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Creators/Authors contains: "Szostak, Michal"

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  7. The Sonogashira cross-coupling is one of the most fundamental C–C bond-forming reactions, wherein the strategic value of an alkyne moiety has found widespread applications at the frontiers of organic chemistry, materials science and drug discovery as the cornerstone building block of chemical synthesis. Although traditional variants of Sonogashira cross-coupling involve aryl halides and pseudohalides as electrophiles, recently, tremendous advances have been made in the unconventional disconnection exploiting common carboxylic acids by a decarbonylation/transmetalation pathway. This manifold (1) permits one to take advantage of carboxylic acids as a ubiquitous class of substrates in organic synthesis that are derived from an orthogonalmore »pool of precursors to aryl halides and pseudohalides and (2) combines the benefits of the palladium-catalyzed C(sp 2 )–C(sp) coupling of terminal alkynes with the inherent presence of the carboxylic acid moiety in pharmaceuticals, natural products and organic materials. In this highlight article, we summarize the recent progress in the decarbonylative Sonogashira cross-coupling of carboxylic acid electrophiles to produce arylalkynes and conjugated enynes as a novel avenue for chemical synthesis, whereby a large number of chemical reactions critically rely on transformations of alkynes.« less
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  10. Piperazine ranks as the third most common nitrogen heterocycle in drug discovery, and it is the key component of several blockbuster drugs, such as Imatinib (also marketed as Gleevec) or Sildenafil, sold as Viagra. Despite its wide use in medicinal chemistry, the structural diversity of piperazines is limited, with about 80% of piperazine-containing drugs containing substituents only at the nitrogen positions. Recently, major advances have been made in the C–H functionalization of the carbon atoms of the piperazine ring. Herein, we present an overview of the recent synthetic methods to afford functionalized piperazines with a focus on C–H functionalization.
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