Silver oxide(I) promoted Conia-ene/radical cyclization for a straightforward access to furan derivatives

2022 ◽  
Author(s):  
Bao Yu ◽  
mohamed selkti ◽  
Janick Ardisson ◽  
Marie-Isabelle Lannou ◽  
Geoffroy Sorin
Keyword(s):  
Silver Oxide ◽  
Radical Cyclization ◽  
Furan Derivatives ◽  
Ene Reaction ◽  
Mechanistic Investigations

A novel access to fused furan cores using silver oxide(I) has been developed. Mechanistic investigations would indicate the involvement of a Conia-ene reaction/radical cyclization for an expedient path to complex...

Mechanistic Investigations into the Enantioselective Conia-Ene Reaction Catalyzed by Cinchona-Derived Amino Urea Pre-Catalysts and CuI

2013 ◽  
Vol 19 (42) ◽  
pp. 14286-14295 ◽  
Author(s):  
Filippo Sladojevich ◽  
Ángel L. Fuentes de Arriba ◽  
Irene Ortín ◽  
Ting Yang ◽  
Alessandro Ferrali ◽  
...  
Keyword(s):  
Ene Reaction ◽  
Mechanistic Investigations

Mn(III)-Mediated Facile Access to Polysubstituted α-Naphthols from β-Keto Ester Derivatives and Terminal Alkynes

Synthesis ◽  
2020 ◽  
Vol 52 (13) ◽  
pp. 1959-1968
Author(s):  
Yuzhu Yang ◽  
Weidong Pan ◽  
Lisheng He ◽  
Fei Li ◽  
Xiaolan Liu
Keyword(s):  
Radical Cyclization ◽  
Terminal Alkynes ◽  
Keto Ester ◽  
Keto Esters ◽  
Mild Conditions ◽  
Cyclization Process ◽  
Reaction Proceeds ◽  
Mechanistic Investigations

A novel manganese-mediated reaction for the synthesis of polysubstituted α-naphthols has been developed from β-keto esters and terminal alkynes. This system holds the advantages of readily available starting materials and mild conditions. Mechanistic investigations revealed that this reaction proceeds via a tandem radical cyclization process.

Study on the "Tin-Ene" Reaction of α-Bromoacetophenone and Metallic Tin With Aldehydes

1996 ◽  
Vol 24 (4) ◽  
pp. 769-775
Author(s):  
Jing-Yao Zhou ◽  
Yu Jia ◽  
Qiu-Yi Shao ◽  
Shi-Hui Wu
Keyword(s):  
Ene Reaction

Three-Component [1+1+1] Cyclopropanation with Ruthenium(II)

2018 ◽  
Author(s):  
Tanner C. Jankins ◽  
Robert R. Fayzullin ◽  
Eugene Khaskin
Keyword(s):  
Quaternary Carbon ◽  
Poor Control ◽  
One Step ◽  
Synthetic Routes ◽  
Mechanistic Investigations ◽  
Chiral Centers ◽  
Metal Catalyzed ◽  
The Right ◽  
Substituted Cyclopropanes

We report a one-step, Ru(II)-catalyzed cyclopropanation reaction that is conceptually different from the previously reported protocols that include Corey-Chaykovsky, Simmons-Smith, and metal catalyzed carbene attack on olefins. Under the current protocol, various alcohols are transformed into sulfone substituted cyclopropanes with excellent isolated yields and diastereoselectivities. This new reaction forms highly congested cyclopropane products with three new C–C bonds, three or two new chiral centers and one new quaternary carbon center. 22 examples of isolated substrates are given. Previously reported synthetic routes for similar substrates are all multi-step, linear routes that proceed with overall low yields and poor control of stereochemistry. Experimental mechanistic investigations suggest initial metal-catalyzed dehydrogenation of the alcohol substrate and catalyst independent stepwise attack of two equivalents of sulfone on the aldehyde under basic conditions. While the Ru(II) is only responsible for the initial dehydrogenation step, the rate of aldehyde formation is crucial to maintaining the right balance of intermediates needed to afford the cyclopropane product.

Visible Light-Induced Sulfonylation/Arylation of Styrenes in a Double Radical Three-Component Photoredox Reaction

2019 ◽  
Author(s):  
Benjamin Lipp ◽  
Lisa Marie Kammer ◽  
Murat Kucukdisli ◽  
Adriana Luque ◽  
Jonas Kühlborn ◽  
...  
Keyword(s):  
Visible Light ◽  
Radical Formation ◽  
Three Component Reaction ◽  
Broad Variety ◽  
Styrene Derivatives ◽  
Mechanistic Investigations

Simultaneous sulfonylation/arylation of styrene derivatives is achieved in a photoredox-catalyzed three-component reaction using visible light. A broad variety of difunctionalized products is accessible in mostly excellent yields and high diastereoselectivity. The developed reaction is scalable and suitable for the modification of styrene-functionalized biomolecules. Mechanistic investigations suggest the transformation to be operating through a designed sequence of radical formation and radical combination.<br>

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