771477-46-4

Upstream product

• 33948-36-6 2-iodocyclohex-2-en-1-one 
• 536-74-3 phenylacetylene 
• 930-68-7 cyclohexenone 
• 93338-81-9 2-(phenylethynyl)cyclohex-2-en-1-ol 
• 50870-61-6 2-bromocyclohex-2-en-1-one 

Downstream Products

• 24534-42-7 4-methoxy-2-phenylbenzofuran 
• 771477-53-3 4-methoxy-2-phenyl-4,5,6,7-tetrahydrobenzofuran 
• 866558-05-6 3-iodo-4-methoxy-2-phenyl-4,5,6,7-tetrahydrobenzofuran 
• 917087-34-4 1-(phenylethynyl)bicyclo[4.1.0]heptan-2-one 
• 1188491-48-6 3-allyl-4-(but-3-enyloxy)-4,5,6,7-tetrahydro-2-phenylbenzofuran 
• 1215082-59-9 C₂₀H₁₆O 
• 1221288-92-1 1,3-dibenzyl-5,6,7,7a-tetrahydrobenzo[c]isoxazol-4(1H)-one 

Relevant academic research and scientific papers

Dinucleophilic Reactivity of Isocyanoacetate: Base-Catalyzed One-Pot Access to 4-Azafluorenes and 4-Azafluorenones

A base-catalyzed double annulation of isocyanoacetates with various enynones has been developed for the expeditious synthesis of 4-azafluorene and 4-azafluorenone derivatives. Against the well-known 1,3-dipolar reactivities, the active methylene and isocy

Silver-Free Au(I) Catalysis Enabled by Bifunctional Urea- and Squaramide-Phosphine Ligands via H-Bonding

A library of gold(I) chloride complexes with phosphine ligands incorporating pendant (thio)urea and squaramide H-bond donors was prepared with the aim of promoting chloride abstraction from Au(I) via H-bonding. In the absence of silver additives, complexes bearing squaramides and trifluoromethylated aromatic ureas displayed good catalytic activity in the cyclization of N-propargyl benzamides, as well as in a 1,6-enyne cycloisomerization, a tandem cyclization-indole addition reaction and the hydrohydrazination of phenylacetylene. Kinetic studies and DFT calculations indicate that the energetic span of the reaction is accounted by both the chloride abstraction step, facilitated by the bidentate H-bond donor via an associative mechanism, and the subsequent cyclization step.

Synthesis of bicyclic vinyl triazenes by Ficini-type reactions

Cyclic olefins with triazene functions can display interesting reactivity, but synthetic access to these compounds is limited thus far. Herein, we describe the synthesis of cyclobutenyl triazenes fused to cyclopentanone or cyclohexanone rings. The bicycli

Tethered Counterion-Directed Catalysis: Merging the Chiral Ion-Pairing and Bifunctional Ligand Strategies in Enantioselective Gold(I) Catalysis

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.

Rapid assembly of 3-azidomethylfurans from 2-(1-alkynyl)-2-alken-1-ones enabled by silver catalysis

A rapid access to useful 3-azidomethylfurans is developed via Ag(I)-catalyzed cascade annulation/azidation of 2-(1-alkynyl)-2-alken-1-ones. The salient features of the protocol include mild reaction conditions, high efficiency, broad substrate scope, and

Synthesis of Polyheterocyclic Tropones by [2 + 2 + 2 + 1] Carbonylative Cycloaddition of Triynes

A direct synthesis of tropones (2,4,6-cycloheptatrienes) from simple preorganized triynes has been elaborated. This simple rhodium-catalyzed domino strategy allows one-pot access to fully substituted tropones in a 6-6-7-5 tetracyclic core in average to hi

Synthesis of Functionalized Ring C of Escobarines

A synthetic strategy was developed for the preparation of α-ethynyl-α,β-epoxy-β-formyl- and α-ethynyl-α,β-epoxy-β-(hydroxymethyl)cyclohexanone from cyclohexenone as a model study in a proposed synthesis of escobarines. This highly functionalized ring is f

Gold-Catalyzed Concomitant [3 + 3] Cycloaddition/Cascade Heterocyclization of Enynones/Enynals with Azides Leading to Furanotriazines

[Au]-catalyzed [3 + 3] cycloaddition reaction of enynones/enynals with azides, which allows the efficient regioselective synthesis of highly fused furo[3,4-d][1,2,3]triazines in good-to-excellent yields under mild conditions, has been developed. The synth

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

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

Solution-phase synthesis of a highly substituted furan library

A library of furans has been synthesized by iodocyclization and further diversified by palladium-catalyzed coupling processes. The key intermediate 3-iodofurans have been prepared by the electrophilic iodocyclization of 2-iodo-2-alken-1-ones in the presen