditions of vinyl benzoxazinanones with N-tosylhydrazones. The cycloaddition is accomplished by merging the in situ generated aza-ortho-quinone methides (aza-o-QMs) with nucleophilic carbenes. This method enables the construction of diverse indolines with broad functional group compatibility in good yields with high levels of diastereoselectivity under mild conditions.

Dual Nickel/Palladium-Catalyzed Reductive Cross-Coupling Reactions Between Two Phenol Derivatives

2020 ◽  
Author(s):  
Baojian Xiong ◽  
Yue Li ◽  
Yin Wei ◽  
Søren Kramer ◽  
Zhong Lian
Keyword(s):  
Functional Group ◽  
Low Cost ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Phenol Derivatives ◽  
Cross Coupling Reactions ◽  
Palladium Catalyzed ◽  
One Step ◽  
Aryl Tosylates ◽  
Low Sensitivity

Cross-coupling between substrates that can be easily derived from phenols is highly attractive due to the abundance and low cost of phenols. Here, we report a dual nickel/palladium-catalyzed reductive cross-coupling between aryl tosylates and aryl triflates; both substrates can be accessed in just one step from readily available phenols. The reaction has a broad functional group tolerance and substrate scope (>60 examples). Furthermore, it displays low sensitivity to steric effects demonstrated by the synthesis of a 2,2’disubstituted biaryl and a fully substituted aryl product. The widespread presence of phenols in natural products and pharmaceuticals allow for straightforward late-stage functionalization, illustrated with examples such as Ezetimibe and tyrosine. NMR spectroscopy and DFT calculations indicate that the nickel catalyst is responsible for activating the aryl triflate, while the palladium catalyst preferentially reacts with the aryl tosylate.

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