Naturalproductman’s Blog

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Archive for the ‘C-X Bond Breaking’ Category

Where X does not equal C

C-H vs. C-S Activation

Posted by naturalproductman on March 18, 2011

Datong Song and co-worker at the University of Toronto have reported in Organometallics on C-S and C-H activation reactions using either a platinum (0) or platinum (II) metal, respectively.

C-S

Organometallics paper

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

Benzynes and Alkynyl Ethers

Posted by naturalproductman on February 3, 2011

Enrique Guitian and colleagues at Universidade de Santiago de Compostela have published in Organic Letters on a reaction between a benzyne and an alkynyl ether.

 

alkyne

 

OL paper

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

Nickel Catalyzed Deoxygenation

Posted by naturalproductman on January 24, 2011

Naoto Chatani and co-workers at Osaka University have published in Chem Comm on a nickel catalyzed deoxygenation process.

deoxygenation

 

Chem Comm paper

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

TMDSO as the Hydrogen Source

Posted by naturalproductman on September 15, 2010

Ruben Martin and co-worker from ICIQ in Spain have published in JACS on a nickel catalyzed C-O bond cleavage using tetramethyldisiloxane (TMDSO) as the hydride source.

silica

JACS paper

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

Circumdatin Synthesis

Posted by naturalproductman on August 2, 2010

Narshinha Argade and co-worker at CSIR have published in Organic Letters on a copper catalyzed approach to form the N-aryl bond in circumdatin.

circumdatin


OL paper

Posted in Alkaloids, C-X Bond Breaking, Copper, Methodology, Transition Metal | Leave a Comment »

Smiles Rearrangement Followed by Sonogashira-Cyclization Cascade

Posted by naturalproductman on July 10, 2010

Roberto Sanz and co-workers from Universidad de Burgos have published in Organic and Biomolecular Chemistry on a method to access indole rings starting from phenylcarbamates.  The nitrogen of the indole ring is introduced via Smiles rearrangement of the carbamate-protected phenol to exchange the oxygen to nitrogen.

Smiles
OBC paper

Posted in C-X Bond Breaking, Cascade Reactions, cross coupling, Methodology, Named Reactions, Ring forming, Smiles rearrangement, Sonogashira | Leave a Comment »

Palladium Cascade

Posted by naturalproductman on July 9, 2010

Yimin Hu and co-workers at Anhui Normal University have published in the European Journal of Organic Chemistry on a palladium catalyzed cascade reaction.  Mechanistically it involves an oxidative addition followed by two carbopalladations and a single C-H activation step.

palladium

European JOC paper

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

Iron Demethylation

Posted by naturalproductman on June 21, 2010

Peter Scammells and co-workers at Monash University have published in JOC on an iron mediated C-N cleavage reaction using first mCPBA to oxidize the nitrogen followed by iron to reduce to the demethylated free amine.

nitrogen

JOC paper

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

Vinyl Bromo Ketones to Furans

Posted by naturalproductman on June 9, 2010

Chaozhong Li and co-workers from Shanghai Institute of Organic Chemistry have published in Tetrahedron Letters on the synthesis of substituted furans from vinyl bromo ketones using a copper catalyst.

vinyl bromo

TL paper

Posted in C-X Bond Breaking, Cascade Reactions, Copper, Methodology, Ring forming, Transition Metal | Leave a Comment »

Enamine Synthesis

Posted by naturalproductman on June 7, 2010

Chanjuan Xi and co-workers at Tsinghua University have published in China have published in Organic Letters on a copper catalyzed C-N bond formation to make enamines.

enamine

OL paper

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