Palladium-Catalyzed Enantioselective C(sp3)–H/C(sp3)–H Umpolung Coupling of N-Allylimine and α-Aryl Ketones

2021 ◽  
Author(s):  
Tian-Ci Wang ◽  
Ling Zhu ◽  
Shiwei Luo ◽  
Zhong-Sheng Nong ◽  
Pu-Sheng Wang ◽  
...  
Keyword(s):  
Aryl Ketones ◽  
Palladium Catalyzed

scholarly journals Palladium-catalyzed alkylation of unactivated olefins

2004 ◽  
Vol 76 (3) ◽  
pp. 671-678 ◽  
Author(s):  
Ross A. Widenhoefer
Keyword(s):  
Good Yield ◽  
Catalytic Amount ◽  
Outer Sphere ◽  
Deuterium Labeling ◽  
Carbon Nucleophiles ◽  
Keto Esters ◽  
Reactive Carbon ◽  
Aryl Ketones ◽  
Palladium Catalyzed ◽  
Hydride Elimination

The reaction of a 3-butenyl β-diketone with a catalytic amount of PdCl2(CH3CN)2 in dioxane at room temperature led to olefin hydroalkylation and formation of the corresponding 2-acylcyclohexanone in good yield as a single regioisomer. Deuterium-labeling experiments for the hydroalkylation of 7-octene-2,4-dione were in accord with a mechanism involving outer-sphere attack of the pendant enol on a palladium-complexed olefin to form a palladium cyclohexyl species, followed by palladium migration via iterative β-hydride elimination/addition and protonolysis from a palladium enolate complex. In comparison to a 3-butenyl β-diketone, reaction of a 4-pentenyl β-diketone with a catalytic amount of PdCl2(CH3CN)2 in the presence of CuCl2 led to oxidative alkylation and formation of the corresponding 2-acyl-3-methyl-2-cyclohexenone in good yield as a single isomer. Unactivated olefins tethered to less reactive carbon nucleophiles such as β-keto esters, α-aryl ketones, and even dialkyl ketones underwent palladium-catalyzed hydroalkylation in the presence of Me3SiCl or HCl to form the corresponding cyclohexanones in moderate-to-good yield with high regioselectivity.

Efficient synthesis of alkyl aryl ketones & ketals via palladium-catalyzed regioselective arylation of vinyl ethers

2010 ◽  
Vol 8 (9) ◽  
pp. 2012 ◽  
Author(s):  
Mingcui Liu ◽  
Zeynab Hyder ◽  
Yawei Sun ◽  
Weijun Tang ◽  
Lijin Xu ◽  
...  
Keyword(s):  
Efficient Synthesis ◽  
Vinyl Ethers ◽  
Alkyl Aryl ◽  
Aryl Ketones ◽  
Palladium Catalyzed

Palladium catalyzed decarboxylative acylation of arylboronic acid with ethyl cyanoacetate as a new acylating agent: synthesis of alkyl aryl ketones

2015 ◽  
Vol 39 (11) ◽  
pp. 8763-8770 ◽  
Author(s):  
Md Yousuf ◽  
Tuluma Das ◽  
Susanta Adhikari
Keyword(s):  
Ethyl Cyanoacetate ◽  
Acylating Agent ◽  
Arylboronic Acid ◽  
One Pot ◽  
Alkyl Aryl ◽  
One Pot Synthesis ◽  
Aryl Ketones ◽  
Palladium Catalyzed

The versatile, one-pot synthesis of a series of alkyl aryl ketones is described using ethyl cyanoacetate as a new acylating agent.

ChemInform Abstract: Palladium-Catalyzed Synthesis of Aryl Ketones from Carboxylic Acids and Arylboronic Acids Using EEDQ.

ChemInform ◽  
2011 ◽  
Vol 42 (6) ◽  
pp. no-no
Author(s):  
Young Bum Kwon ◽  
Bo Ram Choi ◽  
Seung Hwan Lee ◽  
Jin-soo Seo ◽  
Cheol Min Yoon
Keyword(s):  
Carboxylic Acids ◽  
Arylboronic Acids ◽  
Aryl Ketones ◽  
Palladium Catalyzed

ChemInform Abstract: Palladium-Catalyzed Carbonylation of Indoles Using Aryl Formates as Bifunctional Reagents: A Route to Indol-3-yl Aryl Ketones.

ChemInform ◽  
2016 ◽  
Vol 47 (47) ◽  
Author(s):  
Li-Jun Gu ◽  
Yu-Shen Wang ◽  
Hong-Tao Zhang ◽  
Huai-Jun Tang ◽  
Gan-Peng Li ◽  
...  
Keyword(s):  
Aryl Ketones ◽  
Palladium Catalyzed
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