Control of intramolecular acetate–allenylidene coupling by spectator co-ligand π-acidity

Harlow, Karsten J.; Hill, Anthony F.; Welton, Tom

doi:10.1039/a902021g

Cited by 28 publications

(19 citation statements)

References 10 publications

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“…Previous studies have demonstrated that RuHCl(CO)A C H T U N G T R E N N U N G (PPh 3 ) 3 (1) can undergo insertion reactions with alkynes, [27,28] allenes [29] and functionalized olefins such as 2-vinylipyridine, and allylic amines. [30] Insertion reactions of RuHClA C H T U N G T R E N N U N G (PPh 3 ) 3 (3), [31,32] OsHCl(CO)A C H T U N G T R E N N U N G (PPh 3 ) 3 (2) [33,34] and RhH(CO)-A C H T U N G T R E N N U N G (PPh 3 ) 3 (4) [35,36] with alkynes and allenes have also been reported. In view of the reported reactivity toward unsaturated substrates, one might expect that these hydride complexes may undergo reversible insertion reactions with olefins and are potential candi- The H/D exchange reactions of the six-coordinate 18e complexes MHCl(CO)A C H T U N G T R E N N U N G (PPh 3 ) 3 (M = Ru, Os) probably involve dihydrogen (B) or dihydrogen bonded species (A or A') illustrated in [Eq.…”

Section: Selection Of Catalystsmentioning

confidence: 99%

Hydrogen/Deuterium Exchange Reactions of Olefins with Deuterium Oxide Mediated by the Carbonylchlorohydrido‐ tris(triphenylphosphine)ruthenium(II) Complex

Tse¹,

Xue²,

Lin³

et al. 2010

Adv Synth Catal

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Section: Selection Of Catalystsmentioning

confidence: 99%

Hydrogen/Deuterium Exchange Reactions of Olefins with Deuterium Oxide Mediated by the Carbonylchlorohydrido‐ tris(triphenylphosphine)ruthenium(II) Complex

Tse¹,

Xue²,

Lin³

et al. 2010

Adv Synth Catal

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“…It has also been demonstrated that in the presence of acetonitrile ( 53 ) a hexacoordinate acetonitrile ruthenium complex 54 can form (Scheme ) …”

Section: Synthesis and Investigation Of η1‐ And η3‐allyl Ruthenium Mementioning

confidence: 99%

Ruthenium‐Catalyzed Metathesis of Conjugated Polyenes

et al. 2016

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Abstract:In the past decade numerous examples of olefin metathesis-based chemical technologies have been developed making olefin metathesis increasingly dominant in several sustainable and green chemical processes. In spite of the wide application profile, conjugated olefin metathesis -especially conjugated polyene metathesis -is an area of great interest with little exploration. Metathesis of conjugated polyenes is often cumbersome and requires high catalyst loading, most probably due to formation of less or inactive ruthenium  3 -vinylcarbene intermediates. Mechanistic understanding and development of a new highly active catalytic system for olefin metathesis will open new areas for exploration. For example, the utilization of petrochemical by products such as cyclopentadiene or a new way in utilizing butadiene, isoprene and conjugated electron systems containing natural products such as terpenes and polyunsaturated fatty acids. Understanding the mechanism of ruthenium  1 - 3 -vinylcarbene interconversion may open the way to the development of new generation ruthenium-based latent metathesis catalyst systems. This review summarizes the most relevant pioneer work focused on metathesis of conjugated polyenes in order to open new ideas for the development of forthcoming latent metathesis catalysts and to explore different application areas.

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“…The bond lengths RuϪC* ϭ 1.937 (13) Table 1). The most remarkable feature of the structure is the (E) configuration of the alkenyl group which exhibits an RuϪC(1) bond length of 2.030 (12) Å that can be compared with the reported values in other alkenylruthenium(II) complexes with the two CO 2 Me groups in a mutually cis configuration, e.g. 2.07(1) Å and 2.096(7) Å in the complexes [Ru{(E)-C(CO 2 Me)ϭ CH(CO 2 Me)}(η 5 -C 5 H 5 )(dppm)] [18] and [Ru{(E)-C(CO 2 Me)ϭCH(CO 2 Me)}(η 5 -Ph 4 C 4 COH)(CO) 2 ], [19] respectively.…”

Section: Full Papermentioning

confidence: 99%

“…More recently, this procedure has also been used as an alternative synthetic route for Grubbs catalyst B (Scheme 1). [12] Since access to these precursors {by reactions of the hydride complex [RuH(η 5 -C 9 H 7 )(dppm)] with propargyl alcohols} is limited to the presence of the small bite chelate ligand dppm in the hydride precursor, we believed it would be of interest to investigate the applicability of this synthetic methodology using an analogous chelate ligand.…”

Section: Introductionmentioning

confidence: 99%

(Alkenylalkylidene)(indenyl)ruthenium(II) Complexes: Synthesis by Protonation of Alkenyl Derivatives

Bieger

Dı́ez

Gamasa

et al. 2002

Eur. J. Inorg. Chem.

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The alkenyl complexes [Ru{(E)‐C(CO2Me)=C(H)R}(η5‐C9H7){κ2‐P,P‐(S)‐peap}] [R = CO2Me (3), H (4)], [Ru{(E)‐CH=C(H)Ph}(η5‐C9H7){κ2‐P,P‐(S)‐peap}] (5) have been prepared by reaction of the hydride complex [RuH(η5‐C9H7){κ2‐P,P‐(S)‐peap}] (2) [(S)‐peap = (−)‐(S)‐N,N‐bis(diphenylphosphanyl)(1‐phenylethyl)amine] with an equimolar amount of dimethyl acetylenedicarboxylate, or with an excess of the terminal alkynes methyl propiolate or phenylacetylene. Similarly, vinylalkenyl complexes 6a−d have been synthesized by the regio‐ and stereoselective reaction of the hydride complex 2 with 1‐ethynylcycloalkynols. Protonation of the vinylalkenyl moiety of complexes 6a,c,d with HBF4·OEt2 in diethyl ether afforded the cationic alkenylalkylidene complexes 7a−c. The structures of complexes [RuH(η5‐C9H7){κ2‐P,P‐(S)‐peap}] (2) and [Ru{(E)‐C(CO2Me)=CH(CO2Me)}(η5‐C9H7){κ2‐P,P‐(S)‐peap}] (3) have been determined by X‐ray diffraction methods. The catalytic activity of (alkenylalkylidene)(indenyl)ruthenium(II) complexes 7a−c, 8 and 9 in the ring‐closing metathesis (RCM) of diethyl diallylmalonate has been examined. (© Wiley‐VCH Verlag GmbH, 69451 Weinheim, Germany, 2002)

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Control of intramolecular acetate–allenylidene coupling by spectator co-ligand π-acidity

Cited by 28 publications

References 10 publications

Hydrogen/Deuterium Exchange Reactions of Olefins with Deuterium Oxide Mediated by the Carbonylchlorohydrido‐ tris(triphenylphosphine)ruthenium(II) Complex

Hydrogen/Deuterium Exchange Reactions of Olefins with Deuterium Oxide Mediated by the Carbonylchlorohydrido‐ tris(triphenylphosphine)ruthenium(II) Complex

Ruthenium‐Catalyzed Metathesis of Conjugated Polyenes

(Alkenylalkylidene)(indenyl)ruthenium(II) Complexes: Synthesis by Protonation of Alkenyl Derivatives

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