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Archive for the ‘Sonogashira’ Category

Terreusinone synthesis

Posted by naturalproductman on November 15, 2011

Jonathan Sperry and colleague at the University of Auckland have reported in Organic Letters on a synthesis of terreusinone.

terreusinone

OL paper

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

MCC with Sonogashira

Posted by naturalproductman on September 28, 2011

Matthius Beller and co-workers at Universitat Rostock
Albert-Einstein-Strasse have reported in ACIEE on a palladium catalyzed carbonylative Sonogashira coupling.

palladium

ACIEE paper

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

Deshydroxyajudazol B Synthesis

Posted by naturalproductman on March 16, 2011

Mark Rizzacasa and co-workers at the University of Melbourne have reported in Organic Letters on the synthesis of dehydroxyajudazol B.

total

 

OL paper

Posted in cross coupling, Cycloaddition, Diels-Alder, Methodology, Named Reactions, Oxazoles, Palladium, Pericyclic reactions, Sonogashira, Transition Metal | Leave a Comment »

Sonogashira without Copper

Posted by naturalproductman on September 9, 2010

Hideaki Wakamatsu and co-workers at Tohoku Pharmaceutical University have published in Synlett on a Sonogashira coupling reaction without the use of copper.

sonogashira

Synlett paper

Posted in cross coupling, Methodology, Palladium, Sonogashira, 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 »

Pd-Catalyzed Intermolecular Cyclization Cascade

Posted by naturalproductman on April 26, 2010

Chinmay Chowdhury and co-workers at CSIR have recently reported in Tetrahedron Letters on a tandem cyclization cascade reaction.

cascade

Tetrahedron Letters paper

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

Sonogashira Cascade

Posted by naturalproductman on March 31, 2010

Ali Keivanloo and co-workers from Shahrood University of Technology have recently published in Synthesis on a Sonogashira reaction followed by heteroannulation to form pyrrolo[2,3-b]quinoxaline-
2-carbaldehydes.

sonogashira

Synthesis paper

TL paper

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

Substituted Quinoline Synthesis

Posted by naturalproductman on March 10, 2010

Yuefa Gong and co-workers at Huazhong University of Science and Technology have recently published in Chem Comm on a cascade Sonogashira cyclization process that led to substituted quinolines.

quinoline

Chem Comm paper

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

Iodophenol + Terminal Alkyne = Benzofuran

Posted by naturalproductman on January 21, 2010

Kristin Price and co-workers at Pfizer have recently published in Organic Process Research and Development on a nice Sonogashira coupling of a terminal alkyne with an iodo-phenol compound that subsequently cyclizes to form benzofuran compounds.

benzofurans

OPR&D paper

Posted in Cascade Reactions, Copper, cross coupling, Methodology, Palladium, Ring forming, Sonogashira, Transition Metal | Leave a Comment »

Synthesis of Mersicarpine

Posted by naturalproductman on January 7, 2010

Fukuyama and co-workers at the University of Tokyo have recently reported on a synthesis of mersicarpine.  A highlight of the synthesis includes a coupling between a haloaniline with an alkyne to form the indole moiety.  In addition, the Eschenmoser-Tanabe fragmentation to afford the alkyne fragment was pretty neat.

mersicarpine
JACS paper

Posted in Cascade Reactions, cross coupling, Eschenmoser-Tanabe fragmentation, Methodology, Named Reactions, Sonogashira, Transition Metal | Leave a Comment »

 
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