147454-73-7

Upstream product

• 88-67-5 2-Iodobenzoic acid 
• 4187-87-5 1-Phenyl-2-propyn-1-ol 
• 2142-68-9 1-(2-chlorophenyl)ethanone 
• 201230-82-2 carbon monoxide 
• 100-52-7 benzaldehyde 

Downstream Products

• 4333-66-8 (Z)-3-(2'-oxo-2'-phenyl)ethylidene isobenzofuran-1(3H)-one 

Relevant academic research and scientific papers

Cyclic enolates of Ni and Pd: Equilibrium between C- and O-bound tautomers and reactivity studies

2-Acylaryl complexes of Ni and Pd containing chelating diphosphines react with KtBuO to give metallacyclic enolate complexes. While coordination through the carbon atom is preferred in the case of Pd, the nickel O-enolate compounds are formed as the corresponding O-tautomers. Slow equilibration between O- and C-enolate tautomers is observed for the nickel complex with an unsubstituted enolate function (M-O-C=CH2). Theoretical DFT calculations suggest that the barrier for the tautomer exchange has its origin in the rigidity of the metallacycle. Whilst the C-enolate tautomer is unreactive towards aldehydes, the corresponding O-enolate adds to MeCHO and PhCHO, giving rise to products that retain the enolate functionality. The carbonylation of these products cleanly leads to the formation of enol lactones in a highly selective manner.

Synthesis and aldol reactivity of O- and C-enolate complexes of nickel

The often facile C-/O-tautomerization of transition metal enolates is severely hindered in the cyclic Ni complexes 1 and 2, allowing the study of their individual reactivities. At room temperature only the O-bound tautomer, 2, reacts with aldehydes, giving rise to the corresponding addition products. Copyright

Palladium-catalysed heteroannulation with terminal alkynes: Synthesis of phthalides

The palladium-copper-catalysed heteroannulation of o-iodobenzoic acid 3 with terminal alkynes 4-18 leads to the synthesis of (Z)-3-alkylidenephthalides 19-33 as the major products. In certain cases, the formation of isocoumarins 34-37 is also observed.