Palladium-catalyzed Heck-type reaction of oximes with allylic alcohols: synthesis of pyridines and azafluorenones

2016 ◽  
Vol 52 (1) ◽  
pp. 84-87 ◽  
Author(s):  
Meifang Zheng ◽  
Pengquan Chen ◽  
Wanqing Wu ◽  
Huanfeng Jiang
Keyword(s):  
Allylic Alcohol ◽  
Allylic Alcohols ◽  
Type Reaction ◽  
Palladium Catalyzed

An efficient palladium-catalyzed Heck-type reaction of oximes with allylic alcohol has been developed for the synthesis of pyridines and azafluorenones.

scholarly journals Pd-Catalyzed Cyclocarbonylation of Allylic Alcohol under Benign Conditions with Ionic Liquid as Stabilizer

Materials ◽  
2020 ◽  
Vol 13 (9) ◽  
pp. 2093
Author(s):  
Nasrin Nemati ◽  
Reza Eslamloueyan ◽  
Amalie Modvig ◽  
Anders Riisager
Keyword(s):  
Ionic Liquid ◽  
Catalyst System ◽  
Allylic Alcohol ◽  
Allylic Alcohols ◽  
Optimal Conditions ◽  
Consecutive Reactions ◽  
Partial Pressures ◽  
Palladium Catalyzed ◽  
First Time ◽  
Time Of Reaction

Homogeneous palladium-catalyzed (Pd-catalyzed) cyclocarbonylation of unsaturated allylic alcohols and alkynols in the presence of hydrogen forms lactone products with important applications in the food, perfume, and polymer industry. In this work, the cyclocarbonylation of 2-methyl-3-buten-2-ol was studied for the first time using a very active Pd-DPEphos (bis[(2-diphenylphosphino)phenyl]ether) catalyst in the presence of the ionic liquid (IL) [BMIM]Cl (1-butyl-3-methylimidazolium chloride) in dichloromethane to selectively produce 4,4-dimethyl-γ-butyrolactone. The effect of different parameters such as temperature, gas partial pressures, time of reaction, substrate and ligand concentrations were investigated and found to provide optimal conditions for lactonization (95 °C, 28 bar (CO/H2/N2: 20/5/3)), 18 h, 0.1 M substrate, and 16 mol% DPEphos), which were significantly milder than previously reported systems for cyclocarbonylation. Importantly, the study further showed that presence of the IL in the reaction mixture provided stabilization of the catalyst system and prevented formation of Pd-black, which allowed reuse of the catalytic system in consecutive reactions after intermediate extraction of the lactone product.

Carbon dioxide-promoted palladium-catalyzed dehydration of primary allylic alcohol: access to substituted 1,3-dienes

2020 ◽  
Author(s):  
Yan-Kai Huang ◽  
Wen-Zhen Zhang ◽  
Ke Zhang ◽  
Wen-Le Wang ◽  
Xiaobing Lu
Keyword(s):  
Carbon Dioxide ◽  
Allylic Alcohol ◽  
Allylic Alcohols ◽  
Dehydration Reaction ◽  
Alcohol Access ◽  
Palladium Catalyzed

1,3-dienes are versatile synthons and important monomers. Herein we report a carbon dioxide promoted dehydration reaction of primary allylic alcohols to produce substituted 1,3-dienes in good yields. Taking advantage of...

Direct and Selective Synthesis of Adipic and Other Dicarboxylic Acids by Palladium‐Catalyzed Carbonylation of Allylic Alcohols

2020 ◽  
Vol 59 (46) ◽  
pp. 20394-20398
Author(s):  
Ji Yang ◽  
Jiawang Liu ◽  
Yao Ge ◽  
Weiheng Huang ◽  
Helfried Neumann ◽  
...  
Keyword(s):  
Dicarboxylic Acids ◽  
Allylic Alcohols ◽  
Selective Synthesis ◽  
Palladium Catalyzed

Recent Developments in Heck-Type Reaction of Unactivated Alkenes and Alkyl Electrophiles

Synthesis ◽  
2020 ◽  
Author(s):  
Lili Shi ◽  
Junkai Fu ◽  
Shuangqiu Gao ◽  
Le Chang ◽  
Binglin Wang
Keyword(s):  
Heck Reaction ◽  
Alkyl Radicals ◽  
Type Reaction ◽  
The Past ◽  
Alkyl Electrophiles ◽  
Recent Developments ◽  
Palladium Catalyzed ◽  
Initial Work ◽  
Activated Olefins ◽  
Pseudo Halides

AbstractThe Mizoroki–Heck reaction is considered as one of the most ingenious and widely used methods for constructing C–C bonds. This reaction mainly focuses on activated olefins (styrenes, acrylates, or vinyl ethers) and aryl/vinyl (pseudo) halides. In comparison, the studies on unactivated alkenes and alkyl electrophiles are far less due to the low reactivity, poor selectivity, as well as competitive β-H elimination. In the past years, a growing interest has thus been devoted and significant breakthroughs have been achieved in the employment of unactivated alkenes and alkyl electrophiles as the reaction components, and this type of coupling is called as Heck-type or Heck-like reaction, which distinguishes from the traditional Heck reaction. Herein, we give a brief summary on Heck-type reaction between unactivated alkenes and alkyl electrophlies, covering its initial work, recent advancements, and mechanistic discussions.1 Introduction2 Intramolecular Heck-Type Reaction of Unactivated Alkenes and Alkyl Electrophiles2.1 Cobalt-Catalyzed Intramolecular Heck-Type Reaction2.2 Palladium-Catalyzed Intramolecular Heck-Type Reaction2.3 Nickel-Catalyzed Intramolecular Heck-Type Reaction2.4 Photocatalysis and Multimetallic Protocol for Intramolecular Heck-Type Reaction3 Intermolecular Heck-Type Reaction of Unactivated Alkenes and Alkyl Electrophiles3.1 Electrophilic Trifluoromethylating Reagent as Reaction Partners3.2 Alkyl Electrophiles as Reaction Partners4 Oxidative Heck-Type Reaction of Unactivated Alkenes and Alkyl Radicals5 Conclusions and Outlook

scholarly journals Palladium-catalyzed Tsuji–Trost-type reaction of benzofuran-2-ylmethyl acetates with nucleophiles

RSC Advances ◽  
2021 ◽  
Vol 11 (2) ◽  
pp. 909-917
Author(s):  
Antonio Arcadi ◽  
Giancarlo Fabrizi ◽  
Andrea Fochetti ◽  
Francesca Ghirga ◽  
Antonella Goggiamani ◽  
...  
Keyword(s):  
Nucleophilic Substitution ◽  
Type Reaction ◽  
Palladium Catalyzed

The palladium-catalyzed benzylic-like nucleophilic substitution of benzofuran-2-ylmethyl acetate with N, S, O and C soft nucleophiles.

Cyanoalkylation/alkynylation of allylic alcohol through intramolecular radical 1,2-alkynyl migration

2021 ◽  
Vol 19 (11) ◽  
pp. 2416-2419
Author(s):  
Shengnan Jin ◽  
Fan Chen ◽  
Pengcheng Qian ◽  
Jiang Cheng
Keyword(s):  
Allylic Alcohol ◽  
Allylic Alcohols ◽  
Butyl Peroxide

A di-tert-butyl peroxide (DTBP)-promoted difunctionalization of α-aryl α-alkynyl allylic alcohols with alkyl nitriles was developed, affording a series of α-alkynyl γ-cyano functionalized ketones in moderate yields.

Formation of α,β-unsaturated carbonyl compounds by palladium-catalyzed oxidation of allylic alcohols

1994 ◽  
Vol 35 (38) ◽  
pp. 7097-7098 ◽  
Author(s):  
Enrique Gómez-Bengoa ◽  
Pedro Noheda ◽  
Antonio M. Echavarren
Keyword(s):  
Carbonyl Compounds ◽  
Allylic Alcohols ◽  
Palladium Catalyzed ◽  
Catalyzed Oxidation
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