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Archive for the ‘C-X Bond Breaking’ Category

Where X does not equal C

Ni-catalyzed C-B bond from C-N bond

Posted by naturalproductman on April 4, 2014

Naoto Chatani and co-workers from Osaka University have reported in JACS on a useful transformation of a reductive cleavage of a C-N bond to form C-B and C-H bonds.

Ni

JACS paper

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

C-S addition onto a terminal alkyne with rhenium

Posted by naturalproductman on November 21, 2012

Kazuhiko Takai and co-workers have reported in Organic Letters on a rhenium catalyzed C-S bond addition onto a terminal alkyne. We don’t usually see much of rhenium chemistry out there, but when there is something, it seems to be interesting.

C-S

OL paper

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

Erythromycin A deoxygenation

Posted by naturalproductman on February 11, 2012

Scott Miller and colleague have reported in ACIEE on a site selective deoxygenation of erythromycin A.

erythromycin A

ACIEE paper

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

MCC with benzynes

Posted by naturalproductman on September 24, 2011

Hiroto Yoshida and co-workers at Hiroshima University have reported in ACIEE on a three component coupling between a benzyne, aryl or alkynyl bromide and nucleophile to form substituted aryl bromides.  What’s fascinating is that the aryl or alkynyl group transfers to the nucleophile.

benzyne

ACIEE paper

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

Triazole ring opening

Posted by naturalproductman on September 22, 2011

Christopher Bielawski and co-workers at UT Austin have reported in Science on the ring opening of a triazole ring, which is usually viewed as the product of a click reaction.

 

Science paper

Posted in C-X Bond Breaking, Methodology, Ring Opening | Leave a Comment »

Alkenes + Alcohols = C-C bond + loss of water

Posted by naturalproductman on September 20, 2011

Chae Yi and co-workers at Marquette University have reported in Science on a cationic ruthenium complex that forms a C-C bond between an alcohol and an alkene with a net loss of a water molecule.

Science paper

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

Csp3-Csp3 bond coupling reaction

Posted by naturalproductman on May 10, 2011

Gregory Fu and co-workers have reported in JACS on a nickel catalyzed coupling between an alkyl amino halide and an alkyl borane.

Suzuki

JACS paper

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

From aryl halides to phenols

Posted by naturalproductman on May 9, 2011

Govindas Sekar and co-workers from IIT Madras have reported in Chem Comm on a Cu-catalyzed C-X activation converting an aryl halide into a phenol using KOH as the oxygen source.  They used glucose as the ligand.

C-X

Chem Comm paper

Posted in C-X Bond Breaking, Copper, Methodology, Transition Metal | 1 Comment »

Ni-catalyzed C-O bond cleavage

Posted by naturalproductman on April 26, 2011

John Hartwig and colleague have reported in Science on a nickel catalyzed C-O bond cleavage of an ether.

Science paper

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

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

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

 
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