Selective Hydroformylation of Internal Acetylenes by PdCl2(PCy3)2:  Remarkable Synergistic Effect of Cobalt1

Ishii, Youichi; Miyashita, Kazuyoshi; Kamita, Kenji; Hidai, Masanobu

doi:10.1021/ja9703887

Cited by 85 publications

(37 citation statements)

References 19 publications

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“…Only a few studies have been performed recently. [41] Most catalysts suffer from low selectivity and/or low yield of the unsaturated aldehydes, mainly because the formation of the corresponding saturated aldehydes. The hydroformylation of symmetrical alkynes is rather simpler; Buchwald and coworkers reported an effective catalyst composed of [Rh(acac)(CO) 2 ] and a diphosphite ligand (26), which worked under mild conditions (Scheme 9).…”

Section: Hydroformylationmentioning

confidence: 99%

Catalytic Markovnikov and anti‐Markovnikov Functionalization of Alkenes and Alkynes: Recent Developments and Trends

et al. 2004

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The regioselective functionalization of terminal alkenes and alkynes is of utmost importance for the synthesis of a wide variety of organic products. Based on the original observation by Vladimir Markovnikov-the pioneer of this field of research-in the 19th century, the possible regioisomeric products are classified as Markovnikov or anti-Markovnikov products. Contrary to traditional belief, it is nowadays possible to control the regiochemistry of various additions of nucleophiles to alkenes and alkynes by applying different transition-metal catalysts. Recent developments in this area of selective functionalization of alkenes and alkynes are reviewed.

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Section: Hydroformylationmentioning

confidence: 99%

Catalytic Markovnikov and anti‐Markovnikov Functionalization of Alkenes and Alkynes: Recent Developments and Trends

et al. 2004

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“…Furthermore, a bimetallic catalyst of PdCl 2 (PCy 3 ) 2 and Co 2 (CO) 8 showed remarkably high catalytic activity. Reaction of 4-octyne under CO and H 2 pressure (35 atm each) at 150 • C in the presence of Et 3 N produced the 2-n-propyl-2-hexenal (2) in 95 % yield [1]. Co 2 (CO) 8 alone is inactive.…”

Section: Carbonylationmentioning

confidence: 99%

Pd(0)‐ and Pd(II)‐Catalyzed Reactions of Alkynes and Benzynes

Tsuji

2004

Palladium Reagents and Catalysts

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“…The design of multidentate ligands containing mixed‐donor atoms to functionalize transition metal centers is a subject of growing interest in coordination and organometallic chemistry Multidentate mixed‐donor ligands function cooperatively in stabilizing metal centers due to their different binding abilities and bridging effect between two or more metal centers . These synergistic effects are helpful in making complexes containing multidentate mixed‐donor ligands very attractive for several applications including catalysis . Catalytic activity of these ligands also results from easy dissociation of the weakly coordinated donor atoms to create vacant site for the incoming substrate.…”

Section: Introductionmentioning

confidence: 99%

Multidentate Pyridyl‐Aminophosphinite and Pyridyl‐Phosphoramidite Ruthenium(II) Complexes: Synthesis, Structure and Application as Levulinic Acid Hydrogenation Pre‐Catalysts

et al. 2019

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Novel multidentate pyridyl‐aminophosphinite (L1) and pyridyl‐phosphoramidite (L2) ligands of N^P^P^N‐donor system have been synthesized via a series of simple steps. The ligands are symmetrical and as a result, their reactions with [Ru(p‐cymene)Cl2]2 and [Ru(benzene)Cl2]2 lead to the formation of four monodentate bimetallic complexes (1–4) that retain the symmetry of the ligands. Meso and racemic mixtures (rac) of bidentate bimetallic complexes 5–8 were formed from the monodentate complexes through coordination of the pyridine nitrogen atoms to the two metal centers. The isomerism occurs at each metal center, which was evidenced by 31P{1H}, 1H NMR spectroscopy and single‐crystal X‐ray diffraction. The complexes were active towards hydrogenation of levulinic acid (LA) to γ‐valerolactone (GVL) using formic acid as the hydrogen source. The complexes are active at relatively low temperatures and are able to perform the hydrogenation in the absence of any additional solvent apart from the reagents to give high TON of 3 600. The catalysts are recyclable up to the fourth cycle, following which 20 % loss of activity is seen.

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Selective Hydroformylation of Internal Acetylenes by PdCl₂(PCy₃)₂: Remarkable Synergistic Effect of Cobalt¹

Cited by 85 publications

References 19 publications

Catalytic Markovnikov and anti‐Markovnikov Functionalization of Alkenes and Alkynes: Recent Developments and Trends

Catalytic Markovnikov and anti‐Markovnikov Functionalization of Alkenes and Alkynes: Recent Developments and Trends

Pd(0)‐ and Pd(II)‐Catalyzed Reactions of Alkynes and Benzynes

Multidentate Pyridyl‐Aminophosphinite and Pyridyl‐Phosphoramidite Ruthenium(II) Complexes: Synthesis, Structure and Application as Levulinic Acid Hydrogenation Pre‐Catalysts

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