Journal ArticleDOI
An efficient assembly of heterobenzazepine ring systems utilizing an intramolecular palladium-catalyzed cycloamination.
TLDR
An improved synthesis into the oxazepine and thiazepine ring systems is disclosed, which exploits recent advancements in the palladium-catalyzed amination reaction to form the seven-membered rings.Abstract:
Azaheterocyclic compounds are interesting and medicinally relevant targets. Herein we disclose an improved synthesis into the oxazepine and thiazepine ring systems. The key step in the synthesis exploits recent advancements in the palladium-catalyzed amination reaction, which was utilized to form the seven-membered rings. General conditions for this reaction were Pd2dba3, P(t-Bu)3, NaO-t-Bu alone or with K2CO3, in toluene. The scope of the reaction was investigated, and has been shown to be effective on a variety of substrates as illustrated.read more
Citations
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Journal ArticleDOI
Transition-Metal-Catalyzed Reactions in Heterocyclic Synthesis
Journal ArticleDOI
Palladium‐Catalyzed CN and CO Coupling–A Practical Guide from an Industrial Vantage Point†
Björn Schlummer,Ulrich Scholz +1 more
TL;DR: The palladium-catalyzed coupling of amines with aryl halides or aryls alcohol derivatives, commonly dubbed Buchwald-Hartwig amination, has matured from a synthetic laboratory procedure to a technique that is widely used in natural product synthesis as well as in other fields of academic interest.
Journal ArticleDOI
Efficient nickel-mediated intramolecular amination of aryl chlorides.
TL;DR: The use of an in situ generated Ni(0) catalyst associated with 2,2'-bipyridine or N,N'-bis(2,6-diisopropylphenyl)dihydroimidazol-2-ylidene (SIPr) as a ligand and NaO-t-Bu as the base for the intramolecular coupling of aryl chlorides with amines is described.
Journal ArticleDOI
Synthesis of 2-substituted-benzothiazoles by palladium-catalyzed intramolecular cyclization of o-bromophenylthioureas and o-bromophenylthioamides
TL;DR: In this article, 2-Amino-, and 2-alkyl-benzothiazoles have been efficiently prepared by palladium catalyzed cyclization of o -bromophenylthioureas and o-bromphenylthiamides.
Journal ArticleDOI
9-fluorenylphosphines for the Pd-catalyzed sonogashira, suzuki, and Buchwald-Hartwig coupling reactions in organic solvents and water.
TL;DR: To carry out "green" cross-coupling reactions in water, 9-ethylfluorenyldicyclohexylphosphine was reacted in sulphuric acid to generate the respective 2-sulfonated phosphonium salt.
References
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Journal ArticleDOI
Room-Temperature Palladium-Catalyzed Amination of Aryl Bromides and Chlorides and Extended Scope of Aromatic C−N Bond Formation with a Commercial Ligand
TL;DR: The reactions of aryl bromides with amines occurs at room temperature when using Pd(0) and P(t-Bu)(3) in a 1:1 ratio, and the reactions ofAryl chlorides occur atRoom temperature or 70 degrees C.
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A Highly Active Catalyst for the Room-Temperature Amination and Suzuki Coupling of Aryl Chlorides.
TL;DR: A unique combination of steric and electronic properties appears to determine the effectiveness of phosphanyl-substituted biphenyls as ligands in palladium-catalyzed aminations and Suzuki coupling of aryl chlorides at room temperature.
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Oxygen Production in Nature: A Light-Driven Metalloradical Enzyme Process
Cecilia Tommos,Gerald T. Babcock +1 more
TL;DR: The physical structure and energetics of PSII are reviewed and a metalloradical enzyme mechanism for the water-oxidation process it catalyzes is discussed, which is based on the specifics of the chemistry in which O2 participates.
Journal ArticleDOI
Intramolecular palladium-catalyzed aryl amination and aryl amidation
TL;DR: In this article, aryl halides with pendant amides or sulfonamides are cyclized to form five and six-membered rings, and a similar process can be applied to a ring with pendants.