60112-47-2

Upstream product

• 58824-56-9 1-(p-bromophenyl)prop-2-en-1-ol 
• 60112-46-1 (E)-methyl 4-(4-bromophenyl)-4-hydroxy-but-2-enoate 
• 106-37-6 1.4-dibromobenzene 
• 184360-96-1 (E)-4-(4-bromophenyl)-3-butenoic acid 

Relevant academic research and scientific papers

Guiding a divergent reaction by photochemical control: Bichromatic selective access to levulinates and butenolides

Allylic and acrylic substrates may be efficiently transformed by a sequential bichromatic photochemical process into derivatives of levulinates or butenolides with high selectivity when phenanthrene is used as a regulator. Thus, UV-A photoinduced cross-metathesis (CM) couples the acrylic and allylic counterparts and subsequent UV-C irradiation initiates E-Z isomerization of the carbon-carbon double bond, followed by one of two competing processes; namely, cyclization by transesterification or a 1,5-H shift and tautomerization. Quantum chemical calculations demonstrate that intermediates are strongly blue-shifted for the cyclization while red-shifted for the 1,5-H shift reaction. Hence, delaying the double bond migration by employing UV-C absorbing phenanthrene, results in a selective novel divergent all-photochemical pathway for the synthesis of fundamental structural motifs of ubiquitous natural products.

Lewis base-catalyzed electrophilic lactonization of selenyl bromide resin and facile solid-phase synthesis of furan-2(5H)-one derivatives

A facile solid-phase synthesis approach was developed for the rapid synthesis of multi-substituted furan-2(5H)-one derivatives libraries. The synthetic strategy included the selenyl bromide resin-induced electrophilic lactonization catalyzed by Lewis base, lithiation, nucleophilic substitution and oxidation-elimination of the selenium resins. The advantages of the new method are good yields, high purity, straightforward operations and high diversity of the products, lack of odor, and good stability of the selenium resins. Copyright

Catalytic use of selenium electrophiles in cyclizations

A new and convenient one-pot method for a catalytic addition-elimination reaction using selenium electrophiles has been developed. In the presence of 5 mol % diphenyl diselenide, [bis(trifluoroacetoxy)iodo]benzene in acetonitrile converted a range of (E)-3-butenoic acids into the corresponding butenolides in good yields.