Regioselective Rh-Catalyzed Hydroformylation of 1,1,3-Trisubstituted Allenes Using BisDiazaPhos Ligand

Eshon, Josephine; Landis, Clark R.; Schomaker, Jennifer M.

doi:10.1021/acs.joc.7b01140

Cited by 7 publications

(3 citation statements)

References 32 publications

(76 reference statements)

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Using BisDiazaphos ligand, the reaction was performed regioselectively on the terminal carbon of the allene under 10 bar of CO/H 2 (1:1). 197 Carbon dioxide was also used as an electrophile with palladium catalysts. Thus, Iwasawa published the hydrocarboxylation on the more substituted carbon of 1,2disubstituted terminal allenes with a silyl pincer-type palladium complex (Scheme 90).…”

Section: Umpoled Reaction With Carbon Dioxide and Carbon Monoxide (An...mentioning

confidence: 99%

See 1 more Smart Citation

Metal-Catalyzed Intermolecular Hydrofunctionalization of Allenes: Easy Access to Allylic Structures via the Selective Formation of C–N, C–C, and C–O Bonds

2020

View full text Add to dashboard Cite

show abstract

Section: Umpoled Reaction With Carbon Dioxide and Carbon Monoxide (An...mentioning

confidence: 99%

“…The rhodium-catalyzed hydroformylation was also extended to 1,1,3-trisubstituted allenes by Schomaker and co-workers in 2017. Using BisDiazaphos ligand, the reaction was performed regioselectively on the terminal carbon of the allene under 10 bar of CO/H 2 (1:1) …”

Section: C–c Bond Formationmentioning

confidence: 99%

Metal-Catalyzed Intermolecular Hydrofunctionalization of Allenes: Easy Access to Allylic Structures via the Selective Formation of C–N, C–C, and C–O Bonds

2020

View full text Add to dashboard Cite

show abstract

“…Meanwhile considerable progress has also been documented in the hydroformylation of alkynes [75] and allenes [76].…”

Section: Fig 27 N-regioselective Hydroformylation Of Propene and Important Subsequent Transformationsmentioning

confidence: 99%

Hydroformylation

2021

View full text Add to dashboard Cite

Hydroformylation is one of the most important homogeneously catalyzed reactions on an industrial scale. The manufacture of bulk chemicals clearly dominates. Large cobalt- and rhodium-based processes are mature technologies that have been developed over the past 80 years. Meanwhile, the potential of hydroformylation for the production of fine chemicals (perfumes, pharmaceuticals) has also been recognized. This review gives insight into the state-of-the-art of the reaction and its development. It commences with some remarks on the accidental discovery by the German chemist Otto Roelen within the historical and personal framework of the Fischer–Tropsch process, followed by the mechanistic basics of the catalytic cycle, metals used for the catalyst as well as their organic ligands. In addition, the stability of ligands and catalysts is addressed. The huge potential of this transformation is demonstrated using a variety of substrates. Finally, the use of some surrogates for syngas is discussed.

show abstract

Cationic Rhodium(I)‐Catalyzed Asymmetric Cyclohydroformylation of 1,6‐Enynes with Formaldehyde

Hayashi

Akiyama

Kakiuchi

et al. 2023

Chemistry An Asian Journal

View full text Add to dashboard Cite

We report a rhodium(I)-catalyzed asymmetric cyclohydroformylation reaction of 1,6-enynes with formaldehyde. The reaction of 1,6-enynes with formaldehyde in the presence of a cationic Rh(I) catalyst, such as [Rh(cod) 2 ] + OTf À , and a chiral biaryl diphosphine led to asymmetric cyclohydroformylation to produce aldehydes with higher-order structures highly enantioselectively. This transformation procedure is applicable to a variety of enynes, with wide compatibility in various atoms liking between the alkyne and alkene parts, substituents at the alkyne terminus, and substituents at the alkene part, being converted to newly formed aldehydes in 14% to 90% yields with 50% to 98% ee. The products were further transformed with various nucleophiles to alcohols, an amine, and a diene without loss of chirality at their γ-position.

show abstract

Regioselective Rh-Catalyzed Hydroformylation of 1,1,3-Trisubstituted Allenes Using BisDiazaPhos Ligand

Cited by 7 publications

References 32 publications

Metal-Catalyzed Intermolecular Hydrofunctionalization of Allenes: Easy Access to Allylic Structures via the Selective Formation of C–N, C–C, and C–O Bonds

Metal-Catalyzed Intermolecular Hydrofunctionalization of Allenes: Easy Access to Allylic Structures via the Selective Formation of C–N, C–C, and C–O Bonds

Hydroformylation

Cationic Rhodium(I)‐Catalyzed Asymmetric Cyclohydroformylation of 1,6‐Enynes with Formaldehyde

Contact Info

Product

Resources

About