144880-16-0

Upstream product

• 821-41-0 5-Hexen-1-ol 
• 201230-82-2 carbon monoxide 
• 124-38-9 carbon dioxide 

Downstream Products

• 170798-95-5 ethyl 4-methyl-8-(p-toluenesulfonyloxy)octanoate 
• 137305-44-3 (E)-5-Methyl-6-oxo-8-phenylsulfanyl-oct-7-enal 
• 137305-54-5 methyl (+/-)-(3aR*,4S*,5S*,7aS*)-3a,4,5,6,7,7a-hexahydro-7a-methyl-7-oxo-5-phenylthioindane-4-carboxylate 
• 137305-50-1 methyl (+/-)-(3aR*,4S*,5S*,7aS*)-7-(tert-butyldimethylsiloxy)-3a,4,5,7a-tetrahydro-7a-methyl-5-phenylthioindane-4-carboxylate 
• 137305-53-4 methyl (2Z,9Z)-7-methyl-8-oxo-10-(phenylthio)deca-2,9-dienoate 
• 137305-46-5 methyl (2E,9Z)-7-methyl-8-oxo-10-(phenylthio)deca-2,9-dienoate 
• 137305-52-3 methyl (2Z,9E)-7-methyl-8-oxo-10-(phenylthio)deca-2,9-dienoate 
• 137305-45-4 methyl (2E,9E)-7-methyl-8-oxo-10-(phenylthio)deca-2,9-dienoate 
• 144880-24-0 (E)-8-(4-Methoxy-phenylsulfanyl)-5-methyl-6-oxo-oct-7-enal 
• 144880-48-8 methyl (E,E)-7-methyl-8-oxo-10-phenylsulfinyldeca-2,9-dienoate 
• 137305-54-5 methyl (+/-)-(3aR*,4S*,5R*,7aR*)-3a,4,5,6,7,7a-hexahydro-7a-methyl-7-oxo-5-phenylthioindane-4-carboxylate 
• 144880-28-4 methyl (2E,9Z)-10-(4-methoxyphenylthio)-7-methyl-8-oxodeca-2,9-dienoate 
• 144880-26-2 methyl (2E,9E)-10-(4-methoxyphenylthio)-7-methyl-8-oxodeca-2,9-dienoate 
• 144880-36-4 methyl (+/-)-(3aR*,4S*,5S*,7aS*)-3a,4,5,6,7,7a-hexahydro-5-(4-methoxyphenylthio)-7a-methyl-7-oxoindane-4-carboxylate 

Relevant academic research and scientific papers

Chemo- And regioselective hydroformylation of alkenes with CO2/H2over a bifunctional catalyst

As is well known, CO2 is an attractive renewable C1 resource and H2 is a cheap and clean reductant. Combining CO2 and H2 to prepare building blocks for high-value-added products is an attractive yet challenging topic in green chemistry. A general and selective rhodium-catalyzed hydroformylation of alkenes using CO2/H2 as a syngas surrogate is described here. With this protocol, the desired aldehydes can be obtained in up to 97% yield with 93/7 regioselectivity under mild reaction conditions (25 bar and 80 °C). The key to success is the use of a bifunctional Rh/PTA catalyst (PTA: 1,3,5-triaza-7-phosphaadamantane), which facilitates both CO2 hydrogenation and hydroformylation. Notably, monodentate PTA exhibited better activity and regioselectivity than common bidentate ligands, which might be ascribed to its built-in basic site and tris-chelated mode. Mechanistic studies indicate that the transformation proceeds through cascade steps, involving free HCOOH production through CO2 hydrogenation, fast release of CO, and rhodium-catalyzed conventional hydroformylation. Moreover, the unconventional hydroformylation pathway, in which HCOOAc acts as a direct C1 source, has also been proved to be feasible with superior regioselectivity to that of the CO pathway.

Comparison of “on water” and solventless procedures in the rhodium-catalyzed hydroformylation of diolefins, alkynes, and unsaturated alcohols

Catalytic systems containing Rh(acac)(CO)2 or Rh/PAA (PAA?=?polyacrylic acid) and hydrophobic phosphine (PPh3) were used in the hydroformylation of diolefins, alkynes, and unsaturated alcohols under solventless and “on water” conditions. The total yield of dialdehydes obtained from 1,5-hexadiene and 1,7-octadiene reached 99%, and regioselectivity towards linear dialdehydes was higher in the “on water” system. The tandem hydroformylation-hydrogenation of phenylacetylene led to the formation of saturated aldehydes (3-phenylpropanal and 2-phenylpropanal) at 98% conversion with a good regioselectivity towards the linear aldehyde in the “on water” reaction. In contrast, solventless conditions appeared better in the hydroformylation of 1-propen-3-ol. 4-Hydroxybutanal, formed in this reaction with an excellent selectivity, was next transformed to tetrahydrofuran-2-ol via a ring-closure process. Cyclic products were also obtained in hydroformylation of 1-buten-3-ol. In reaction of undec-1-ol and 2-allylphenol linear aldehydes were formed with the yield 69–87%. The hydroformylation of 3-buten-1-ol performed under “on water” conditions showed very good regioselectivity towards a linear aldehyde, 5-hydroxypentanal. Further cyclization of the aldehyde to tetrahydropyran-2-ol was observed.