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Archive for the ‘Light Mediated’ Category

Photoredox cross-coupling

Posted by naturalproductman on August 31, 2015

Larry Overman and co-workers reported in JACS on a photoredox coupling between tertiary alcohols and electron deficient olefins.

JACS paper

Posted in cross coupling, Light Mediated, Methodology | Leave a Comment »

Blue-LED induced cascade

Posted by naturalproductman on July 17, 2015

Zhiyong Jiang and co-workers from Henan University have reported in ACIE on a radical cascade cyclization using blue light emitted diodes.

radical

ACIE paper

Posted in Cascade Reactions, Light Mediated, Methodology, Radical Chemistry | Leave a Comment »

C-C bond cleavage of alpha-aryl acetals

Posted by naturalproductman on July 13, 2015

Thomas Lectka and co-workers from Johns Hopkins University have reported in Chemical Science on an interesting C-C bond cleavage process.

C-C

Chemical Science paper

Posted in C-C Bond Breaking, Cascade Reactions, Light Mediated, Methodology | Leave a Comment »

Combining 2 concepts from sophmore organic chemistry (Sn2 and radical initiation)d

Posted by naturalproductman on July 11, 2015

The Finkesltein reaction is a straightforward Sn2 reaction – however, you don’t normally think of displacing an aromatic halide as an Sn2 reaction. Chao-Jun Li and co-workers at McGill University reported on the aromatic Finkelstein reaction using light.

 
light
 

JACS paper

Posted in Light Mediated, Methodology, Named Reactions, Radical Chemistry | Leave a Comment »

[2+2] stereochemistry

Posted by naturalproductman on April 12, 2015

Thorsten Bach and co-workers at Technische Universität München have reported in JACS on the stereochemistry of some [2+2] reactions.

2+2
JACS paper

Posted in Light Mediated, Methodology, [2+2] | Leave a Comment »

Light mediated radical reaction

Posted by naturalproductman on April 12, 2015

Paolo Melchiorre and co-workers from ICIQ have reported in JACS on a light mediated alkylation of aldehydes.

light
JACS paper

Posted in Light Mediated, Methodology | Leave a Comment »

Aryl halide couplings with Sp3-carbons

Posted by naturalproductman on July 27, 2014

Gary Molander and colleagues reported in Science on a photoredox nickel dual catalysis for a cross coupling reaction between an sp3-hybridized organoboron and an aryl halide.

Science paper (Molander)

In the same issue, David Macmillan and co-workers have reported on a photoredox reaction involving a nickel catalyzed coupling between an sp3-alpha-carboxyl and an aryl halide.

Science paper (Macmillan)

 

Posted in Cascade Reactions, cross coupling, Light Mediated, Methodology, Nickel, Transition Metal | Leave a Comment »

Indole alkaloid synthesis

Posted by naturalproductman on July 15, 2014

Corey Stephenson and colleague at the University of Michigan have reported in JACS on the synthesis of pseudotabersonine. A mental roadblock for me was when I was looking at the paper, I was trying to find the structure of catalyst 5, which was the iridium catalyst used for a ring opening reaction, but just found the number 5 in the scheme. Within the text of the paper however it says Ir(dF(CF3)ppy)2(dtbbpy)PF6, which was cited with a Sigma Aldrich catalog number.

 

photoredox

JACS paper

Posted in Alkaloids, Indoles, Iridium, Light Mediated, Methodology, Transition Metal | Leave a Comment »

Asymmetric [2+2]

Posted by naturalproductman on April 25, 2014

Tehshik Yoon and co-workers published in Science on an enantioselective [2+2] reaction.

Science paper

Posted in Asymmetric, Cycloaddition, Light Mediated, Methodology, Pericyclic reactions, [2+2] | Leave a Comment »

17-Deoxyprovidencin synthesis

Posted by naturalproductman on March 7, 2014

Johann Mulzer and co-workers have reported in ACIE on the synthesis of 17-deoxyprovidencin.

17-deoxyprovidencin
ACIE paper

Posted in Asymmetric, Light Mediated, Methodology, Total Synthesis | Leave a Comment »

 
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