Search results for "oxidative coupling"

Oxidative Coupling Reactions of 1,3-Diarylpropene Derivatives to Dibenzo[a,c]cycloheptenes by PIFA

2011

The oxidative cyclization reactions of a variety of α-benzyl-cinnamates can be selectively performed with hypervalent iodine as an oxidant. The dibenzo[a,c]cycloheptenes were isolated in up to 55 % yield. When an oxo substrate is applied, the yield was significantly increased. With this synthetic approach, a central intermediate for the synthesis of metasequirin-B was obtained in three steps from very simple starting materials. For this transformation, both aryl moieties have to be activated.

Cover Picture: Oxidative Cyclization Reaction of 2-Aryl-Substituted Cinnamates To Form Phenanthrene Carboxylates by Using MoCl5 (Chem. Eur. J. 39/201…

2014

ChemInform Abstract: Oxidative Transformation of Aryls Using Molybdenum Pentachloride

2012

Molybdenum pentachloride combines a strong Lewis acid character with an unusually high oxidation potential creating a powerful reagent for oxidative transformations. Since the oxidative coupling reaction of aryls is induced at an extraordinarily high reaction rate, a variety of labile groups, e.g. iodo, tert-alkyl, etc., are tolerated on the aromatic core. Furthermore, the co-formed molybdenum salts can either be exploited for template effects to obtain uncommon geometries in a preferred manner, or redox-play starts after aqueous workup. Therefore MoCl5 represents a unique and easily available reagent.

Silver ion oxidative coupling of diene and triene-diolates of unsaturated carboxylic acids. A facile synthesis of octa- and dodeca-dienedioic acids

1988

Abstract Polyunsaterated dicarboxylic acids 3 and 5 are very easily prepared by oxidative coupling of lithium diene- and triene-diolates 1 and 2 with silver nitrate.

Synthesis of Dienedioic and Tetraenedioic Acids by Oxidative Coupling of Unsaturated Carboxylic Acid Dienediolates by 1,2-Diiodoethane

1993

Abstract Acyclic and cyclic unsaturated carboxylic acids 1 to 4 are most easily converted to unsaturated dicarboxylic acids 5 to 8 by oxidative coupling of their diene- or triene-diolates by 1,2-diiodoethane. This procedure improves formerly reported oxidations by iodine or silver salts.

ChemInform Abstract: Synthesis of Dienedioic and Tetraenedioic Acids by Oxidative Coupling of Unsaturated Carboxylic Acid Dienediolates by 1,2-Diiodo…

2010

Abstract Acyclic and cyclic unsaturated carboxylic acids 1 to 4 are most easily converted to unsaturated dicarboxylic acids 5 to 8 by oxidative coupling of their diene- or triene-diolates by 1,2-diiodoethane. This procedure improves formerly reported oxidations by iodine or silver salts.

Catalytic Functionalization of Methane and Light Alkanes in Supercritical Carbon Dioxide

2014

International audience; The development of catalytic methods for the effective functionalization of methane yet remains a challenge. The best system known to date is the so-called Catalytica Process based on the use of platinum catalysts to convert methane into methyl bisulfate with a TOF rate of 10−3 s. In this contribution, we report a series of silver complexes containing perfluorinated tris(indazolyl)borate ligands that catalyze the functionalization of methane into ethyl propionate upon reaction with ethyl diazoacetate (EDA) by using supercritical carbon dioxide (scCO2) as the reaction medium. The employment of this reaction medium has also allowed the functionalization of ethane, prop…

Unique regioselectivity in the C(sp3)-H α-alkylation of amines: the benzoxazole moiety as a removable directing group.

2014

The benzoxazol-2-yl- substituent was found to act as a removable activating and directing group in the Ir-catalyzed alkylation of C(sp(3))-H bonds adjacent to nitrogen in secondary amines. It can be easily introduced by oxidative coupling or by an SNAr reaction, and it can be removed by hydroxide or by hydride reduction. For 1,2,3,4-tetrahydroisoquinolines, activation exclusively takes place in the 3-position. A variety of activated as well as unactivated terminal olefins are suitable reaction partners.

A Regio- and Diastereoselective Anodic Aryl-Aryl Coupling in the Biomimetic Total Synthesis of (-)-Thebaine.

2018

The biosynthesis of thebaine is based on the regioselective, intramolecular, oxidative coupling of (R)-reticuline. For decades, chemists have sought to mimic this coupling by using stoichiometric oxidants. However, all approaches to date have suffered from low yields or the formation of undesired regioisomers. Electrochemistry would represent a sustainable alternative in this respect but all attempts to accomplish an electrochemical synthesis of thebaine have failed so far. Herein, a regio- and diastereoselective anodic coupling of 3',4',5'-trioxygenated laudanosine derivatives is presented, which finally enables electrochemical access to (-)-thebaine.

MoVReagents in Organic Synthesis

2016

The use of MoV reagents, and in particular MoCl5, in organic synthesis is surveyed. The oxidative treatment of aromatic substrates is the most common application. The unique properties of these reagents are due to their high oxidative power combined with exquisite Lewis acid properties. In several examples MoV reagents outperform other common oxidative coupling reagents. C–C bond formation through inter- and intramolecular oxidative coupling can lead to selective formation of five- to eight-membered ring systems. Mechanistic investigations of the courses of reactions involving MoV reagents and aromatic substrates indicate that radical cations are initially formed, entering the oxidative cou…