Recent advances in application of intramolecular Suzuki cross-coupling in cyclization and heterocyclization

Abstract

Palladium-catalyzed reactions are key steps for the formation of carbon-carbon bonds in modern synthetic chemistry and among these reactions few have influenced organic synthesis as greatly as the Suzuki-Miyaura reaction which was first reported in 1979. This review highlights recent and major developments of this approach in intramolecular cyclization and heterocyclization reactions.

Synthesis and Evaluation of Novel Analogues of Ripostatins

“…The extended carboxylic acid fragment was appended to the acetal 16 by Mitsunobu esterification [9] and the resulted ester was then introduced into hydroboration/Suzuki cross-coupling [10] reaction conditions to give the macrolactone 18 , in moderate yield (Scheme 3). We also isolated some quantities of alcohol 19 following oxidative workup of the reaction.…”

Total synthesis of natural products containing benzofuran rings

“…The key features for their synthesis are bromination, Suzuki coupling reaction, 323 and an oxidation/oxa-Michael reaction. 324 The concise total synthesis of (AE)-anastatins A and B were accomplished in eight steps starting from the market purchasable phloroglucinol with acceptable overall yield of 9% and 10%, respectively.…”

Synthesis of palladated magnetic nanoparticle (Pd@Fe3O4/AMOCAA) as an efficient and heterogeneous catalyst for promoting Suzuki and Sonogashira cross‐coupling reactions

“…The growing tendency to Suzuk reaction is mostly due to the use of available, easy to handle and safe starting materials . Formation of C‐C bonds from this reaction is frequently the key‐step of most total syntheses of natural products which led to awarding the Chemistry Nobel Prize to its discoverer, Prof. Akira Suzuki, in 2010, of course shared with Richard Heck and Ichi Negishi …”

“…The growing tendency to Suzuk reaction is mostly due to the use of available, easy to handle and safe starting materials. [14] Formation of C-C bonds from this reaction is frequently the key-step of most total syntheses of natural products [15,16] which led to awarding the Chemistry Nobel Prize to its discoverer, Prof. Akira Suzuki, in 2010, of course shared with Richard Heck and Ichi Negishi. [17] Suzuki reaction results in the formation of the bi-aryl compounds which are often employed as appropriate ligands and also are the key intermediates for the manufacture of various drugs such as antiplatelet, antidiuretic, anti-inflammatory, antiviral (Figure 1.).…”