scholarly journals Nickel-catalyzed reductive cleavage of aryl alkyl ethers to arenes in absence of external reductant

2015 ◽  
Vol 6 (6) ◽  
pp. 3410-3414 ◽  
Author(s):  
Mamoru Tobisu ◽  
Toshifumi Morioka ◽  
Akimichi Ohtsuki ◽  
Naoto Chatani
Keyword(s):  
Nickel Catalyst ◽  
Alkoxy Group ◽  
Reductive Cleavage ◽  
Alkyl Ethers ◽  
Aryl Ethers

A nickel catalyst for reductive cleavage of aryl ethers in the absence of an external reductant is developed. The alkoxy group of the substrate serves as an internal reductant.

Boron insertion into alkyl ether bonds via zinc/nickel tandem catalysis

Science ◽  
2021 ◽  
Vol 372 (6538) ◽  
pp. 175-182
Author(s):  
Hairong Lyu ◽  
Ilia Kevlishvili ◽  
Xuan Yu ◽  
Peng Liu ◽  
Guangbin Dong
Keyword(s):  
Nickel Catalyst ◽  
Bioactive Compounds ◽  
Cyclic Ethers ◽  
Alkyl Ether ◽  
Tandem Catalysis ◽  
Mechanistic Studies ◽  
Alkyl Ethers ◽  
Nitrogen Substitution ◽  
Zinc Nickel

Mild methods to cleave the carbon-oxygen (C−O) bond in alkyl ethers could simplify chemical syntheses through the elaboration of these robust, readily available precursors. Here we report that dibromoboranes react with alkyl ethers in the presence of a nickel catalyst and zinc reductant to insert boron into the C−O bond. Subsequent reactivity can effect oxygen-to-nitrogen substitution or one-carbon homologation of cyclic ethers and more broadly streamline preparation of bioactive compounds. Mechanistic studies reveal a cleavage-then-rebound pathway via zinc/nickel tandem catalysis.

ChemInform Abstract: Functionalization of the Alkoxy Group of Alkyl Aryl Ethers. Demethylation, Alkylthiolation and Reduction of 5-Methoxyindoles.

ChemInform ◽  
2010 ◽  
Vol 26 (19) ◽  
pp. no-no
Author(s):  
C. CAUBERE ◽  
P. CAUBERE ◽  
P. RENARD ◽  
J.-G. BIZOT-ESPIART ◽  
S. IANELLI ◽  
...  
Keyword(s):  
Alkoxy Group ◽  
Alkyl Aryl ◽  
Aryl Ethers ◽  
Alkyl Aryl Ethers

ChemInform Abstract: Nickel-Catalyzed Reductive Cleavage of Aryl Alkyl Ethers to Arenes in Absence of External Reductant.

ChemInform ◽  
2015 ◽  
Vol 46 (37) ◽  
pp. no-no
Author(s):  
Mamoru Tobisu ◽  
Toshifumi Morioka ◽  
Akimichi Ohtsuki ◽  
Naoto Chatani
Keyword(s):  
Reductive Cleavage ◽  
Alkyl Ethers

Electrostatic and Electrophilic Catalysis in the Reductive Cleavage of Alkyl Aryl Ethers. The Influence of Ion Pairing on the Regioselectivity

2000 ◽  
Vol 65 (2) ◽  
pp. 322-331 ◽  
Author(s):  
Francisco Casado ◽  
Luisa Pisano ◽  
Maria Farriol ◽  
Iluminada Gallardo ◽  
Jordi Marquet ◽  
...  
Keyword(s):  
Ion Pairing ◽  
Reductive Cleavage ◽  
Alkyl Aryl ◽  
Aryl Ethers ◽  
Alkyl Aryl Ethers

scholarly journals Lewis-base silane activation: from reductive cleavage of aryl ethers to selective ortho-silylation

2013 ◽  
Vol 4 (4) ◽  
pp. 1640 ◽  
Author(s):  
Alexey Fedorov ◽  
Anton A. Toutov ◽  
Nicholas A. Swisher ◽  
Robert H. Grubbs
Keyword(s):  
Reductive Cleavage ◽  
Lewis Base ◽  
Aryl Ethers

ChemInform Abstract: Regio- and Stereochemistry of Na-Mediated Reductive Cleavage of Alkyl Aryl Ethers.

ChemInform ◽  
2015 ◽  
Vol 46 (18) ◽  
pp. no-no
Author(s):  
Ugo Azzena ◽  
Massimo Carraro ◽  
Claudia Meloni ◽  
Irene Murgia ◽  
Luisa Pisano ◽  
...  
Keyword(s):  
Reductive Cleavage ◽  
Alkyl Aryl ◽  
Aryl Ethers ◽  
Alkyl Aryl Ethers

scholarly journals Reductive Cleavage of Aryl-O-and Aryl-CI- Bonds by C8K: a Potential Method for the Degradation of Dioxins

1988 ◽  
Vol 43 (9) ◽  
pp. 1211-1212 ◽  
Author(s):  
Manfred Lissel ◽  
Jürgen Kottmann ◽  
Dov Tamarkin ◽  
Mordechai Rabinovitz
Keyword(s):  
Potential Method ◽  
Reductive Cleavage ◽  
Aryl Halides ◽  
Aryl Ethers

Abstract Potassium graphite intercalate in THF is a reagent for the reduction of aryl halides and the reductive cleavage of aryl ethers.

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