866558-08-9

Upstream product

• 930-68-7 cyclohexenone 
• 33948-36-6 2-iodocyclohex-2-en-1-one 
• 768-60-5 4-methoxyphenylacetylen 

Downstream Products

• 1234889-26-9 C₁₇H₁₉IO₄ 
• 19234-04-9 2-(p-methoxyphenyl)-benzo[b]furan 

Relevant academic research and scientific papers

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.

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

Highly substituted lactone/ester-containing furan library by the palladium-catalyzed carbonylation of hydroxyl-substituted 3-iodofurans

Highly substituted lactone- and ester-containing furans have been prepared by the efficient palladium-catalyzed intramolecular cyclocarbonylation or intermolecular carboalkoxylation, respectively, of hydroxyl-containing 3-iodofurans, readily prepared by t

Enantioselective synthesis of highly substituted furans by a copper(II)-catalyzed cycloisomerization-indole addition reaction

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

A convenient synthetic route to furan esters and lactones by palladium-catalyzed carboalkoxylation or cyclocarbonylation of hydroxyl-substituted 3-iodofurans

An effective palladium-catalyzed protocol for the intermolecular carboalkoxylation or intramolecular cyclocarbonylation of hydroxyl-substituted 3-iodofurans under carbon monoxide pressure has been developed. The 3-iodofurans are readily prepared by iodocy

Synthesis of highly substituted furans by the electrophile-induced coupling of 2-(1-alkynyl)-2-alken-1-ones and nucleophiles

The coupling of 2-(1-alkynyl)-2-alken-1-ones with nucleophiles, either catalyzed by AuCl3 or induced by an electrophile, provides highly substituted furans in good to excellent yields under very mild reaction conditions. Various nucleophiles, i