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.

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.

Efficient Synthesis of Diverse 5-Thio- or 5-Selenotriazoles: One-Pot Multicomponent Reaction from Elemental Sulfur or Selenium

Synthesis ◽  
2019 ◽  
Vol 51 (22) ◽  
pp. 4170-4182 ◽  
Author(s):  
Lin-Lin Zhang ◽  
Ya-Ting Li ◽  
Ting Gao ◽  
Sha-Sha Guo ◽  
Bei Yang ◽  
...  
Keyword(s):  
Elemental Sulfur ◽  
Functional Group ◽  
High Efficiency ◽  
Efficient Synthesis ◽  
One Pot ◽  
Mild Conditions ◽  
Ligand Free ◽  
Multistep Reaction ◽  
Easy Operation

A sequential multistep reaction toward 5-thio- or 5-selenotriazoles has been established by generation of both copper(I) triazolides and sulfenylating or selenylating agents in situ, starting from elemental sulfur or selenium. This reaction features mild conditions, readily available and broad-scope substrates, good functional group compatibility, high efficiency and regioselectivity, easy operation, and ligand-free CuI.

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.

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.

Palladium-Catalyzed Synthesis of Aryl and Heteroaryl Difluoromethylated Phosphonates

Synthesis ◽  
2017 ◽  
Vol 50 (04) ◽  
pp. 778-784 ◽  
Author(s):  
Thomas Poisson ◽  
Maria Ivanova ◽  
Tatiana Besset ◽  
Xavier Pannecoucke
Keyword(s):  
Important Class ◽  
Mild Conditions ◽  
Palladium Catalyzed

We report the palladium-catalyzed introduction of the di­fluoromethylposphonate unit onto aryl and heteroaryl iodides under mild conditions. Using the CuCF2PO(OEt)2 species generated in situ, the method allows the functionalization of various otherwise reluctant substrates. In addition, this reaction permits the formation of CF2PO(OEt)2-containing heterocycles, an important class of compounds. This process broadens the current toolbox of methods available to construct CF2PO(OEt)2-containing molecules.

Palladium-Catalyzed Decarboxylation of Benzyl Fluorobenzoates

Synlett ◽  
2017 ◽  
Vol 28 (19) ◽  
pp. 2573-2576 ◽  
Author(s):  
Ryoichi Kuwano ◽  
Yusuke Makida ◽  
Yasutaka Matsumoto
Keyword(s):  
Benzoic Acid ◽  
Catalytic Reaction ◽  
Functional Group ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Benzoic Acids ◽  
Benzyl Alcohols ◽  
Cross Coupling Reaction ◽  
Palladium Catalyzed

The decarboxylation of benzyl fluorobenzoates has been developed by using the palladium catalyst prepared in situ from Pd(η3-allyl)Cp and bulky monophosphine ligand XPhos. The catalytic reaction afforded a range of fluorinated diarylmethanes in good yields with broad functional-group compatibility. The substrates were readily synthesized by condensation of the corresponding benzoic acid with benzyl alcohol. Therefore, the transformation is formally regarded as a cross-coupling reaction between fluorine-containing benzoic acids and benzyl alcohols.

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