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Archive for the ‘C-C Bond Breaking’ Category

This reaction breaks C-C bonds.

C-C bond cleavage with titanium

Posted by naturalproductman on August 28, 2014

Zhaomin Hou and co-workers at RIKEN (Saitama, JP) have reported in Nature on a titanium hydride complex that cleaves carbon-carbon bonds.

 

Nature paper

Posted in C-C Bond Breaking, Methodology, Titanium, Transition Metal | Leave a Comment »

C-H vs. C-C

Posted by naturalproductman on November 16, 2012

Chisato Mukai and co-workers from Kanazawa University have reported in JACS on a rhodium catalyzed transformation that either results in a C-C bond cleavage or C-H bond activation reaction depending on the ligand.

C-H

JACS paper

Posted in C-C Bond Breaking, C-H activation, Methodology, Rhodium, Transition Metal | Leave a Comment »

C-C bond breaking mechanism

Posted by naturalproductman on November 8, 2012

Here’s an interesting paper where the authors used 18O2 to label one of the oxygens found in the product to investigate the mechanism. Now I’m going to be a little bit critical here but in the supporting information they put the 18O-label on the carbonyl oxygen but in the manuscript they don’t know if it is on the O-benzyl of the ester or the carbonyl oxygen. Moreover the abstract figure shows that the 18O is on the carbonyl oxygen but they really don’t know. It’s a bit deceiving in the paper because it kind of sounds like they determined it through GC-MS but in the supporting information I could not find the GC-MS trace. I guess there is a limitation in analytical technology to determine the position of the 18O. But still it is not clear from the paper that they don’t know which position the 18-oxygen is.

O

ACIE paper

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

Oxycyanation of olefins

Posted by naturalproductman on April 10, 2012

Yoshiaki Nakao and co-workers from Kyoto University have reported in JACS on an intramolecular palladium catalyzed oxycyanation.

palladium

JACS paper

Posted in C-C Bond Breaking, Cascade Reactions, Methodology, Palladium, Transition Metal | Leave a Comment »

Alkyl chlorides from carboxylic acids

Posted by naturalproductman on February 22, 2012

Chaozhong Li and co-workers from Shanghai Institute of Organic Chemistry have reported in JACS on a silver catalyzed decarboxylative chlorination.

chloride

JACS paper

Posted in C-C Bond Breaking, Methodology, Silver, Transition Metal | Leave a Comment »

C-C bond cleavage via SnCl4

Posted by naturalproductman on December 2, 2011

Matthias Brewer and co-workers at the University of Vermont have reported in Organic Letters on a tin promoted C-C bond cleavage.

carbene

OL paper

Posted in C-C Bond Breaking, Cascade Reactions, Methodology, Ring expansion, Ring Opening | Leave a Comment »

Poof be gone

Posted by naturalproductman on September 18, 2011

Alexander Butin and co-workers have reported in Tetrahedron Letters on the loss of a vinyl methyl ketone group from an indole.

acetyl vinyl

TL paper

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

C-C bond coupling via C-C bond breaking

Posted by naturalproductman on September 13, 2011

Zhang-Jie Shi and co-workers at Peking University have reported in JACS on a rhodium catalyzed C-C bond coupling reaction by cleaving the aryl-carbon bond in secondary aryl methanols.

arylmethanol

JACS paper

Posted in C-C Bond Breaking, C-H activation, Methodology, Rhodium, Transition Metal | Leave a Comment »

Introducing a trifluoro group

Posted by naturalproductman on August 26, 2011

Erick Carreira and co-worker have reported in ACIEE on a way to introduce a trifluoroethyl group onto either a cyclic ketone or aldehyde using a Zr-catalyst.

trifluoro

ACIEE paper

Posted in C-C Bond Breaking, Cascade Reactions, Methodology, Transition Metal, Zirconium | Leave a Comment »

Breaking the C-C triple bond

Posted by naturalproductman on August 22, 2011

Igor Alabugin and co-workers from Florida State have reported in JOC on a double Michael reaction that cleaves the C-C triple bond of an alkynone.

cleave alkyne

JOC paper

Posted in C-C Bond Breaking, Cascade Reactions, Mannich, Methodology, Michael, Named Reactions, Pericyclic reactions, Sigmatropic Rearrangements | Leave a Comment »

 
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