547740-47-6

Upstream product

• 821-41-0 5-Hexen-1-ol 
• 201230-82-2 carbon monoxide 
• 547740-45-4 N-phenylcarbamic acid hex-5-enyl ester 
• 103-71-9 phenyl isocyanate 

Downstream Products

• 1118635-12-3 (E)-9-(phenylcarbamoyloxy)non-2-enoic acid 
• 1227007-39-7 (E)-9-(phenylcarbamoyloxy)non-3-enoic acid 

Relevant academic research and scientific papers

Room temperature ambient pressure (RTAP)-hydroformylation in water using a self-assembling ligand

We herein demonstrate a hydroformylation at room temperature and ambient pressure (RTAP) using our Rh/6-DPPon (1) system in aqueous media. The hydrogen bonding network of the ligand backbone stays intact, exemplified by the excellent regioselectivity for the linear aldehyde. Various substrates with different functional groups (with some prone to hydrolysis) are stable under the applied conditions and can undergo hydroformylation resulting in good yields. Copyright

Combined transition-metal- and organocatalysis: An atom economic C3 homologation of alkenes to carbonyl and carboxylic compounds

A combination of regioselective room-temperature/ambient-pressure hydroformylation (transitionmetal catalysis) and decarboxylative Knoevenagel reactions (organocatalysis) allowed for the development of an efficient, one-pot C3 homologation of terminal alkenes to (E)-α,β-unsaturated acids and esters, (E)-β,γ-unsaturated acids, (E)-α-cyano acrylic acids, and α,β-unsaturated nitriles. All reactions proceed under mild conditions, tolerate a variety of functional groups, and furnish unsaturated carbonyl compounds in good yields and with excellent regioand stereocontrol. Further, an iterative C2 homologation of (E)-α,β-unsaturated carboxylic acids is possible through a combination of decarboxylative hydroformylation employing a supramolecular catalyst followed by decarboxylative Knoevenagel condensation with an organocatalyst.

Practical synthesis of (E)-α,β-unsaturated carboxylic acids using a one-pot hydroformylation/decarboxylative Knoevenagel reaction sequence

Combining the regioselective room temperature/ambient pressure hydroformylation and a modification of the Doebner-Knoevenagel reaction allowed for the development of an efficient, one-pot procedure for the synthesis of (E)-α,β-unsaturated carboxylic acids. The reaction proceeds under mild conditions, tolerates a variety of functional groups and gives (E)-α,β-unsaturated carboxylic acids in good yields and with excellent regio-and stereocontrol. The practicability of this process has been demonstrated by a short protecting group-free synthesis of the queen honeybee pheromones 9-ODA[( E)-9-oxodec-2-enoic acid] and 9-HDA[( E)-9-hydroxydec-2-enoic acid].

Bidentate ligands by self-assembly through hydrogen bonding: A general room temperature/ambient pressure regioselective hydroformylation of terminal alkenes

The 6-DPPon (1)/rhodium catalyst allows for the first time a room temperature/ambient pressure regioselective hydroformylation of terminal alkenes with low catalyst loadings in good activity. The generality of this catalyst under these conditions was demonstrated for a wide range of structurally diverse alkenes equipped with many important functional groups. Thus, this practical and highly selective hydroformylation protocol, which omits the need for special pressure equipment, should find wide application in organic synthesis.

Hydroformylation

The present invention relates to a process for hydroformylating in the presence of a catalyst comprising at least one complex of a metal of transition group VIII with mono-phosphorus compounds which are capable of dimerizing via noncovalent bonds as ligands, to such catalysts and to their use.

Hydrogen bonding as a construction element for bidentate donor ligands in homogeneous catalysis: Regioselective hydroformylation of terminal alkenes

A new concept for the construction of bidentate ligands for homogeneous metal complex catalysis is described. The concept relies on the self-assembly of monodentate ligands through hydrogen bonding. As a prototype of such systems, 6-diphenylphosphanyl-2-pyridone (6-DPPon) was shown to form a chelate in the coordination sphere of a transition metal center through unusual pyridone/hydroxypyridine hydrogen bonding (X-ray). This hydrogen bonding stays intact in a catalytic reaction as proven upon highly regioselective hydroformylation of terminal alkenes. Regioselectivities and reactivities observed rank the 6-DPPon/rhodium system among the most active and regioselective catalysts for n-selective hydroformylation of terminal alkenes. Copyright