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

Organic Chemistry Frontiers ◽

10.1039/d0qo01465f ◽

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...

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

Materials ◽

10.3390/ma13092093 ◽

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.

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

Chemical Communications ◽

10.1039/c5cc06958k ◽

2016 ◽

Vol 52 (1) ◽

pp. 84-87 ◽

Cited By ~ 49

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.

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

Angewandte Chemie International Edition ◽

10.1002/anie.202008916 ◽

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

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Allylic alcohols as synthons of allylic carbanions. Palladium-catalyzed carbonyl allylation by allylic alcohols with tin dichloride

Journal of the American Chemical Society ◽

10.1021/ja00221a091 ◽

1988 ◽

Vol 110 (13) ◽

pp. 4473-4474 ◽

Cited By ~ 83

Author(s):

Yoshiro. Masuyama ◽

Jun P. Takahara ◽

Yasuhiko. Kurusu

Keyword(s):

Allylic Alcohols ◽

Palladium Catalyzed ◽

Carbonyl Allylation

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

Organic & Biomolecular Chemistry ◽

10.1039/d1ob00192b ◽

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.

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