141362-07-4Relevant academic research and scientific papers
Benzo/Naphtho-Anellated Dihydro-1,2-oxaphosphinines and Ring-Opening to P-Tertiary 2-Phosphanyl-1,1′-biaryl-2-ol Derivatives – Syntheses and Structures
Wawrzyniak, Piotr,Kindermann, Markus K.,Thede, Gabriele,Schulzke, Carola,Jones, Peter G.,Heinicke, Joachim W.
, p. 3580 - 3586 (2017)
Reaction of naphthylphenol 1a and phenylnaphthol 1b, respectively, with PCl3 in the presence of ZnCl2 gave mixed benzo- and naphtho-anellated 6-chloro-6H-1,2-oxaphosphinines 2a and 2b. Treatment with equimolar amounts of tBuLi led to
Nickel-Catalyzed Cross-Coupling of Organolithium Reagents with (Hetero)Aryl Electrophiles
Heijnen, Dorus,Gualtierotti, Jean-Baptiste,Hornillos, Valentín,Feringa, Ben L.
, p. 3991 - 3995 (2016/03/16)
Nickel-catalyzed selective cross-coupling of aromatic electrophiles (bromides, chlorides, fluorides and methyl ethers) with organolithium reagents is presented. The use of a commercially available nickel N-heterocyclic carbene (NHC) complex allows the reaction with a variety of (hetero)aryllithium compounds, including those prepared via metal-halogen exchange or direct metallation, whereas a commercially available electron-rich nickel-bisphosphine complex smoothly converts alkyllithium species into the corresponding coupled product. These reactions proceed rapidly (1 h) under mild conditions (room temperature) while avoiding the undesired formation of reduced or homocoupled products. Nickel-catalyzed cross-coupling of aromatic electrophiles with organolithium reagents is presented. The use of a commercially available nickel N-heterocyclic carbene complex allows reaction with a variety of (hetero)aryllithium compounds, whereas a commercially available electron-rich nickel bisphosphine complex smoothly converts alkyllithium species into the corresponding coupled product.
Catalytic direct cross-coupling of organolithium compounds with aryl chlorides
Hornillos, Valentin,Giannerini, Massimo,Vila, Carlos,Fananas-Mastral, Martin,Feringa, Ben L.
supporting information, p. 5114 - 5117 (2013/10/22)
Palladium-catalyzed direct cross-coupling of aryl chlorides with a wide range of (hetero)aryl lithium compounds is reported. The use of Pd-PEPPSI-IPent or Pd2(dba)3/XPhos as the catalyst allows for the preparation of biaryl and heterobiaryl compounds in high yields under mild conditions (room temperature to 40 C) with short reaction times.
Microwave-promoted Suzuki-Miyaura coupling of arylboronic acids with 1-bromo-2-naphthol, o-bromophenol, and o-chlorophenol
Wawrzyniak, Piotr,Heinicke, Joachim
, p. 8921 - 8924 (2007/10/03)
In this letter we report a simple and efficient way for the direct Suzuki-Miyaura cross-coupling of unprotected 2-hydroxyaryl bromides and of 2-chlorophenol with arylboronic acids using suitable phosphine/Pd(OAc)2 catalysts systems with moist K3PO4/toluene or moist CsF/dioxane and microwave heating (20 min 105 °C to 3 h 100-120 °C) with an internal temperature control providing 2-hydroxybiaryls in yields up to 98%.
A Palladium-Catalyzed Intramolecular Arene-Triflate Coupling for the Synthesis of Fluoranthrenes and Benzofluoranthrenes
Rice, Joseph E.,Cai, Zhen-Wei
, p. 1663 - 1678 (2007/10/02)
A method for the preparation of fluoranthrenes and benzofluoranthrenes from aryl bromides and aryl methoxymethyl ethers is described.The key step in this synthesis is an intramolecular triflate-arene coupling mediated by bis(triphenylphosphine)palladium(II)chloride.Fluoranthrene, benzofluoranthrene, benzofluoranthrene, and indenopyrene were prepared in yields of 84-91percent.The regiospecific synthesis of substituted benzofluoranthrenes was demonstrated by the preparation of 6-fluorobenzofluoranthrene (72percent yield) and 5- and 6-methoxybenzofluoranthrene in yields of 73percent and 62percent respectively when the reaction was conducted in the presence of excess triphenylphosphine.Key Words: synthesis; palladium; triflate; fluoranthrene; benzofluoranthrene
