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

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.

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

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.

scholarly journals Alkene Carboarylation through Catalyst‐Free, Visible Light‐Mediated Smiles Rearrangement

2019 ◽  
Vol 25 (8) ◽  
pp. 1927-1930 ◽  
Author(s):  
David M. Whalley ◽  
Hung A. Duong ◽  
Michael F. Greaney
Keyword(s):  
Visible Light ◽  
Smiles Rearrangement ◽  
Catalyst Free

scholarly journals Photocatalyzed cycloaromatization of vinylsilanes with arylsulfonylazides

2021 ◽  
Vol 12 (1) ◽  
Author(s):  
Fengjuan Chen ◽  
Youxiang Shao ◽  
Mengke Li ◽  
Can Yang ◽  
Shi-Jian Su ◽  
...  
Keyword(s):  
Density Functional Theory ◽  
Biological Activity ◽  
Reaction Mechanism ◽  
Physicochemical Properties ◽  
Visible Light ◽  
Density Functional ◽  
Covalent Radius ◽  
Smiles Rearrangement ◽  
Functional Theory ◽  
Energy Profiles

AbstractSila-molecules have recently attracted attention due to their promising applications in medical and industrial fields. Compared with all-carbon parent compounds, the different covalent radius and electronegativity of silicon from carbon generally endow the corresponding sila-analogs with unique biological activity and physicochemical properties. Vinylsilanes feature both silyl-hyperconjugation effect and versatile reactivities, developing vinylsilane-based Smiles rearrangement will therefore provide an efficient platform to assemble complex silacycles. Here we report a practical Ir(III)-catalyzed cycloaromatization of ortho-alkynylaryl vinylsilanes with arylsulfonyl azides for delivering naphthyl-fused benzosiloles under visible-light photoredox conditions. The combination of experiments and density functional theory (DFT) energy profiles reveals the reaction mechanism involving α-silyl radical Smiles rearrangement.

scholarly journals A visible light-mediated, decarboxylative, desulfonylative Smiles rearrangement for general arylethylamine syntheses

2020 ◽  
Vol 56 (77) ◽  
pp. 11493-11496 ◽  
Author(s):  
David M. Whalley ◽  
Hung A. Duong ◽  
Michael F. Greaney
Keyword(s):  
Amino Acid ◽  
Visible Light ◽  
Unnatural Amino Acid ◽  
Smiles Rearrangement ◽  
Biologically Relevant ◽  
Wide Range

A decarboxylative, desulfonylative Smiles rearrangement is reported for the synthesis of a wide range of biologically relevant arylethylamines, including fluorinated phenylethylamines, heterocyclic amphetamines and an unnatural amino acid.

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