Palladium-Catalyzed Carbonylative Synthesis of Aryl Esters from p-Benzoquinones and Aryl Triflates

2021 ◽  
Author(s):  
Xiao-Feng Wu ◽  
jun ying ◽  
Jian-Shu Wang ◽  
Zhengjie Le ◽  
Siqi Wang
Keyword(s):  
Reaction Proceeds ◽  
Palladium Catalyzed

A palladium-catalyzed dicarbonylation of p-benzoquinones with aryl triflates has been developed. Using Cr(CO)6 as the CO source, the reaction proceeds smoothly and efficiently to give a series of aryl esters...

Intermolecular C–H Amidation of Alkenes with Carbon Monoxide and Azides via Tandem Palladium Catalysis

Synthesis ◽  
2021 ◽  
Author(s):  
Zheng-Yang Gu ◽  
Yang Wu ◽  
Feng Jin ◽  
Bao Xiaoguang ◽  
Ji-Bao Xia
Keyword(s):  
Carbon Monoxide ◽  
Palladium Catalysis ◽  
Computational Studies ◽  
Organic Azides ◽  
Reaction Proceeds ◽  
Palladium Catalyzed ◽  
Directing Group ◽  
And Control

An atom- and step-economic intermolecular multi-component palladium-catalyzed C–H amidation of alkenes with carbon monoxide and organic azides has been developed for the synthesis of alkenyl amides. The reaction proceeds efficiently without an ortho-directing group on the alkene substrates. Nontoxic dinitrogen is generated as the sole by-product. Computational studies and control experiments have revealed that the reaction takes place via an unexpected mechanism by tandem palladium catalysis.

Synthesis of 4-Alkylidene-Substituted 1,2,3,4-Tetrahydroisoquinolines via Palladium-Catalyzed Carbopalladation/C–H Activation of 2-Bromobenzyl-N-propargylamines

Synthesis ◽  
2015 ◽  
Vol 47 (11) ◽  
pp. 1633-1642 ◽  
Author(s):  
Kanagaraj Naveen ◽  
Avanashiappan Nandakumar ◽  
Paramasivan Perumal
Keyword(s):  
Bond Activation ◽  
Domino Reaction ◽  
Coupling Reactions ◽  
Reaction Proceeds ◽  
Palladium Catalyzed ◽  
A3 Coupling

Tetrasubstituted alkene-based 1,2,3,4-tetrahydroisoquinolines are synthesized via the formation of a cyclic carbopalladation complex followed by C–H bond activation of the sp2 carbon in arenes. This domino reaction proceeds with good selectivity and provides good yields of the products. The requisite starting materials are synthesized by copper(I) iodide catalyzed A3-coupling reactions.

scholarly journals Palladium-catalyzed substitution of (coumarinyl)methyl acetates with C-, N-, and S-nucleophiles

2012 ◽  
Vol 8 ◽  
pp. 1200-1207 ◽  
Author(s):  
Kalicharan Chattopadhyay ◽  
Erik Fenster ◽  
Alexander J Grenning ◽  
Jon A Tunge
Keyword(s):  
Nucleophilic Substitution ◽  
Biologically Active ◽  
New Method ◽  
Biological Screening ◽  
Different Types ◽  
Reaction Proceeds ◽  
Palladium Catalyzed

The palladium-catalyzed nucleophilic substitution of (coumarinyl)methyl acetates is described. The reaction proceeds though a palladium π-benzyl-like complex and allows for many different types of C-, N-, and S-nucleophiles to be regioselectively added to the biologically active coumarin motif. This new method was utilized to prepare a 128-membered library of aminated coumarins for biological screening.

scholarly journals Palladium-catalyzed Heck-type reaction of secondary trifluoromethylated alkyl bromides

2017 ◽  
Vol 13 ◽  
pp. 2610-2616 ◽  
Author(s):  
Tao Fan ◽  
Wei-Dong Meng ◽  
Xingang Zhang
Keyword(s):  
Alkyl Radical ◽  
Functional Group ◽  
High Efficiency ◽  
Mechanistic Studies ◽  
Reaction Conditions ◽  
Type Reaction ◽  
Alkyl Bromides ◽  
Reaction Proceeds ◽  
Palladium Catalyzed ◽  
Hydroxy Groups

An efficient palladium-catalyzed Heck-type reaction of secondary trifluoromethylated alkyl bromides has been developed. The reaction proceeds under mild reaction conditions with high efficiency and excellent functional group tolerance, even towards formyl and hydroxy groups. Preliminary mechanistic studies reveal that a secondary trifluoromethylated alkyl radical is involved in the reaction.

Ligand-Free Palladium-Catalyzed Carbonylative Suzuki Couplings of Vinyl Iodides with Arylboronic Acids under Substoichiometric Base Conditions

Synlett ◽  
2021 ◽  
Author(s):  
Zhiyuan Yang ◽  
Pei-Xue Gong ◽  
Junjie Chen ◽  
Jie Zhang ◽  
Xu Gong ◽  
...  
Keyword(s):  
Late Stage ◽  
Ambient Pressure ◽  
Complex Molecule ◽  
Arylboronic Acids ◽  
Simple Protocol ◽  
Ligand Free ◽  
Reaction Proceeds ◽  
Palladium Catalyzed ◽  
Vinyl Iodides

A ligand-free palladium-catalyzed carbonylation of vinyl iodides with arylboronic acids allowing for the synthesis of chalcones and α-branched enones has been established. This reaction proceeds smoothly under ambient pressure and temperature and even use of substoichiometric base renders the transformation to work well. Importantly, this mild, efficient, operationally simple protocol is suitable for the late-stage functionalization of an epiandrosterone-derived complex molecule.

scholarly journals Palladium-catalyzed picolinamide-directed iodination of remote ortho-C−H bonds of arenes: Synthesis of tetrahydroquinolines

2016 ◽  
Vol 12 ◽  
pp. 1243-1249 ◽  
Author(s):  
William A Nack ◽  
Xinmou Wang ◽  
Bo Wang ◽  
Gang He ◽  
Gong Chen
Keyword(s):  
Electrophilic Aromatic Substitution ◽  
Aromatic Substitution ◽  
Iodination Reaction ◽  
Reaction Proceeds ◽  
Palladium Catalyzed

A new palladium-catalyzed picolinamide (PA)-directed ortho-iodination reaction of ε-C(sp2)−H bonds of γ-arylpropylamine substrates is reported. This reaction proceeds selectively with a variety of γ-arylpropylamines bearing strongly electron-donating or withdrawing substituents, complementing our previously reported PA-directed electrophilic aromatic substitution approach to this transformation. As demonstrated herein, a three step sequence of Pd-catalyzed γ-C(sp3)−H arylation, Pd-catalyzed ε-C(sp2)−H iodination, and Cu-catalyzed C−N cyclization enables a streamlined synthesis of tetrahydroquinolines bearing diverse substitution patterns.

Metal-assisted amination with oxime derivatives

2002 ◽  
Vol 74 (1) ◽  
pp. 143-149 ◽  
Author(s):  
Koichi Narasaka
Keyword(s):  
Oxidative Addition ◽  
Catalytic Amount ◽  
Grignard Reagents ◽  
Electrophilic Amination ◽  
Initial Formation ◽  
Alkyl Amines ◽  
Reaction Proceeds ◽  
Palladium Catalyzed ◽  
Oxime Derivatives ◽  
Hydrolysis Of

Electrophilic amination of Grignard reagents is accomplished by using O-sulfonyl-oximes of benzophenone derivatives. In the presence of a catalytic amount of CuCN, O-sulfonyloxime of 4,4¢-bis(trifluoromethyl)benzophenone reacts with alkyl Grignard reagents in tetrahydrofuran (THF) and hexamethylphosphoramide (HMPA), yielding primary alkyl-amines by successive hydrolysis of the resulting N-alkylimines. Arylamines are also prepared as well as alkylamines by treating O-sulfonyloxime of 3,3¢,5,5¢-tetrakis(trifluoromethyl)benzophenone in toluene-ether with Grignard reagents. Various cyclic imines are synthesized by palladium-catalyzed cyclization of olefinic oxime derivatives. That is, the reaction of O-pentafluorobenzoyloximes of olefinic ketones with a catalytic amount of Pd(PPh3)4 and triethylamine in dimethylformamide (DMF) affords nitrogen-containing heterocycles, such as pyrroles, pyridines, isoquinolines, spiro-imines, and aza-azulenes. This reaction proceeds via the initial formation of alkylideneaminopalladium species generated by oxidative addition of oximes to Pd(0), and the successive intramolecular Heck-type amination occurs on the olefinic moiety.

scholarly journals Continuous flow synthesis of indoles by Pd-catalyzed deoxygenation of 2-nitrostilbenes with carbon monoxide

RSC Advances ◽  
2017 ◽  
Vol 7 (17) ◽  
pp. 10469-10478 ◽  
Author(s):  
Gabriel Glotz ◽  
Bernhard Gutmann ◽  
Paul Hanselmann ◽  
Anna Kulesza ◽  
Dominique Roberge ◽  
...  
Keyword(s):  
Carbon Dioxide ◽  
Carbon Monoxide ◽  
Continuous Flow ◽  
Side Product ◽  
Flow Synthesis ◽  
Reaction Proceeds ◽  
Palladium Catalyzed

The palladium-catalyzed cyclization of o-vinylnitrobenzenes employing carbon monoxide as terminal reductant is investigated. The reaction proceeds with 1 to 2 mol% of Pd(OAc)2 and generates carbon dioxide as the only stoichiometric side-product.

scholarly journals Pd-Catalyzed Suzuki-Miyaura Cross-Coupling of Pentafluorophenyl Esters

Molecules ◽  
2018 ◽  
Vol 23 (12) ◽  
pp. 3134 ◽  
Author(s):  
Jonathan Buchspies ◽  
Daniel J. Pyle ◽  
Huixin He ◽  
Michal Szostak
Keyword(s):  
Cross Coupling ◽  
Mechanistic Studies ◽  
Reaction Proceeds ◽  
Pentafluorophenyl Esters ◽  
Palladium Catalyzed ◽  
Phenolic Esters ◽  
The Cross ◽  
Catalyst Systems ◽  
Significant Attention ◽  
General Method

Although the palladium-catalyzed Suzuki-Miyaura cross-coupling of aryl esters has received significant attention, there is a lack of methods that utilize cheap and readily accessible Pd-phosphane catalysts, and can be routinely carried out with high cross-coupling selectivity. Herein, we report the first general method for the cross-coupling of pentafluorophenyl esters (pentafluorophenyl = pfp) by selective C–O acyl cleavage. The reaction proceeds efficiently using Pd(0)/phosphane catalyst systems. The unique characteristics of pentafluorophenyl esters are reflected in the fully selective cross-coupling vs. phenolic esters. Of broad synthetic interest, this report establishes pentafluorophenyl esters as new, highly reactive, bench-stable, economical, ester-based, electrophilic acylative reagents via acyl-metal intermediates. Mechanistic studies strongly support a unified reactivity scale of acyl electrophiles by C(O)–X (X = N, O) activation. The reactivity of pfp esters can be correlated with barriers to isomerization around the C(acyl)–O bond.

STUDIES IN THE PYRROLINE SERIES: III. SOME PYRROLINYLPYRROLES AND RELATED COMPOUNDS

1964 ◽  
Vol 42 (5) ◽  
pp. 1073-1078 ◽  
Author(s):  
R. Bonnett ◽  
K. S. Chan ◽  
I. A. D. Gale
Keyword(s):  
Similar Sequence ◽  
Reaction Proceeds ◽  
Palladium Catalyzed ◽  
Related Compounds

The addition of 5,5-dimethyl-1-pyrroline to pyrrole gives both the 1:1 adduct and the 2:1 adduct. The palladium-catalyzed dehydrogenation of 2,2′-pyrrolidinylpyrrole has been studied at various temperatures. In refluxing toluene the reaction proceeds satisfactorily to the pyrroline level, while in cymene the corresponding bipyrrole is produced. 1,2′-(1′-Pyrrolinyl)-pyrrole has been obtained from the reaction of 2-methoxy-1-pyrroline with pyrrole: on pyrolysis it yields 2,2′-(1′-pyrrolinyl)pyrrole. A similar sequence is observed with 3,4-dimethylpyrrole.

Sign in / Sign up

Export Citation Format

Share Document