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Archive for the ‘Iridium’ Category

Another thing to add to the dynamic kinetic resolution book

Posted by naturalproductman on April 12, 2015

Yu Zhao and co-workers from the National University of Singapore have reported in JACS on an iridium catalyzed dynamic kinetic resolution of a diastereomeric mixture of alcohols to chiral amines using a phosphoric acid ligand.

amine

JACS paper

Posted in Iridium, Kinetic resolution, Transition Metal | Leave a Comment »

Antroquinonol synthesis

Posted by naturalproductman on February 22, 2015

Chinpiao Chen and co-worker from National Dong Hwa University have reported in Organic Letters on the syntheses of antroquinononol and antroquinonol D.

antroquinonol

OL paper

Posted in Iridium, Sesquiterpenes, Total Synthesis, Transition Metal | Leave a Comment »

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 »

 
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