Hetaryl Halides Research Articles

ChemInform Abstract: Nickel‐Catalyzed Cross‐Electrophile Coupling with Organic Reductants in Non‐Amide Solvents.

AbstractA high‐yielding cross‐electrophile coupling of aryl or hetaryl halides with functionalized alkyl halides is examined.

Phosphine-Free Suzuki Cross-Coupling Reaction Using an Efficient and Reusable Pd Catalyst in an Aqueous Medium Under Microwave Irradiation

We report here an improved, highly efficient, and general method for the ligand-free Suzuki cross-coupling reaction to the synthesis of biaryls, bipyridyls, thienylpyridine, and allylphenols. Microwave irradiation of (het)aryl halides and (hetaryl, allyl)arylboronic acid N-methyl-iminodiacetic acid (MIDA) ester, using polyurea microencapsulated palladium catalyst (Pd EnCat 30), gave the coupling adducts 1a–x in excellent yields in just 10–18 min.

ChemInform Abstract: Highly Selective Palladium‐Catalyzed Cross‐Coupling of Secondary Alkylzinc Reagents with Heteroaryl Halides.

AbstractA general Pd‐based catalytic system is developed to allow the cross‐coupling of a broad spectrum of hetaryl halides with secondary Grignard reagents.

ChemInform Abstract: Palladium‐Catalyzed Completely Linear‐Selective Negishi Cross‐Coupling of Allylzinc Halides with Aryl and Vinyl Electrophiles.

AbstractEfficient Negishi cross‐coupling reactions of prenylated and related β,γ‐unsaturated zinc bromides with aryl or hetaryl halides as well as vinyl triflates are developed using a Pd‐precatalyst containing the CPhos ligand.

ChemInform Abstract: A Copper‐Free, Cross‐Coupling of Terminal Alkynes with Hetaryl Halides.

AbstractAn inexpensive Pd‐catalyzed cross‐coupling reaction of haloarenes (I) with terminal alkynes is developed to yield the expected internal alkynes (III).

ChemInform Abstract: A Recyclable Cu‐Catalyzed C—N Coupling Reaction in Water and Its Application to Synthesis of Imidazo[1,2‐a]quinoxaline.

AbstractThe polystyrene supported pyrrole‐2‐carbohydrazide ligand is synthesized and can be successfully used for Cu‐catalyzed Ullmann‐type reactions of aryl and hetaryl halides with primary amines and imidazole.

A copper-free, cross-coupling of terminal alkynes with hetaryl halides

Substituted ethynyl heterocycles and heteroarylbutenynes are synthesized efficiently in good yields via a copper-free, cross-coupling reaction.

Convenient Synthesis of Benzoxazolone Derivatives by Cross-Coupling of Benzoxazolone Boronates with Aryl Halides

Benzoxazolone derivatives with various substituents at the C-5 position were synthesized efficiently via benzoxazolone boronates as the key intermediate. The target compounds were also synthesized from (het)aryl halides in a one-pot process. These methods permitted efficient exploratory syntheses of a series of benzoxazolone derivatives.

Nanosized Pd(0)-arabinogalactan composites as catalysts in the Sonogashira reaction

Zero-valent palladium nanoparticles stabilized by arabinogalactan polysaccharide matrix were successfully used for the first time as phosphine-free catalyst in the cross-coupling of terminal alkynes with aryl and hetaryl halides.

ChemInform Abstract: Novel Diversely Substituted 1‐Heteroaryl‐2‐imidazolines for Fragment‐Based Drug Discovery.

AbstractThe synthesis of the title compounds (V) (20 examples) is based on a Pd‐catalyzed Buchwald—Hartwig N‐heteroarylation of 2‐imidazolines with hetaryl halides.

First example of the $$ C_{sp^2 } $$ -P bond formation in the reaction of red phosphorus with hetaryl halides

Direct reactions of red and white phosphorus with electrophiles (aryland hetarylalkenes, arylacetylenes, alkyl, allyl, and benzyl halides) in superbasic systems alkali metal hydroxide – dipolar aprotic solvent (DMSO, HMPTA) or under the conditions of phase transfer catalysis are now considered as a novel chlorine-free method of formation of the С–P bond [1, 2]. Within this approach, the one-pot methods have been elaborated for the synthesis of various phosphines, phosphine oxides, and phospinic acids [1, 2] which had earlier been obtained by multistep processes from phosphorus halides. However, in the case of the substitution reaction only the Сsp3–P bond was formed. Recently, tris(1-naphthyl)phosphine was synthesized from red phosphorus and 1-naphthyl bromide in the system KОН–DMSO [3]. To the best of our knowledge, there are no data in the literature on the formation of the Сsp2–P in the reactions of elemental phosphorus with hetaryl halides in superbasic systems.

ChemInform Abstract: A Mild and Efficient Synthesis of Aryl Sulfones from Aryl Chlorides and Sulfinic Acid Salts Using Microwave Heating.

AbstractA CuCl‐catalyzed reaction of aryl and hetaryl halides with sulfinic acid salts is developed to yield a variety of sulfones (III) (41 examples).

ChemInform Abstract: Palladium‐Catalyzed Decarboxylative Coupling of Potassium Nitrophenyl Acetates with Aryl Halides.

AbstractA wide range of aryl and hetaryl halides is successfully converted to 1,1‐diarylmethane structures.

ChemInform Abstract: Synthesis and Suzuki—Miyaura Cross‐Coupling Reactions of Potassium Boc‐Protected Aminomethyltrifluoroborate with Aryl and Hetaryl Halides.

AbstractThe reaction of various chlorides with borate (II) in the presence of either SPhos (Ia) or XPhos (Ib) affords synthetically important aminomethyl units.

Synthesis and Suzuki-Miyaura cross-coupling reactions of potassium Boc-protected aminomethyltrifluoroborate with aryl and hetaryl halides.

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

ChemInform Abstract: A General and Highly Efficient Method for the Construction of Aryl‐Substituted N‐Heteroarenes.

AbstractA highly efficient method for the cross coupling of various hetaryl halides with arylboronic acids is presented.

ChemInform Abstract: Palladium‐Catalyzed Alkynylation of Aryl and Hetaryl Halides: A Journey from Conventional Palladium Complexes or Salts to Palladium/Carbon

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

Palladium-Catalyzed Alkynylation of Aryl and Hetaryl Halides: A Journey from Conventional Palladium Complexes or Salts to Palladium/Carbon

Palladium-catalyzed alkynylation of aryl and hetaryl -halideshas found wide application in the areas of synthetic, heterocyclic,and medicinal chemistry. Attempts to introduce the stable and potentiallyrecyclable palladium/carbon has provided an attractivealternative to the homogeneous palladium catalytic process. Thepresent article provides a personal account of the outcome of theuse of conventional palladium catalysts versus palladium/carbon,especially under Sonogashira conditions. 1 Introduction 1.1 The Focus on Palladium/Carbon 1.2 The Origin of the Research 2 Copper-Free Sonogashira Coupling: An Unusual Observation 3 Palladium-Mediated Synthesis of 3-Substituted (Thio)flavones:The Role of ( S)-Prolinol and Copper 4 Palladium/Carbon in Water 4.1 Synthesis of Benzo[ B]furans 4.2 2-Aminoethanol as an Alternative Base: Synthesis of Aryl- andHetaryl-Substituted Alkynes 4.3 Synthesis of Indoles 5 Palladium/Carbon in Organic Solvents 5.1 Synthesis of Isocoumarins and Phthalides 5.2 Synthesis of Thieno[2,3- C]pyranones 5.3 Synthesis of Alkynylpyrimidines 5.4 Synthesis of Furoquinolines and Pyrroloquinolines 5.5 Synthesis of 2 H-1,2-Benzothiazine1,1-Dioxides 6 Alkynylation of b-Chloroacroleins 7 Synthesis of Substituted Benzenes Fused with Carbocycles/Heterocycles:Palladium Salts versus Palladium/Carbon 8 Palladium/Carbon in the Union of Organic Azide andTerminal Alkynes 9 Conclusions: Towards Fulfilling the Requirements for Commercialization

Hydroarylation of bicyclic, unsaturated dicarboximides: access to aryl-substituted, bridged perhydroisoindoles

The C–C coupling of the two bicyclic, unsaturated dicarboximides 6 and 8 with aryl and hetaryl halides gave under reductive Heck conditions the 5-substituted N-phenylbicyclo[2.2.1]heptane-2,3-dicarboximides 7 and 9. Reduction of these imides opens a new access to the bridged perhydroisoindole derivatives 12 and 14 with prospective biological activity.

Direct Aminoalkylation via Nickel-Catalyzed Negishi Cross-Coupling Reactions

A new general method for the one-pot introduction of aminoalkyl groups via Negishi-type cross-coupling is reported. It was applied to the cross-coupling with both aryl and hetaryl halides and triflates furnishing the respective products with good to excellent yields. It is noteworthy that cross-coupling of tropanyl zinc reagents proceeds with 100% exo-selectivity. This is due to the stereospecific formation of the corresponding Grignard reagent.