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Archive for the ‘Suzuki-Miyaura’ Category

Enantiospecific Suzuki-Miyaura

Posted by naturalproductman on December 5, 2011

Michinori Suginome and co-workers at Kyoto University have published in JACS on the enantiospecificity of a Suzuki-Miyaura reaction and they show that inversion or retention can occur depending on the additive.

Suzuki-Miyaura

JACS paper

Posted in Asymmetric, cross coupling, Methodology, Palladium, Suzuki-Miyaura, Transition Metal, Zirconium | Leave a Comment »

Pyrrole access

Posted by naturalproductman on June 5, 2011

Manojit Pal and co-workers from the University of Hyderabad have reported in Chem Comm on a multi-component reaction to make substituted pyrroles.

MCC

Chem Comm paper

Posted in Cascade Reactions, cross coupling, Methodology, Multi-Component Coupling, Palladium, Suzuki-Miyaura, Transition Metal | Leave a Comment »

Haouamine B Progress

Posted by naturalproductman on January 20, 2011

Yoshiki Morimoto and co-workers from Osaka City University have published in Chemical Communications on their progress towards haouamine B.  Phil Baran and co-worker have published on a synthesis of haouamine A – however, haouamine B, which differs from the A form by a hydroxy group in one of the aryl rings (the one fused to the five membered ring), is less stable than A and has not been synthesized yet.

houamine

Chem Comm paper

Posted in Alkaloids, cross coupling, Methodology, Palladium, Suzuki-Miyaura, Transition Metal | Leave a Comment »

Didemnaketal Synthesis

Posted by naturalproductman on October 29, 2010

Haruhiko Fuwa and co-workers from Tohoku University have published in Organic Letters on a synthesis of didemnaketal which has an IC50 value of 1 micromolar against HIV-1 protease.  The spiroketal unit was accessed from a PPTS catalyzed condensation of an alcohol and a dihydropyran.

spiroketal

 

OL paper

Posted in Cascade Reactions, cross coupling, Diseases, HIV, Methodology, Palladium, Polyketides, Spiroketals, Suzuki-Miyaura, Transition Metal | Leave a Comment »

Suzuki-Miyaura with Aryltriazenes

Posted by naturalproductman on July 13, 2010

Meiming Luo and co-workers from Sichuan University have published in the Beilstein Journal of Organic Chemistry on a Suzuki-Miyaura reaction that involves the use of a triazene compound, which couples with an arylboronic acid.

Suzuki


Beilstein JOC paper

Posted in cross coupling, Methodology, Palladium, Suzuki-Miyaura, Transition Metal | Leave a Comment »

Indene Synthesis

Posted by naturalproductman on May 20, 2010

Mark Lautens and co-worker at the University of Toronto have published in Organic Letters on the use of a gem-dibromoalkene to form an indene ring and a new C-C bond via an intermolecular Suzuki/Heck reaction.  Usually we see alkynes as precursors to these transition metal catalyzed indene formations, but this dibromo-olefin is another approach.

dibromo

OL paper

Posted in cross coupling, Methodology, Mizoroki-Heck, Palladium, Ring forming, Suzuki-Miyaura, Transition Metal | Leave a Comment »

Boron Enolate from Alkyne

Posted by naturalproductman on April 9, 2010

Tom Sheppard and co-workers from the University College in London have recently reported in JACS on an unconventional way to form boron enolates from alkynes – it basically looks like the addition of the -OH group accross the alkyne for a 6-endo-dig cyclization.

boron enolate

JACS paper

OL paper

Posted in Chan Lam, Copper, cross coupling, Gold, Methodology, Named Reactions, Suzuki-Miyaura, Transition Metal | Leave a Comment »

Regioselective Suzuki-Miyaura

Posted by naturalproductman on March 31, 2010

Peter Langer and co-workers at the Universitat Rostock have recently published in Synlett on a regioselective Suzuki-Miyaura reaction that selectively couples a boronic acid to a specific triflate on an aryl ring.  Their explanation had to do with the electronics.

regioselective

Synlett paper

Posted in cross coupling, Methodology, Palladium, Suzuki-Miyaura, Transition Metal | Leave a Comment »

Tandem Oxidation-Wittig

Posted by naturalproductman on February 17, 2010

Richard Taylor and co-workers at the University of York have recently published in Synlett on a tandem approach to synthesize dibromo-beta-substituted enone from an alpha hydroxy ketone.   Hydrazine was condensed with the carbonyl and a Suzuki-Miyaura cross coupling followed to form a pyrazole ring.

tandem

Synlett paper

Posted in Cascade Reactions, cross coupling, Methodology, Named Reactions, Palladium, Steroids, Suzuki-Miyaura, Transition Metal, Wittig | Leave a Comment »

A Palladium Cascade

Posted by naturalproductman on January 21, 2010

Antonio Mourino and co-workers at the Universidad de Santiago de Compostela y Unidad Asociada al CSIC in Spain have recently published in Chemistry – A European Journal on a cascade reaction catalyzed by palladium – the reaction involves a cyclization of an alkynyl enol triflate followed by a Suzuki-Miyaura coupling with the vinyl palladium intermediate.

cascade

Chemistry – A European Journal paper

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

 
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