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Archive for the ‘Heck’ Category

Palladium/Copper Catalyzed Multi-Component Cascade

Posted by naturalproductman on October 21, 2010

Junliang Zhang and co-worker published in Chem Comm again on a three component coupling approach to synthesize tetrasubstituted furans.

three component coupling

Chem Comm paper

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Posted in cross coupling, Heck, Methodology, Multi-Component Coupling | Leave a Comment »

Carbonylative Heck

Posted by naturalproductman on August 30, 2010

Erik Alexanian and co-worker at the University of North Carolina at Chapel Hill have published in JACS on a carbonylative Heck reaction using palladium tetrakis(triphenyl)phosphine as the catalyst.  This reaction works best with non-polar solvents such as toluene because of a possible formation of phosphonium salts in polar solvents (THF:ACN).

palladium


JACS paper

Posted in Cascade Reactions, cross coupling, Heck, Methodology, Palladium, Transition Metal | Leave a Comment »

Synthesis of Rhazinilam

Posted by naturalproductman on August 27, 2010

Armen Zakarian and co-worker have published in UCSB on a Heck cyclization approach to access rhazinilam.

Heck

OL paper

Posted in Alkaloids, Asymmetric, Axial Chirality, cross coupling, Heck, Methodology, Palladium, Transition Metal | Leave a Comment »

A Heck Coupling

Posted by naturalproductman on June 18, 2010

Marco Ciofulini and co-workers at the University of British Columbia have published in Chemical Communications on a Pd catalyzed Csp2 carbon-aryl carbon bond forming process – ie:  Heck coupling – to form homotyrosine derivatives.

HECK

Chem Comm paper

Posted in C-H activation, Cascade Reactions, cross coupling, Heck, Methodology, Palladium, Transition Metal | Leave a Comment »

Aryl Diazonium Salts

Posted by naturalproductman on April 9, 2010

Francois-Xavier Felpin and co-workers from CNRS have recently reported in Chemistry a European Journal on a C-H activation of the beta-position of arylacrylates using an aryldiazonium salt.

HECK


Chemistry a European Journal paper

Posted in C-H activation, cross coupling, Heck, Methodology, Palladium, Transition Metal | Leave a Comment »

C-CN Cleavage with Rh

Posted by naturalproductman on March 25, 2010

Naoto Chatani and co-workers from Osaka University have recently reported in Organic Letters on a rhodium catalyzed C-C cleavage of an aryl cyanide substrate and coupled the aryl unit to an sp2-carbon.

aryl


OL paper

Posted in C-C Bond Breaking, cross coupling, Heck, Methodology, Mizoroki-Heck, Rhodium, Transition Metal | Leave a Comment »

Pd-Cascade

Posted by naturalproductman on March 2, 2010

Fabio Marinelli and co-workers at the Università dell’Aquila in Italy have recently published on a Pd-catalyzed cascade indole formation followed by Heck coupling to an alpha-iodo-enone to form a substituted indole.

pd

Tetrahedron paper

Posted in Cascade Reactions, cross coupling, Heck, Methodology, Palladium, Transition Metal | Leave a Comment »

Towards Chlorahololide A

Posted by naturalproductman on February 3, 2010

Fa-Jun Nan and co-worker at the Chinese Academy of Sciences have recently published in Tetrahedron Letters on their progress towards chlorahololide A.  An interesting structure in their route can be found in a Grignard addition of an bromo-magnesium bromo vinyl group that adds onto an aldehyde to ultimately form a bromo-butenolide.

chlorahololide A

TL paper

Posted in Cascade Reactions, cross coupling, Heck, Julia-Kocienski, Methodology, Named Reactions, Palladium, Ring forming, Sesquiterpenes, Transition Metal | Leave a Comment »

Stille-Heck

Posted by naturalproductman on February 1, 2010

A Stille-Heck Cascade reaction has been reported in Organic and Biomolecular Chemistry by Bernard Flynn and co-worker at the Monash Institute of Pharmaceutical Sciences in Australia for the application in the synthesis of frondosin.

stille heck

OBC paper

Posted in Conjugate Additions, cross coupling, Heck, Methodology, Palladium, Stille, Transition Metal | Leave a Comment »