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Archive for the ‘Iridium’ Category

C-O bond cleavage with Ir

Posted by naturalproductman on July 27, 2014

Alan Goldman and co-workers from Rutgers have reported in ACIE on an iridium pincer complex catalyzed C-O bond cleavage.

C-O

ACIE paper

Posted in Catalytic, Iridium, Methodology, 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 »

Silylation of C-H bonds

Posted by naturalproductman on May 6, 2014

I like this silylation of a C-H bond using an iridium catalyst. Very interesting from the lab of John Hartwig at Berkeley.

Ir

JACS paper

Posted in Asymmetric, C-H activation, Iridium, Methodology, Transition Metal | Leave a Comment »

Asperolide C synthesis

Posted by naturalproductman on September 27, 2013

Erick Carreira and co-workers have reported in ACIE on a synthesis of asperolide C using an iridium catalyzed poly-ene cascade cyclization.

Ir

ACIE paper

Posted in Asymmetric, Cascade Reactions, Iridium, Methodology, Total Synthesis, Transition Metal | Leave a Comment »

Glucose to hexanes

Posted by naturalproductman on January 23, 2013

Michael Gagne and co-workers at UNC used an iridium catalyst to reduce glucose to hexanes.

glucose

JACS paper

Posted in Environmental, Green chemistry, Iridium, Methodology, Transition Metal | Leave a Comment »

Photoredox catalysis

Posted by naturalproductman on February 11, 2012

Yoshiaki Nishibayashi and co-workers at the University of Tokyo have reported in JACS on the use of an iridium photocatalyst to form alpha-aminoalkyl radicals.

What is photoredox catalysis anyway?  I have always been turned away from this kind of reaction because it always looked like people lit up a light bulb right next to their reactions to run these reactions, but I guess more and more people are starting to develop it.  People use a catalyst with a special ligand that allows it to undergo a metal to ligand charge transfer in the presence of low energy visible light.  The excited catalyst accepts an electron from a donor source (such as Hunig’s base).  This may be the reaction of 2012.

alpha-aminoalkyl radicals

JACS paper

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

Fluorination of trichloroacetimidates

Posted by naturalproductman on November 12, 2011

Hien Nguyen and co-workers from the University of Illinois have reported in JACS on a fluorination reaction using iridium.  This substrate is a trichloroacetimidate that is usually found as a substrate in the Overman rearrangement.

fluoride

JACS paper

Posted in Iridium, Methodology, Transition Metal | Leave a Comment »

Ir cascade

Posted by naturalproductman on November 3, 2011

Shu-Li You and co-workers from Shanghai Institute of Organic Chemistry have reported in JACS on an iridium catalyzed coupling between amino-styrenes and allylic carbonates.

iridium

JACS paper

Posted in Alkaloids, Cascade Reactions, Iridium, Methodology, Transition Metal | Leave a Comment »

Reaction after another

Posted by naturalproductman on September 25, 2011

Corey Stephenson and colleague at Boston University have reported in Organic Letters on an iridium catalyzed tandem reaction using visible light – the reaction forms a divinyl cyclopropane intermediate that undergoes a Cope rearrangement.

cascade

OL paper

Posted in Cascade Reactions, Cope rearrangement, Iridium, Methodology, Named Reactions, Ring expansion, Ring forming, Transition Metal | Leave a Comment »

Allylic alcohol to alpha-fluoroketone

Posted by naturalproductman on August 22, 2011

Belen Martin Matute and co-workers at Stockholm University have reported in Synthesis on the transformation from an allylic alcohol to an alpha-fluoroketone using an iridium catalyst and Selectfluor as the fluorinating agent.
fluorination

Synthesis paper

Posted in Cascade Reactions, Iridium, Methodology, Transition Metal | Leave a Comment »

 
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