Palladium-catalyzed paraformaldehyde insertion: a three-component synthesis of benzofurans

2016 ◽  
Vol 14 (10) ◽  
pp. 2819-2823 ◽  
Author(s):  
Xiufang Cheng ◽  
Yi Peng ◽  
Jun Wu ◽  
Guo-Jun Deng
Keyword(s):  
Palladium Catalysis ◽  
Phenacyl Bromides ◽  
Palladium Catalyzed

2-Aroylbenzofurans were prepared from 2-bromophenols, phenacyl bromides and paraformaldehyde under palladium catalysis conditions.

Temporary (PO) directing group enabled carbazole ortho arylation via palladium catalysis

2021 ◽  
Vol 57 (16) ◽  
pp. 2021-2024
Author(s):  
Zhi-Chao Qi ◽  
Qin-Xin Lou ◽  
Yuan Niu ◽  
Shang-Dong Yang
Keyword(s):  
Palladium Catalysis ◽  
Palladium Catalyzed ◽  
Directing Group

An efficient palladium-catalyzed, temporary P(O) directing group assisted C–H bond arylation of carbazoles was achieved, accompanied by the directing group being self-shed spontaneously.

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.

scholarly journals Asymmetric synthesis of chiral cycloalkenone derivatives via palladium catalysis

2014 ◽  
Vol 5 (4) ◽  
pp. 1354-1360 ◽  
Author(s):  
Barry M. Trost ◽  
James T. Masters ◽  
Jean-Philip Lumb ◽  
Dahlia Fateen
Keyword(s):  
Natural Products ◽  
Asymmetric Synthesis ◽  
Palladium Catalysis ◽  
Building Blocks ◽  
Efficient Synthesis ◽  
Palladium Catalyzed

Palladium-catalyzed oxidative desymmetrization enables the efficient synthesis of both enantioenriched cycloalkenone building blocks and diverse epoxyquinoid natural products.

Coordination Effect Enabled Palladium-Catalyzed Regioselective O-Alkylation of 2-Pyridones

2022 ◽  
Author(s):  
Zhiqiang Lu ◽  
yanzhi li ◽  
yi ru ◽  
shujian yang ◽  
chu hao ◽  
...  
Keyword(s):  
Pyridine Ring ◽  
Palladium Catalysis ◽  
Palladium Catalyzed ◽  
Coordination Effect ◽  
High Yields

A novel tactic for regioselective O-alkylation of 2-pyridones has been realized through palladium catalysis in moderate to high yields. The coordination effect between palladium and nitrogen on pyridine ring plays...

scholarly journals A tandem Mannich addition–palladium catalyzed ring-closing route toward 4-substituted-3(2H)-furanones

2014 ◽  
Vol 10 ◽  
pp. 1462-1470 ◽  
Author(s):  
Jubi John ◽  
Eliza Târcoveanu ◽  
Peter G Jones ◽  
Henning Hopf
Keyword(s):  
Palladium Catalysis ◽  
Aromatic Aldehydes ◽  
Prostaglandin Analogues ◽  
Diazo Esters ◽  
Palladium Catalyzed ◽  
Facile Route

A facile route towards highly functionalized 3(2H)-furanones via a sequential Mannich addition–palladium catalyzed ring closing has been elaborated. The reaction of 4-chloroacetoacetate esters with imines derived from aliphatic and aromatic aldehydes under palladium catalysis afforded 4-substituted furanones in good to excellent yields. 4-Hydrazino-3(2H)-furanones could also be synthesized from diazo esters in excellent yields by utilising the developed strategy. We could also efficiently transform the substituted furanones to aza-prostaglandin analogues.

Palladium-Catalyzed C–H Bond Monofluorination of 2-Arylbenzo[d]oxazinone Using Nitrate as Crucial Promoter

Synthesis ◽  
2019 ◽  
Vol 51 (07) ◽  
pp. 1578-1584 ◽  
Author(s):  
Xu-Qin Li ◽  
Huu-Manh Vu ◽  
Fei-Wu Chen
Keyword(s):  
Functional Groups ◽  
Palladium Catalysis ◽  
Environmentally Friendly ◽  
Palladium Catalyzed ◽  
Plausible Mechanism

Monofluorination of 2-arylbenzo[d]oxazinones with N-fluorobenzenesulfonimide (NFSI) was achieved by palladium catalysis in moderate to good yields. Promoted by nitrate, the reaction provides an economic and environmentally friendly strategy. The synthesis of monofluorinated 2-arylbenzo[d]oxazinones has good compatibility with many common functional groups. The plausible mechanism of this monofluorination is discussed.

scholarly journals Mechanistic investigations of bipyrimidine-promoted palladium-catalyzed allylic acetoxylation of olefins

2009 ◽  
Vol 87 (1) ◽  
pp. 264-271 ◽  
Author(s):  
Bo-Lin Lin ◽  
Jay A Labinger ◽  
John E Bercaw
Keyword(s):  
Acetic Acid ◽  
Key Words ◽  
Palladium Catalysis ◽  
Allylic Oxidation ◽  
Competition Experiment ◽  
Catalyst Precursor ◽  
Mechanistic Studies ◽  
Allyl Acetate ◽  
Palladium Catalyzed ◽  
Terminal Olefins

Several pyridine-like ligands were found to improve Pd(OAc)2-catalyzed allylic oxidation of allylbenzene to cinnamyl acetate by p-benzoquinone in acetic acid. The best ligand examined, bipyrimidine, was used to identify the catalyst precursor for this system, (bipyrimidine)Pd(OAc)2, which was fully characterized. Mechanistic studies suggest the reaction takes place through disproportionation of (bipyrimidine)Pd(OAc)2 to form a bipyrimidine-bridged dimer, which reacts with olefin to form a PdII-olefin adduct, followed by allylic C–H activation to produce (η3-allyl)PdII species. The (η3-allyl)PdII intermediate undergoes a reversible acetate attack to generate a Pd0-(allyl acetate) adduct, which subsequently reacts with p-benzoquinone to release allyl acetate and regenerate (bipyrimidine)Pd(OAc)2. No KIE is observed for the competition experiment between allylbenzene-d0 and allylbenzene-d5 (CD2=CDCD2C6H5), suggesting that allylic C–H activation is not rate-determining. Catalytic allylic acetoxylations of other terminal olefins as well as cyclohexene were also effected by (bipyrimidine)Pd(OAc)2.Key words: olefin, palladium catalysis, allylic C–H oxidation, p-benzoquinone, bipyrimidine.

scholarly journals Bipyridylacetylenes 1: the synthesis of some bipyridylacetylenes via the palladium-catalyzed coupling of acetylenes with 2,2′-dibromobipyridyl, and the single crystal X-ray structure of 6,6′-bisphenylethynyl-2,2′-bipyridine

1991 ◽  
Vol 69 (7) ◽  
pp. 1117-1123 ◽  
Author(s):  
Ian R. Butler ◽  
Chantal Soucy-Breau
Keyword(s):  
Crystal Structure ◽  
Single Crystal ◽  
Key Words ◽  
Dihedral Angle ◽  
Palladium Catalysis ◽  
Crystal Data ◽  
X Ray ◽  
Acetylenic Bond ◽  
Palladium Catalyzed

The synthesis of a series of 6,6′-diethynyl-2,2′-bipyridyls from the palladium-catalyzed coupling of 6,6′-dibromo-2,2′-bipyridine with a series of arylacetylenes is reported. The single crystal X-ray structure of 6,6′-phenylethynyl-2,2′-bipyridyl was determined. Crystal data: monoclinic, A2/a, with cell constants a = 10.0385(4), b = 9.2166(4), c = 21.4130(8) Å, and β = 102.981(3)°; Dcalc. = 1.226 g cm−3, Z = 4, Rf = 0.045, S = 1.22, using 886 reflections of the 1443 unique reflections. The packing diagram indicates essentially that the molecules pack in a layered assembly with the nitrogen atoms of the dipyridyl groups on opposite sides and with a dihedral angle of 59.85(16)° between the pyridyl and phenyl groups. The acetylenic bond distances are normal. Key words: acetylene, palladium, catalysis, coupling, monomers, crystal structure.

General and practical intramolecular decarbonylative coupling of thioesters via palladium catalysis

2021 ◽  
Author(s):  
Han Cao ◽  
Xuejing Liu ◽  
Fusheng Bie ◽  
Yijun Shi ◽  
Ying Han ◽  
...  
Keyword(s):  
Bond Cleavage ◽  
Palladium Catalysis ◽  
Palladium Catalyzed

We report a general and practical palladium-catalyzed intramolecular decarbonylative coupling of thioesters via C–S bond cleavage, decarbonylation and C–S bond reformation.

Palladium-catalyzed asymmetric allylic amination of a vinylethylene carbonate with N-heteroaromatics

2021 ◽  
Author(s):  
Chao Xia ◽  
Dong-Chao Wang ◽  
Gui-Rong Qu ◽  
Hai-Ming Guo
Keyword(s):  
Palladium Catalysis ◽  
Allylic Amination ◽  
Acyclic Nucleosides ◽  
Palladium Catalyzed

Highly enantioselective allylic amination of a vinylethylene carbonate with N-heteroaromatics is enabled by asymmetric palladium catalysis for the synthesis of chiral acyclic nucleosides and isonucleosides.

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