852603-07-7Relevant academic research and scientific papers
Pd-mediated synthesis of substituted benzenes fused with carbocycle/heterocycle
Swamy, Nalivela Kumara,Tatini, Lakshmi Kumar,Babu, J. Moses,Annamalai, Pazhanimuthu,Pal, Manojit
, p. 1035 - 1037 (2007)
A new Pd-catalyzed one-pot multicomponent coupling reaction for the construction of benzene ring fused with carbocycle or heterocycle under a Cu-free condition is described. The Royal Society of Chemistry.
Tethered Counterion-Directed Catalysis: Merging the Chiral Ion-Pairing and Bifunctional Ligand Strategies in Enantioselective Gold(I) Catalysis
Frison, Gilles,Guinchard, Xavier,Marinetti, Angela,Retailleau, Pascal,Smal, Vitalii,Voituriez, Arnaud,Zhang, Zhenhao
, p. 3797 - 3805 (2020/03/10)
Tethering a metal complex to its phosphate counterion via a phosphine ligand enables a new strategy in asymmetric counteranion-directed catalysis (ACDC). A straightforward, scalable synthetic route gives access to the gold(I) complex of a phosphine displaying a chiral phosphoric acid function. The complex generates a catalytically active species with an unprecedented intramolecular relationship between the cationic Au(I) center and the phosphate counterion. The benefits of tethering the two functions of the catalyst are demonstrated here in a tandem cycloisomerization/nucleophilic addition reaction, by attaining high enantioselectivity levels (up to 97% ee) at an unusually low 0.2 mol % catalyst loading. Remarkably, the method is also compatible with a silver-free protocol.
Mechanism of a No-Metal-Added Heterocycloisomerization of Alkynylcyclopropylhydrazones: Synthesis of Cycloheptane-Fused Aminopyrroles Facilitated by Copper Salts at Trace Loadings
Wilkerson-Hill, Sidney M.,Yu, Diana,Painter, Phillip P.,Fisher, Ethan L.,Tantillo, Dean J.,Sarpong, Richmond,Hein, Jason E.
supporting information, p. 10569 - 10577 (2017/08/10)
A mechanistic study of a new heterocycloisomerization reaction that forms annulated aminopyrroles is presented. Density functional theory calculations and kinetic studies suggest the reaction is catalyzed by trace copper salts and that a Z- to E-hydrazone
Chemoselectivity control: Gold(I)-catalyzed synthesis of 6,7-dihydrobenzofuran-4(5H)-ones and benzofurans from 1-(alkynyl)-7- oxabicyclo[4.1.0]heptan-2-ones
Wang, Tao,Shi, Shuai,Vilhelmsen, Mie Hojer,Zhang, Tuo,Rudolph, Matthias,Rominger, Frank,Hashmi, A. Stephen K.
supporting information, p. 12512 - 12516 (2013/09/23)
New and chemoselective gold(I)-catalyzed transformations of 1-(arylethynyl)-7-oxabicyclo[4.1.0]- heptan-2-ones were developed. Two completely different products - 6,7-dihydrobenzofuran-4(5H)-ones and benzofurans - could be obtained from the same starting material. The selectivity is determined by the ligand of the gold catalyst: triphenylphosphine delivers 6,7-dihydrobenzofuran-4(5H)-ones, and 1,3-bis(diisopropylphenyl)imidazol-2- ylidene leads to benzofurans. Eleven examples of each case are provided. The mechanistic suggestions for the pathways to both product types are supported by isotope labeling experiments. Complete chemoselectivity control of gold(I)-catalyzed transformations of 1-(arylethynyl)-7-oxabicyclo[4.1.0]heptan- 2-ones, which can be achieved by changing the ligand of the gold catalyst, allows two different products to be obtained from the same starting material, namely, 6,7-dihydrobenzofuran-4(5H)-ones and benzofurans (see scheme), both of which are potent building blocks for synthetic chemistry. IPr: 1,3-bis(diisopropylphenyl)imidazol-2-ylidene. Copyright
Enantioselective synthesis of highly substituted furans by a copper(II)-catalyzed cycloisomerization-indole addition reaction
Rauniyar, Vivek,Wang, Z. Jane,Burks, Heather E.,Toste, F. Dean
supporting information; experimental part, p. 8486 - 8489 (2011/07/09)
A catalytic enantioselective reaction based on a copper(II) catalyst strictly containing chiral anionic ligands is described. In the present work, copper(II)-phosphate catalyst promotes the intramolecular heterocyclization of 2-(1-alkynyl)-2-alkene-1-ones
α-Arylation and alkynylation of cyclic -iodoenones using palladium-catalyzed cross-coupling reactions with trifluoroborate salts
Gueogjian, Kemilla,Singh, Fateh V.,Pena, Jesus M.,Amaral, Monica F. Z. J.,Stefani, Hélio A.
experimental part, p. 427 - 432 (2010/04/26)
An expeditious synthesis of -aryl- and -alkynylcyclohexenones is described and illustrated by palladium-catalyzed cross-coupling reaction of cyclic -iodoenones with potassium aryltrifluoroborate salts. This procedure offers easy access to -arylated and al
