2018
DOI: 10.1002/cctc.201800713
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Catalyst Pendent‐Base Effects on Cyclization of Alkynyl Amines

Abstract: A family of [CpRu(PP)(MeCN)]PF6 complexes (2 a–e and 4) were prepared in which the bis‐phosphine ligand contains a pendent tertiary amine in the second‐coordination sphere. 2 a–e contain PPh2NR′2 ligands with two amine groups as the pendent base. Complex 4 has the PPh2NPh1 ligand with only one pendent amine. The catalytic performance of 2 a–e and 4 were assessed in the cyclization of 2‐ethynyl aniline and 2‐ethynylbenzyl alcohol. It was revealed that the positioning of the pendent amine near the metal active s… Show more

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Cited by 20 publications
(17 citation statements)
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“…(a) General scheme for the selective intramolecular hydroamination or hydroalkoxylation of alkynes via a Ru vinylidene intermediate. (b) Cooperative catalysts for alkyne hydrofunctionalization based on ruthenium, A and B , and iron, 1a , b (reported in this work).…”
mentioning
confidence: 89%
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“…(a) General scheme for the selective intramolecular hydroamination or hydroalkoxylation of alkynes via a Ru vinylidene intermediate. (b) Cooperative catalysts for alkyne hydrofunctionalization based on ruthenium, A and B , and iron, 1a , b (reported in this work).…”
mentioning
confidence: 89%
“…Ruthenium complexes of the type Ru­(Cp/Cp*)­X­(PR 3 ) 2 (Cp = cyclopentadienyl; Cp* = pentamethylcyclopentadienyl) are active catalysts for intramolecular hydroalkoxylation or hydroamination of alkynes to give O - and N -heterocycles, respectively. Proton transfer steps within the catalytic cycle are promoted by a Brønsted base additive or by a basic site on the phosphine ligands, such as the pyridyl or tertiary amine groups in A and B , respectively (Figure b). These metal–ligand cooperative catalysts operate with faster rates and lower catalysts loadings in comparison to noncooperative analogues .…”
mentioning
confidence: 99%
“…Recently, Blacquiere and co‐workers reported the use of Ru catalysts supported by Cp and macrocyclic amine/phosphine‐mixed ligands (1,5‐ R ’‐3,7‐ R ‐1,5‐diaza‐3,7‐diphosphacyclooctane, P 2 N 2 ) to cyclize amine‐ and alcohol‐tethered alkynes for functionalized isochromenes, indoles and isoquinolinones (Scheme ) . The amine groups on the P 2 N 2 were proposed to serve as proton shuttles in the catalytic cycle.…”
Section: Recent Progress Of Ruthenium‐induced Cyclization Of Alkynesmentioning
confidence: 99%
“… Ru‐catalyzed cycloisomerizations of hydroxyl‐ and amine‐substituted alkynes into isochromenes, indoles and isoquinolinones developed by Blacquiere and co‐workers …”
Section: Recent Progress Of Ruthenium‐induced Cyclization Of Alkynesmentioning
confidence: 99%
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