scholarly journals Carbamate-directed benzylic lithiation for the diastereo- and enantioselective synthesis of diaryl ether atropisomers

2011 ◽  
Vol 7 ◽  
pp. 1327-1333 ◽  
Author(s):  
Abigail Page ◽  
Jonathan Clayden
Keyword(s):  
Diethyl Ether ◽  
Enantioselective Synthesis ◽  
Diaryl Ethers ◽  
Diaryl Ether ◽  
Enantioselective Deprotonation

Diaryl ethers carrying carbamoyloxymethyl groups may be desymmetrised enantio- and diastereoselectively by the use of the sec-BuLi–(−)-sparteine complex in diethyl ether. Enantioselective deprotonation of one of the two benzylic positions leads to atropisomeric products with ca. 80:20 e.r.; an electrophilic quench typically provides functionalised atropisomeric diastereoisomers in up to 97:3 d.r.

tert-Butoxide mediated cascade desulfonylation/arylation/hydrolysis of cyclic sulfonyimines using diaryliodonium salts: synthesis of diaryl ether derivatives bearing a 2-aldehyde group

RSC Advances ◽  
2016 ◽  
Vol 6 (92) ◽  
pp. 89234-89237 ◽  
Author(s):  
Xiaofei Qian ◽  
Jianwei Han ◽  
Limin Wang
Keyword(s):  
Aldehyde Group ◽  
Diaryl Ethers ◽  
Diaryliodonium Salts ◽  
Diaryl Ether ◽  
Hydrolysis Of

Cascades of cyclic sulfonyimines mediated by tBuOK with diaryliodonium salts has been developed, giving the diaryl ethers in good yields.

scholarly journals Visible-light photoredox-catalyzed C–O bond cleavage of diaryl ethers by acridinium photocatalysts at room temperature

2020 ◽  
Vol 11 (1) ◽  
Author(s):  
Fang-Fang Tan ◽  
Xiao-Ya He ◽  
Wan-Fa Tian ◽  
Yang Li
Keyword(s):  
Carboxylic Acid ◽  
Visible Light ◽  
Room Temperature ◽  
Acid Catalysis ◽  
Bond Cleavage ◽  
Diphenyl Ether ◽  
One Pot ◽  
Diaryl Ethers ◽  
Diaryl Ether ◽  
High Bond

AbstractCleavage of C–O bonds in lignin can afford the renewable aryl sources for fine chemicals. However, the high bond energies of these C–O bonds, especially the 4-O-5-type diaryl ether C–O bonds (~314 kJ/mol) make the cleavage very challenging. Here, we report visible-light photoredox-catalyzed C–O bond cleavage of diaryl ethers by an acidolysis with an aryl carboxylic acid and a following one-pot hydrolysis. Two molecules of phenols are obtained from one molecule of diaryl ether at room temperature. The aryl carboxylic acid used for the acidolysis can be recovered. The key to success of the acidolysis is merging visible-light photoredox catalysis using an acridinium photocatalyst and Lewis acid catalysis using Cu(TMHD)2. Preliminary mechanistic studies indicate that the catalytic cycle occurs via a rare selective electrophilic attack of the generated aryl carboxylic radical on the electron-rich aryl ring of the diphenyl ether. This transformation is applied to a gram-scale reaction and the model of 4-O-5 lignin linkages.

scholarly journals Screening of ligands for the Ullmann synthesis of electron-rich diaryl ethers

2012 ◽  
Vol 8 ◽  
pp. 1105-1111 ◽  
Author(s):  
Nicola Otto ◽  
Till Opatz
Keyword(s):  
Low Temperatures ◽  
Potassium Phosphate ◽  
Model System ◽  
Multidentate Ligands ◽  
Copper Iodide ◽  
Structural Class ◽  
Diaryl Ethers ◽  
Aryl Bromides ◽  
Diaryl Ether ◽  
Ether Synthesis

In the search for new ligands for the Ullmann diaryl ether synthesis, permitting the coupling of electron-rich aryl bromides at relatively low temperatures, 56 structurally diverse multidentate ligands were screened in a model system that uses copper iodide in acetonitrile with potassium phosphate as the base. The ligands differed largely in their performance, but no privileged structural class could be identified.

scholarly journals Visible-Light Photoredox-Catalyzed C–O Bond Cleavage of Diaryl Ethers by Acridinium Photocatalysts at Room Temperature

2020 ◽  
Author(s):  
Fang-Fang Tan ◽  
Xiao-Ya He He ◽  
Wan-Fa Tian ◽  
Yang Li
Keyword(s):  
Visible Light ◽  
Room Temperature ◽  
Acid Catalysis ◽  
Bond Cleavage ◽  
Diphenyl Ether ◽  
Mechanistic Studies ◽  
Electrophilic Attack ◽  
One Pot ◽  
Diaryl Ethers ◽  
Diaryl Ether

Abstract We have developed visible-light photoredox-catalyzed C–O bond cleavage of diaryl ethers by an acidolysis with an aryl car-boxylic acid and a following one-pot hydrolysis. Two phenols are obtained from a diaryl ether at room temperature. The aryl carboxylic acid used for the acidolysis can be recovered. The key to success of the acidolysis is merging visible-light photore-dox catalysis with a new acridinium photocatalyst and Lewic acid catalysis with Cu(TMHD)2. Preliminary mechanistic studies indicate that the catalytic cycle occurs via a rare selective electrophilic attack of the generated aryl carboxylic radical on the electron-rich aryl ring of diphenyl ether. This transformation is applied to a gram-scale reaction and the model of 4-O-5 lignin linkages.

Enantioselective Synthesis of an Atropisomeric Diaryl Ether

2008 ◽  
Vol 120 (17) ◽  
pp. 3278-3281 ◽  
Author(s):  
Jonathan Clayden ◽  
Christopher P. Worrall ◽  
Wesley J. Moran ◽  
Madeleine Helliwell
Keyword(s):  
Enantioselective Synthesis ◽  
Diaryl Ether

scholarly journals Copper-catalyzed synthesis of phenol and diaryl ether derivatives via hydroxylation of diaryliodoniums

RSC Advances ◽  
2019 ◽  
Vol 9 (37) ◽  
pp. 21525-21529
Author(s):  
Lianbao Ye ◽  
Chao Han ◽  
Peiqi Shi ◽  
Wei Gao ◽  
Wenjie Mei
Keyword(s):  
Reaction Conditions ◽  
One Pot ◽  
Diaryl Ethers ◽  
Diaryl Ether

A copper-catalysed hydroxylation of diaryliodoniums to generate phenols and diaryl ethers allows the synthesis of diversely functionalized phenols under mild reaction conditions and prepares diaryl ethers in a one-pot operation.

Enantioselective Synthesis of an Atropisomeric Diaryl Ether

2008 ◽  
Vol 47 (17) ◽  
pp. 3234-3237 ◽  
Author(s):  
Jonathan Clayden ◽  
Christopher P. Worrall ◽  
Wesley J. Moran ◽  
Madeleine Helliwell
Keyword(s):  
Enantioselective Synthesis ◽  
Diaryl Ether

Catalytic enantioselective synthesis of indolizino[8,7-b]indole alkaloid derivatives based on the tandem reaction of tertiary enamides

2021 ◽  
Author(s):  
Xin-Ming Xu ◽  
Ming Xie ◽  
Jiazhu Li ◽  
Mei-Xiang Wang
Keyword(s):  
Indole Alkaloid ◽  
Enantioselective Synthesis ◽  
High Yield ◽  
Tandem Reaction ◽  
Indole Derivatives

An exquisite Pybox/Cu(OTf)2-catalyzed asymmetric tandem reaction of tertiary enamides was developed, which enabled the expeditious synthesis of indolizino[8,7-b]indole derivatives in high yield, excellent enantioselectivity and diastereoselectivity.

Chiral Organolithium Complexes:  The Effect of Ligand Structure on the Enantioselective Deprotonation of Boc-Pyrrolidine

1996 ◽  
Vol 61 (15) ◽  
pp. 5190-5190
Author(s):  
Donald J. Gallagher ◽  
Shengde Wu ◽  
Nikola A. Nikolic ◽  
Peter Beak
Keyword(s):  
Ligand Structure ◽  
Enantioselective Deprotonation
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