63591-04-8

Upstream product

• 32359-01-6 hexenylmagnesium bromide 
• 582-24-1 1-phenyl-2-hydroxyethanone 
• 17689-03-1 1-hexynyllithium 
• 693-02-7 hex-1-yne 

Downstream Products

• 1221575-73-0 methyl 2-butyl-4-phenylfuran-3-carboxylate 

Relevant academic research and scientific papers

Rh(I)-Catalyzed Decarboxylative Arylation of Alkynyl Cyclic Carbonates: Divergent Access to Substituted α-Allenols and 1,3-Butadienes

Rh(I)-catalyzed decarboxylative arylation of alkynyl cyclic carbonates using commercially available and low-toxic aryl boronic acids has been disclosed. Depending on the nature of the cyclic carbonates, the methodology provides a straightforward platform to access either substituted 2,3-allenols or 1,3-butadiene derivatives. Internal alkynyl cyclic carbonates undergo monoarylation to conveniently afford 2,3-allenols with high syn-selectivity for the aryl and hydroxy groups. Whereas, terminal alkynyl carbonates led to the formation of diarylated 1,3-butadiene derivatives having cis-configuration for the two aryl groups via allenyl rhodium(I)alkoxide intermediate. The compatibility of various functional groups allowed to develop a library of diversely functionalized scaffolds with excellent regioselectivity in good yields. Late-stage transformation of a series of natural products highlights the wide applicability of the arylation process. Additionally, scale-up experiments and downstream transformations of α-allenol derivatives into other valuable heterocycles illustrate the efficacy of the protocol.

Cu-catalyzed synthesis of tetrasubstituted 2,3-allenols through decarboxylative silylation of alkyne-substituted cyclic carbonates

An efficient and mild Cu-catalyzed protocol has been developed for the decarboxylative silylation of alkyne-functionalized cyclic carbonate substrates affording 2,3-allenols featuring four different substituents. This practical methodology gives access to a wide scope of tetrasubstituted functionalized allenes in excellent yields.

Poly(ethylene glycol) as a reaction matrix in platinum- or gold-catalyzed cycloisomerization: A mechanistic investigation

Design for diversity: A new catalytic system based on PEG-3400 and a metal salt (Pt or Au) was designed to efficiently perform a cycloisomerization reaction under microwave irradiation, which gave diverse heterocycles in good to excellent yields, after a

Synthesis of furan-3-carboxylic and 4-methylene-4,5-dihydrofuran-3- carboxylic esters by direct palladium iodide catalyzed oxidative carbonylation of 3-yne-1,2-diol derivatives

A variety of 3-yne-1,2-diol derivatives 1, bearing a primary or secondary alcoholic group at C-1, have been efficiently converted into high value added furan-3-carboxylic esters 2 in one step by PdI2/KI-catalyzed direct oxidative carbonylation, carried out in alcoholic media under relatively mild conditions (100 °C under 40 atm of a 4/1 mixture of CO and air). Carbonylated furans 2 were obtained in fair to excellent isolated yields (56-93%) through a sequential 5-endo-dig heterocyclization-alkoxycarbonylation- dehydration process, using only oxygen as the external oxidant. Under similar conditions, 2-methyl-3-yne-1,2-diols 3, bearing a tertiary alcoholic group, afforded 4-methylene-4,5-dihydrofuran-3-carboxylates 4 in satisfactory yields (58-70%).

A simple and convenient synthesis of substituted furans and pyrroles by CuCl2-catalyzed heterocyclodehydration of 3-yne-1,2-diols and N-Boc- or N-tosyl-1-amino-3-yn-2-ols

A simple and economical synthesis of substituted furans and pyrroles, by ligand-free CuCl2-catalyzed heterocyclodehydration of readily available 3-yne-1,2-diols and N-Boc- or N-tosyl-1-amino-3-yn-2-ols, respectively, is presented. Reactions are carried out in MeOH at 80-100 °C for 1-24 h and afford the corresponding heterocyclic derivatives in 53-99% isolated yields.