Ynamide Smiles Rearrangement Triggered by Visible-Light-Mediated Regioselective Ketyl–Ynamide Coupling: Rapid Access to Functionalized Indoles and Isoquinolines

2020 ◽  
Vol 142 (7) ◽  
pp. 3636-3644 ◽  
Author(s):  
Ze-Shu Wang ◽  
Yang-Bo Chen ◽  
Hao-Wen Zhang ◽  
Zhou Sun ◽  
Chunyin Zhu ◽  
...  
Keyword(s):  
Visible Light ◽  
Smiles Rearrangement ◽  
Rapid Access

Visible-light-induced remote C(sp3)-H sulfonylvinylation: assembly of cyanoalkylated vinyl sulfones

2021 ◽  
Author(s):  
Ping Bao ◽  
Feiyan Yu ◽  
Fu-Sheng He ◽  
Zhimei Tang ◽  
Wei-Ping Deng ◽  
...  
Keyword(s):  
Visible Light ◽  
Rapid Access ◽  
Three Component Reaction ◽  
Propargyl Alcohols

A photoinduced sulfonylvinylation of unactivated C(sp3)-H bond through a three-component reaction of propargyl alcohols, potassium metabisulfite and cycloketone oxime esters is developed. This approach enables rapid access to cyanoalkylated vinyl...

A Visible-Light-Mediated Radical Smiles Rearrangement and its Application to the Synthesis of a Difluoro-Substituted Spirocyclic ORL-1 Antagonist

2015 ◽  
Vol 127 (49) ◽  
pp. 15111-15115 ◽  
Author(s):  
James J. Douglas ◽  
Haley Albright ◽  
Martin J. Sevrin ◽  
Kevin P. Cole ◽  
Corey R. J. Stephenson
Keyword(s):  
Visible Light ◽  
Smiles Rearrangement

scholarly journals A Visible-Light-Mediated Radical Smiles Rearrangement and its Application to the Synthesis of a Difluoro-Substituted Spirocyclic ORL-1 Antagonist

2015 ◽  
Vol 54 (49) ◽  
pp. 14898-14902 ◽  
Author(s):  
James J. Douglas ◽  
Haley Albright ◽  
Martin J. Sevrin ◽  
Kevin P. Cole ◽  
Corey R. J. Stephenson
Keyword(s):  
Visible Light ◽  
Smiles Rearrangement

Preparative Scale Demonstration and Mechanistic Investigation of a Visible Light-Mediated Radical Smiles Rearrangement

2016 ◽  
Vol 20 (7) ◽  
pp. 1148-1155 ◽  
Author(s):  
James J. Douglas ◽  
Martin J. Sevrin ◽  
Kevin P. Cole ◽  
Corey R. J. Stephenson
Keyword(s):  
Visible Light ◽  
Smiles Rearrangement ◽  
Preparative Scale ◽  
Mechanistic Investigation

scholarly journals Visible light amination/Smiles cascade: access to phthalazine derivatives

2016 ◽  
Vol 7 (8) ◽  
pp. 5002-5006 ◽  
Author(s):  
Etienne Brachet ◽  
Leyre Marzo ◽  
Mohamed Selkti ◽  
Burkhard König ◽  
Philippe Belmont
Keyword(s):  
Visible Light ◽  
Cascade Reaction ◽  
Visible Light Photocatalysis ◽  
Smiles Rearrangement

We report the synthesis of various phthalazines via a new cascade reaction, initiated by visible light photocatalysis, involving a radical hydroamination reaction followed by a radical Smiles rearrangement.

Visible-light-induced multicomponent cascade cycloaddition involving N-propargyl aromatic amines, diaryliodonium salts and sulfur dioxide: rapid access to 3-arylsulfonylquinolines

2018 ◽  
Vol 54 (11) ◽  
pp. 1335-1338 ◽  
Author(s):  
Deli Sun ◽  
Kun Yin ◽  
Ronghua Zhang
Keyword(s):  
Sulfur Dioxide ◽  
Visible Light ◽  
Aromatic Amines ◽  
Eosin Y ◽  
Rapid Access ◽  
Diaryliodonium Salts

A visible-light-induced, Eosin Y catalyzed three-component synthesis of 3-arylsulfonylquinoline derivatives through N-propargyl aromatic amines, diaryliodonium salts and sulfur dioxide has been discovered.

Acylation of indoles via photoredox catalysis: a route to 3-acylindoles

2016 ◽  
Vol 18 (5) ◽  
pp. 1201-1205 ◽  
Author(s):  
Lijun Gu ◽  
Cheng Jin ◽  
Jiyan Liu ◽  
Hongtao Zhang ◽  
Minglong Yuan ◽  
...  
Keyword(s):  
Visible Light ◽  
Room Temperature ◽  
Bond Activation ◽  
Photoredox Catalysis ◽  
Rapid Access

A visible-light-catalyzed synthesis of 3-acylindoles from simple indoles and α-oxo acids at room temperature has been discovered. This method offers rapid access to 3-acylindoles through C–C and C–H bond activation.

Asymmetric, visible light-mediated radical sulfinyl-Smiles rearrangement to access all-carbon quaternary stereocentres

2021 ◽  
Vol 13 (4) ◽  
pp. 327-334 ◽  
Author(s):  
Cédric Hervieu ◽  
Mariia S. Kirillova ◽  
Tatiana Suárez ◽  
Marco Müller ◽  
Estíbaliz Merino ◽  
...  
Keyword(s):  
Visible Light ◽  
Smiles Rearrangement

scholarly journals Cerium photocatalyzed radical smiles rearrangement of 2-aryloxybenzoic acids

RSC Advances ◽  
2021 ◽  
Vol 11 (41) ◽  
pp. 25207-25210
Author(s):  
Alisha Rani Tripathy ◽  
Girish Suresh Yedase ◽  
Veera Reddy Yatham
Keyword(s):  
Carboxylic Acid ◽  
Visible Light ◽  
Acid Group ◽  
Aryl Ether ◽  
Carboxylic Acid Group ◽  
Smiles Rearrangement ◽  
Visible Light Driven

Visible light-driven CeCl3-mediated aryl migration from an aryl ether to a carboxylic acid group through radical-Smiles rearrangement is reported.

scholarly journals A photoredox-neutral Smiles rearrangement of 2-aryloxybenzoic acids

2017 ◽  
Vol 15 (45) ◽  
pp. 9680-9684 ◽  
Author(s):  
Jose. C. Gonzalez-Gomez ◽  
Nieves P. Ramirez ◽  
Teresa Lana-Villarreal ◽  
Pedro Bonete
Keyword(s):  
Visible Light ◽  
Noble Metals ◽  
Room Temperature ◽  
Smiles Rearrangement

The radical Smiles rearrangement of 2-aryloxybenzoic acids can be promoted by visible light at room temperature, in the presence of air and water, and free of noble metals.

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