Naturalproductman’s Blog

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Archive for the ‘Carbene’ Category

Substituted benzaldehydes via NHCs

Posted by naturalproductman on March 25, 2015

David Lupton and co-workers at Monash University have reported in Chemical Science on a method to synthesize substituted benzenes from acyclic precursors.
benzene
Chemical Science paper

Posted in Carbene, Cascade Reactions, Methodology | Leave a Comment »

B-H insertions

Posted by naturalproductman on March 5, 2015

Ming-Hua Xu and co-workers from the Chinese Academy of Sciences have reported in JACS on a rhodium catalyzed transformation of a diazo to an organoborane.

B-H

JACS paper

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

NHC-catalyzed [4+2]

Posted by naturalproductman on October 4, 2014

David Lupton and co-worker at Monash University have reported in JACS on an NHC-catalyzed [4+2] reaction.
4+2

JACS paper

Posted in Carbene, Cascade Reactions, Methodology | Leave a Comment »

Dihydropyran access

Posted by naturalproductman on May 6, 2014

Carlos Saa and co-workers at Universidad de Santiago de Compostela have reported in ACIE on a reaction involving a ruthenium cascade followed by C-O formation to form dihydropyrans.

ruthenium
ACIE paper

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

Pyridines from 2H-azirines

Posted by naturalproductman on January 16, 2013

Cheol-Min Park and co-workers from Nanyang Technological University in Singapore have reported in ACIE on the synthesis of pyridines from 2H-azirines.

carbene

ACIE paper

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

Juglomycin A synthesis

Posted by naturalproductman on November 12, 2012

Rodney Fernandes and co-workers from IIT Bombay have reported in JOC on a chromium carbene approach to access juglomycin.

chromium

JOC paper

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

Pyridine synthesis

Posted by naturalproductman on October 16, 2012

Cheol-Min Park and co-workers at Nanyang Technological University have reported in Chem Comm on a method for synthesis of pyridines through N-O bond cleavage using a carbenoid precursor.

pyridine

Chem Comm paper

Posted in Carbene, Cascade Reactions, Methodology | Leave a Comment »

Friedel-Crafts cascade

Posted by naturalproductman on April 4, 2012

Arun Ghosh and co-workers from Purdue have reported in Organic Letters on a Friedel-Crafts cascade to form a seven membered ring.
seven

OL paper

Posted in Carbene, Cascade Reactions, Friedel-Crafts, Methodology, Named Reactions, Seven-Membered Rings, Titanium, Transition Metal | Leave a Comment »

Loss of diazo group cascade

Posted by naturalproductman on March 29, 2012

Claude Spino and co-workers at Universite de Sherbrooke have reported in JACS on a [4+1] cascade.  A loss of a diazo group involved, hmm…reminds me of some of Dale Boger’s work.
diazo cascade

JACS paper

Posted in Carbene, Cascade Reactions, Methodology | Leave a Comment »

Loss of 2 x N2 to form carbenes

Posted by naturalproductman on February 29, 2012

Duncan Wardrop and co-worker from the University of Illinois in Chicago have reported in Organic Letters on an interesting approach to form a carbene by presumably forming a tetraazafulvene intermediate, which breaks down to the carbene by losing two molecules of nitrogen (ie:  N2).  At first I wondered how scary this reaction is because of the gain of entropy, but it looks pretty straight forward:  they just add DIC (diisopropylcarbodiimide) to the tetrazole and then load the reaction mixture directly on a column for purification.

Loss of N2

OL paper

Posted in Carbene, Cascade Reactions, Methodology | Leave a Comment »

 
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