Chemoselective and Metal-Free Synthesis of Aryl Esters from the Corresponding Benzylic Alcohols in Aqueous Medium Using TBHP/TBAI as an Efficient Catalytic System

Synlett ◽  
2018 ◽  
Vol 29 (16) ◽  
pp. 2208-2212
Author(s):  
Sanjay Bhar ◽  
Sneha Nandy ◽  
Avishek Ghatak ◽  
Asit Das
Keyword(s):  
Transition Metal ◽  
Catalytic Amount ◽  
High Yield ◽  
Primary Alcohols ◽  
Benzylic Alcohols ◽  
Metal Free ◽  
Tishchenko Reaction ◽  
Tert Butyl Hydroperoxide ◽  
Wide Range ◽  
Tetrabutylammonium Iodide

A novel and transition-metal-free strategy has been developed for the synthesis of aryl esters starting from corresponding benzylic primary alcohols as the exclusive substrates using tert-butyl hydroperoxide (TBHP) as a terminal oxidant in the presence of catalytic amount of tetrabutylammonium iodide (TBAI) and imidazole, where the aliphatic alcohols remained unaffected. These reactions are highly chemoselective and associated with high yield and wide applicability accommodating a wide range of substituents. Excellent chemoselectivity has also been demonstrated through intramolecular competition experiments. This protocol can be considered as an important analogue of Tishchenko reaction using benzylic alcohols as the substrates instead of benzaldehydes.

TBHP/n-Bu4PBr-Promoted Oxidative Cross-Dehydrogenative Coupling of Aryl Methanols: A Facile Synthesis of Symmetrical Carboxylic Anhydride Derivatives

Synlett ◽  
2017 ◽  
Vol 29 (01) ◽  
pp. 136-140
Author(s):  
Mehdi Adib ◽  
Rahim Pashazadeh
Keyword(s):  
Transition Metal ◽  
Coupling Reaction ◽  
Catalytic Amount ◽  
Facile Synthesis ◽  
Butyl Hydroperoxide ◽  
Metal Free ◽  
Tert Butyl ◽  
Dehydrogenative Coupling ◽  
Tert Butyl Hydroperoxide ◽  
Methylene Groups

A transition-metal-free oxidative cross-dehydrogenative coupling reaction has been developed for the preparation of symmetrical carboxylic anhydrides through self-coupling dual C–O bond formations of aryl methanols. In the presence of a catalytic amount of tetrabutylphosphonium bromide (TBPB) as transfer agent and aqueous tert-butyl hydroperoxide (TBHP) as oxidant and reactant, methylene groups of aryl methanols were efficiently oxidized to C=O and coupled with the peroxide oxygen from TBHP to form a diverse array of symmetrical carboxylic anhydride derivatives.

scholarly journals MXenes for future nanophotonic device applications

Nanophotonics ◽  
2020 ◽  
Vol 9 (7) ◽  
pp. 1831-1853
Author(s):  
Jaeho Jeon ◽  
Yajie Yang ◽  
Haeju Choi ◽  
Jin-Hong Park ◽  
Byoung Hun Lee ◽  
...  
Keyword(s):  
Solar Cells ◽  
Transition Metal ◽  
Wide Spectrum ◽  
Building Blocks ◽  
Optoelectronic Device ◽  
High Yield ◽  
Saturable Absorption ◽  
Nanophotonic Device ◽  
Wide Range ◽  
Device Applications

AbstractTwo-dimensional (2D) layers of transition metal carbides, nitrides, or carbonitrides, collectively referred to as MXenes, are considered as the new family of 2D materials for the development of functional building blocks for optoelectronic and photonic device applications. Their advantages are based on their unique and tunable electronic and optical properties, which depend on the modulation of transition metal elements or surface functional groups. In this paper, we have presented a comprehensive review of MXenes to suggest an insightful perspective on future nanophotonic and optoelectronic device applications based on advanced synthesis processes and theoretically predicted or experimentally verified material properties. Recently developed optoelectronic and photonic devices, such as photodetectors, solar cells, fiber lasers, and light-emitting diodes are summarized in this review. Wide-spectrum photodetection with high photoresponsivity, high-yield solar cells, and effective saturable absorption were achieved by exploiting different MXenes. Further, the great potential of MXenes as an electrode material is predicted with a controllable work function in a wide range (1.6–8 eV) and high conductivity (~104 S/cm), and their potential as active channel material by generating a tunable energy bandgap is likewise shown. MXene can provide new functional building blocks for future generation nanophotonic device applications.

Regioselective 1,4-conjugate aza-Michael addition of dienones with benzotriazole

2017 ◽  
Vol 23 (4) ◽  
Author(s):  
Zheng Li ◽  
Tianpeng Li ◽  
Rugang Fu ◽  
Jingya Yang
Keyword(s):  
Transition Metal ◽  
Michael Addition ◽  
Potassium Acetate ◽  
High Yield ◽  
Metal Free ◽  
Mild Conditions

AbstractThe regioselective 1,4-conjugate aza-Michael addition of dienones with benzotriazole catalyzed by potassium acetate is described. A series of 3-(benzotriazol-1-yl)-1,5-diarylpent-4-en-1-ones were efficiently synthesized under mild conditions. This protocol has advantages of transition-metal free catalyst, high yield and high regioselectivity.

Deuterated Aryl Alkyl Ethers Synthesis via Nucleophilic Etherification of Aryl Alkyl Ethers and Thioethers with Deuterated Alcohols

Synlett ◽  
2019 ◽  
Vol 30 (15) ◽  
pp. 1805-1809
Author(s):  
Shuai Li ◽  
Xia Wang ◽  
Xin-Ge Yang ◽  
Gui-Quan Yu ◽  
Xue-Qiang Wang
Keyword(s):  
Transition Metal ◽  
Nucleophilic Aromatic Substitution ◽  
Aromatic Substitution ◽  
Mechanistic Studies ◽  
Reaction Conditions ◽  
Metal Free ◽  
Wide Range ◽  
Alkyl Ethers

A transition-metal-free etherification protocol that is capable of synthesizing deuterated ethers is described. A wide range of aryl alkyl ethers and thioethers were suitable for this transformation owing to the mild reaction conditions. Besides, a series of sterically bulky deuterated alcohols were successfully incorporated into cyano-substituted arenes. The results of mechanistic studies suggested this reaction might take place via nucleophilic aromatic substitution pathway.

Lithium tert-butoxide mediated α-alkylation of ketones with primary alcohols under transition-metal-free conditions

RSC Advances ◽  
2013 ◽  
Vol 3 (21) ◽  
pp. 7739 ◽  
Author(s):  
Yu-Feng Liang ◽  
Xin-Feng Zhou ◽  
Shi-Ya Tang ◽  
Yao-Bing Huang ◽  
Yi-Si Feng ◽  
...  
Keyword(s):  
Transition Metal ◽  
Primary Alcohols ◽  
Metal Free

The phosphinoboration of carbodiimides, isocyanates, isothiocyanates and CO2

2017 ◽  
Vol 46 (33) ◽  
pp. 10876-10885 ◽  
Author(s):  
Stephen J. Geier ◽  
James H. W. LaFortune ◽  
Diya Zhu ◽  
Stephanie C. Kosnik ◽  
Charles L. B. Macdonald ◽  
...  
Keyword(s):  
Carbon Dioxide ◽  
Transition Metal ◽  
High Yield ◽  
Metal Free

The transition metal-free addition of phosphinoboronate ester Ph2PBpin (pin = 1,2-O2C2Me4) to heterocumulenes including carbodiimides, isocyanates, isothiocyanates and carbon dioxide proceeds with remarkable selectivity to give products in high yield.

Transition-metal-free aerobic oxidation of primary alcohols to carboxylic acids

2013 ◽  
Vol 37 (6) ◽  
pp. 1700 ◽  
Author(s):  
Jing Wang ◽  
Chao Liu ◽  
Jiwen Yuan ◽  
Aiwen Lei
Keyword(s):  
Transition Metal ◽  
Carboxylic Acids ◽  
Aerobic Oxidation ◽  
Primary Alcohols ◽  
Metal Free

A remarkable effect of ionic liquids in transition-metal-free aerobic oxidation of benzylic alcohols

2011 ◽  
Vol 52 (41) ◽  
pp. 5392-5394 ◽  
Author(s):  
Yoshiro Oda ◽  
Koji Hirano ◽  
Tetsuya Satoh ◽  
Susumu Kuwabata ◽  
Masahiro Miura
Keyword(s):  
Ionic Liquids ◽  
Transition Metal ◽  
Aerobic Oxidation ◽  
Remarkable Effect ◽  
Benzylic Alcohols ◽  
Metal Free
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