scholarly journals Palladium-catalyzed ligand-promoted site-selective cyanomethylation of unactivated C(sp3)–H bonds with acetonitrile

2016 ◽  
Vol 7 (4) ◽  
pp. 2804-2808 ◽  
Author(s):  
Yongbing Liu ◽  
Ke Yang ◽  
Haibo Ge
Keyword(s):  
Palladium Catalysis ◽  
Direct Coupling ◽  
Palladium Catalyzed ◽  
Site Selective

The direct coupling of unactivated sp3 C–H bonds in aliphatic amides with acetonitrile was achieved via palladium catalysis.

Theoretical and experimental studies of palladium-catalyzed site-selective C(sp3)−H bond functionalization enabled by transient ligands

2017 ◽  
Author(s):  
Haibo Ge ◽  
Lei Pan ◽  
Piaoping Tang ◽  
Ke Yang ◽  
Mian Wang ◽  
...  
Keyword(s):  
Bond Activation ◽  
Theoretical Calculations ◽  
Experimental Studies ◽  
Bond Functionalization ◽  
Aliphatic Ketones ◽  
Site Selectivity ◽  
Mechanistic Investigation ◽  
Palladium Catalyzed ◽  
Metal Catalyzed ◽  
Site Selective

Transition metal-catalyzed selective C–H bond functionalization enabled by transient ligands has become an extremely attractive topic due to its economical and greener characteristics. However, catalytic pathways of this reaction process on unactivated sp<sup>3</sup> carbons of reactants have not been well studied yet. Herein, detailed mechanistic investigation on Pd-catalyzed C(sp<sup>3</sup>)–H bond activation with amino acids as transient ligands has been systematically conducted. The theoretical calculations showed that higher angle distortion of C(sp2)-H bond over C(sp3)-H bond and stronger nucleophilicity of benzylic anion over its aromatic counterpart, leading to higher reactivity of corresponding C(sp<sup>3</sup>)–H bonds; the angle strain of the directing rings of key intermediates determines the site-selectivity of aliphatic ketone substrates; replacement of glycine with β-alanine as the transient ligand can decrease the angle tension of the directing rings. Synthetic experiments have confirmed that β-alanine is indeed a more efficient transient ligand for arylation of β-secondary carbons of linear aliphatic ketones than its glycine counterpart.<br><br>

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.

Site-Selective Aerobic C–H Monoacylation of Carbazoles Using Palladium Catalysis

2020 ◽  
Author(s):  
Subhadip Maiti ◽  
Tirtha Mandal ◽  
Barada Prasanna Dash ◽  
Jyotirmayee Dash
Keyword(s):  
Palladium Catalysis ◽  
Site Selective

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.

ChemInform Abstract: Generation of Diverse 2-Pyrones via Palladium-Catalyzed Site-Selective Suzuki-Miyaura Couplings of 3-Bromo-4-tosyloxy-2-pyrone.

ChemInform ◽  
2012 ◽  
Vol 43 (8) ◽  
pp. no-no
Author(s):  
Xiaoli Lei ◽  
Liang Gao ◽  
Qiuping Ding ◽  
Yiyuan Peng ◽  
Jie Wu
Keyword(s):  
Palladium Catalyzed ◽  
Site Selective

Non-directed highly para-selective C-H functionalization of TIPS-protected phenols promoted by a proton shuttle

2021 ◽  
Author(s):  
Jingyao Geng ◽  
Zhang Fang ◽  
Guangliang Tu ◽  
Yingsheng Zhao
Keyword(s):  
Bioactive Molecules ◽  
Protecting Group ◽  
Mechanism Study ◽  
Phenol Derivatives ◽  
Site Selectivity ◽  
Palladium Catalyzed ◽  
Direct Functionalization ◽  
Poor Site ◽  
Site Selective ◽  
First Time

Abstract Palladium-catalyzed non-directed C-H functionalization provides an efficient approach for direct functionalization of arenes, but it usually suffers from poor site selectivity, limiting its wide application. Herein, it is reported for the first time that the proton shuttle of 3,5-dimethyladamantane-1-carboxylic acid (1-DMAdCO2H) can affect the site selectivity during the C-H activation step in palladium-catalyzed non-directed C-H functionalization, leading to highly para-selective C-H olefination of TIPS-protected phenols. This transformation displayed good generality in realizing various other para-selective C-H functionalization reactions such as hydroxylation, halogenation, and allylation reactions. A wide variety of phenol derivatives including bioactive molecules of triclosan, thymol, and propofol, were compatible substrates, leading to the corresponding para-selective products in moderate to good yields. A preliminary mechanism study revealed that the spatial repulsion factor between proton shuttle and bulky protecting group resulted in the selective C-H activation at the less sterically hindered para-position. This new model non-directed para-selective C-H functionalization can provide a straightforward route for remote site-selective C-H activations.

Palladium-Catalyzed Site-Selective C(sp3)–H Arylation of Phenylacetaldehydes

2019 ◽  
Vol 21 (17) ◽  
pp. 7084-7088 ◽  
Author(s):  
Bo-Bo Gou ◽  
Hang-Fan Liu ◽  
Jie Chen ◽  
Ling Zhou
Keyword(s):  
Palladium Catalyzed ◽  
Site Selective

Recent Development in N-Auxilixary-Assisted Intramolecular Amination for Amine Substrates

Synlett ◽  
2015 ◽  
Vol 26 (08) ◽  
pp. 997-1002 ◽  
Author(s):  
Yingsheng Zhao ◽  
Chao Wang ◽  
Jian Han
Keyword(s):  
Transition Metal ◽  
Heterocyclic Compounds ◽  
Bond Formation ◽  
Direct Coupling ◽  
Significant Progress ◽  
Palladium Catalyzed ◽  
Directing Group

Direct coupling of N–H with C–H has aroused great attention in the last decades; during which the directing-group-assisted intramolecular C–N bond formation via transition metal has been achieved significant progress. Herein, we highlight the recent development in the directing-group-assisted intramolecular amination for amine substrates to build the important N-containing heterocyclic compounds.1 Introduction2 Triflamide-Promoted Intramolecular Amination3 Picolinamide-Assisted Intramolecular Amination4 Palladium-Catalyzed Intramolecular Amination under Assistance of Oxalyl Amide5 Conclusion

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