Abstract Die Verwendung von Alkoholen und ungesättigten Reaktanten zur redoxvermittelten Bildung Nucleophil‐Elektrophil‐Paaren stellt einen breiten, neuartigen Ansatz in der Chemie Carbonyl‐Addition dar. Mit dieser Vorgehensweise lassen sich diskrete Redoxmanipulationen, die oftmals für Erzeugung Carbonyl‐Elektrophilen vormetallierten Kohlenstoff‐zentrierten Nucleophilen benötigt werden, vermeiden. Methode begründet eine neue Klasse enantioselektiven C‐C‐Kupplungen, durch Iridium‐ oder...

This review provides recent advances and insights into photoirradiation reactions of acylsilanes, notably via key nucleophilic siloxycarbene intermediates. Nucleophilic addition, insertion reaction, cyclization are discussed in terms reaction mechanism scope.

All essential functional groups in the natural product (±)-trans-dihydronarciclasine (1) were introduced with correct relative configuration a highly endo-selective Diels–Alder cycloaddition of 3,5-dibromo-2-pyrone styrene dienophile (see scheme). The total synthesis 1 from these starting materials was completed 11 steps and 15.8 % overall yield.

Abstract The iridium‐catalyzed, protecting group‐free synthesis of 4‐hydroxy‐2,6‐ cis ‐ or trans ‐pyrans through successive nucleophilic and electrophilic allylations chiral 1,3‐diols occurs with complete levels catalyst‐directed diastereoselectivity in the absence groups, premetallated reagents, discrete alcohol‐to‐aldehyde redox reactions.

Diverse hydrogen-mediated C–C couplings enable construction of the actin-binding marine polyketide swinholide A in only 15 steps (longest linear sequence), roughly half required two prior total syntheses. The redox-economy, chemo- and stereoselectivity embodied by this new class are shown to evoke a step-change efficiency.

Potassium Boc-protected aminomethyltrifluoroborate, a primary aminomethyl equivalent, was synthesized successfully through "one-pot" process. With this trifluoroborate, Suzuki–Miyaura cross-coupling reactions were investigated with variety of both aryl and hetaryl chlorides in good to excellent yields.

Sulfamates were studied as the electrophilic partners in palladium-catalyzed Suzuki-Miyaura cross-coupling reaction with potassium Boc-protected primary and secondary aminomethyltrifluoroborates. A broad range of substrates was successfully coupled to provide desired products. Complex molecules containing a new carbon-carbon bond an aminomethyl moiety could be prepared through this developed method.

Palladium-catalyzed Suzuki–Miyaura cross-coupling reactions were studied with potassium Boc-protected aminomethyltrifluoroborate through C–O activation of various mesylate derivatives to afford the corresponding products in moderate good yields.

Seven potassium Boc-protected secondary aminomethyltrifluoroborates were prepared in a standardized two-step process. The Suzuki–Miyaura cross-coupling reaction was studied with this new class of nucleophiles, and large variety aryl hetaryl chlorides provided the desired products good to excellent yields, thereby allowing easy access aminomethyl substructures.

Enantiomerically enriched potassium β-trifluoroboratoamides were synthesized as air-stable solids in greater than 95:5 dr using pseudoephedrine the chiral auxiliary. With these nucleophiles, Suzuki−Miyaura cross-coupling reactions carried out with various aryl- and hetaryl chlorides good to excellent yields. Moreover, diastereoselectivities preserved throughout reactions.

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3-Hydroxy-2-(trialkylsilyl)phenyl triflates are presented as new versatile hydroxyaryne precursors. These base-activated aryne precursors induced via a C-sp2-to-O 1,3-Brook rearrangement. The reaction of various arynophiles and 3-trialkylsiloxybenzyne generated from 3-hydroxy-2-(trialkylsilyl)phenyl triflate efficiently afforded highly regioselective phenol derivatives. Furthermore, through crossover experiments, the intramolecular mechanism silyl migration was demonstrated.

Tea tree extract, containing antioxidant constituents α-terpineol, terpinen-4-ol, and α-terpinene, has a wide range of applications in the cosmetic, food, pharmaceutical industries. In this study, tea extract showed an anticorrosive effect under 1 M HCl solution on mild steel (MS) 304 stainless (STS). Uniform corrosion for MS pitting STS at 298 K were retarded, with inhibition efficiencies 77% 86%, respectively. The uniform was confirmed by scanning electron microscopy laser confocal terms...

Abstract This short review summarizes the origins and recent progress in 1,4-azaborine research, focusing on synthetic methodologies. Academic laboratories have made significant efforts to generate boron-nitrogen-containing heteroaromatic compounds that mimic arenes. 1,2-, 1,3-, 1,4-Azaborine motifs provided breakthrough molecules applications ranging from medicines materials. Owing advances polyaromatic synthesis industry, research field is currently undergoing a renaissance. Photo-...

Alle wesentlichen funktionellen Gruppen des Naturstoffs (±)-trans-Dihydronarciclasin (1) wurden in einer hoch endo-selektiven Diels-Alder-Cycloaddition zwischen 3,5-Dibrom-2-pyron und einem Styroldienophil mit der richtigen relativen Konfiguration eingeführt (siehe Schema). Die Totalsynthese von 1 aus diesen Ausgangsmaterialien wurde 11 Stufen Gesamtausbeute 15.8 % abgeschlossen.

Using stereo- and site-selective C–H allylation crotylation of unprotected diols, an intermediate in the synthesis premisakinolide A (bistheonellic acid B) that was previously made 16–27 (LLS) steps is now prepared only nine steps. This fragment also represents a C(19)–C(32) actin-binding macrodiolide swinholide A.

An efficient method was developed for the synthesis of unsymmetrical <italic>N</italic>-arylsulfamides using sulfamoyl azides and arylboronic acids in presence 10 mol% copper chloride as catalyst.

Abstract The regioselective ortho arylation of polyhalo‐substituted (hetero)aryl tosylates has been investigated employing an integrated continuous flow/batch protocol. metalation using n ‐BuLi and ZnCl 2 was effectively achieved flow chemistry in a short residence time 10.92 s, without removal the tosyloxy group. Pd‐catalyzed Negishi coupling reactions various iodides with resulting arylzinc species proceeded readily at room temperature 31% to 98% yields. Finally, method applied synthesis...