Direct aziridination of alkenes by a cationic (Salen)ruthenium(VI) nitrido complex

Wai-Lun Man; William W. Y. Lam; Shek-Man Yiu; Tai-Chu Lau; Shie-Ming Peng

doi:10.1021/ja045845f

Direct aziridination of alkenes by a cationic (Salen)ruthenium(VI) nitrido complex

Wai-Lun Man
, William W. Y. Lam
, Shek-Man Yiu
, Tai-Chu Lau
, Shie-Ming Peng

Research output: Journal Publications and Reviews › RGC 21 - Publication in refereed journal › peer-review

95 Citations (Scopus)

Abstract

[Ru^VI(N)(salchda)(CH₃OH)]PF₆ (1) (salchda = N,N′-bis(salicylidene)o-cyclohexyldiamine dianion) reacts readily with 2,3-dimethyl-2-butene at room temperature in the presence of pyridine or 1-methylimidazole to give initially [Ru^VI(Az¹ _(-H))(salchda)(py)]PF₆ (2, Az¹ = 2,2,3,3-tetramethylaziridine), which is then slowly reduced to [Ru^III(Az¹)(salchda)(py)]PF₆ (3). 1 also reacts with a variety of aryl-substituted alkenes such as styrene and trans-β-methylstyrene in the presence of py or 1-MeIm to give the corresponding ruthenium(III) aziridine complexes. The structures of 3 and [Ru^III(Az²)(salchda)(1-MeIm)]PF₆ (4, Az² = trans-2-methyl-3-phenylaziridine) have been determined by X-ray crystallography. The Ru-N(aziridine) distances (2.1049, 2.097 Å) are consistent with a neutral aziridine ligand. The C-C and C-N distances in the aziridine ligands are all indicative of single bonds. Copyright © 2004 American Chemical Society.

Original language	English
Pages (from-to)	15336-15337
Journal	Journal of the American Chemical Society
Volume	126
Issue number	47
DOIs	https://doi.org/10.1021/ja045845f
Publication status	Published - 1 Dec 2004

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@article{e93d63ca53df456e96fee07c5949fbdd,

title = "Direct aziridination of alkenes by a cationic (Salen)ruthenium(VI) nitrido complex",

abstract = "[RuVI(N)(salchda)(CH3OH)]PF6 (1) (salchda = N,N′-bis(salicylidene)o-cyclohexyldiamine dianion) reacts readily with 2,3-dimethyl-2-butene at room temperature in the presence of pyridine or 1-methylimidazole to give initially [RuVI(Az1 (-H))(salchda)(py)]PF6 (2, Az1 = 2,2,3,3-tetramethylaziridine), which is then slowly reduced to [RuIII(Az1)(salchda)(py)]PF6 (3). 1 also reacts with a variety of aryl-substituted alkenes such as styrene and trans-β-methylstyrene in the presence of py or 1-MeIm to give the corresponding ruthenium(III) aziridine complexes. The structures of 3 and [RuIII(Az2)(salchda)(1-MeIm)]PF6 (4, Az2 = trans-2-methyl-3-phenylaziridine) have been determined by X-ray crystallography. The Ru-N(aziridine) distances (2.1049, 2.097 {\AA}) are consistent with a neutral aziridine ligand. The C-C and C-N distances in the aziridine ligands are all indicative of single bonds. Copyright {\textcopyright} 2004 American Chemical Society.",

author = "Wai-Lun Man and Lam, \{William W. Y.\} and Shek-Man Yiu and Tai-Chu Lau and Shie-Ming Peng",

year = "2004",

month = dec,

day = "1",

doi = "10.1021/ja045845f",

language = "English",

volume = "126",

pages = "15336--15337",

journal = "Journal of the American Chemical Society",

issn = "0002-7863",

publisher = "American Chemical Society",

number = "47",

}

TY - JOUR

T1 - Direct aziridination of alkenes by a cationic (Salen)ruthenium(VI) nitrido complex

AU - Man, Wai-Lun

AU - Lam, William W. Y.

AU - Yiu, Shek-Man

AU - Lau, Tai-Chu

AU - Peng, Shie-Ming

PY - 2004/12/1

Y1 - 2004/12/1

N2 - [RuVI(N)(salchda)(CH3OH)]PF6 (1) (salchda = N,N′-bis(salicylidene)o-cyclohexyldiamine dianion) reacts readily with 2,3-dimethyl-2-butene at room temperature in the presence of pyridine or 1-methylimidazole to give initially [RuVI(Az1 (-H))(salchda)(py)]PF6 (2, Az1 = 2,2,3,3-tetramethylaziridine), which is then slowly reduced to [RuIII(Az1)(salchda)(py)]PF6 (3). 1 also reacts with a variety of aryl-substituted alkenes such as styrene and trans-β-methylstyrene in the presence of py or 1-MeIm to give the corresponding ruthenium(III) aziridine complexes. The structures of 3 and [RuIII(Az2)(salchda)(1-MeIm)]PF6 (4, Az2 = trans-2-methyl-3-phenylaziridine) have been determined by X-ray crystallography. The Ru-N(aziridine) distances (2.1049, 2.097 Å) are consistent with a neutral aziridine ligand. The C-C and C-N distances in the aziridine ligands are all indicative of single bonds. Copyright © 2004 American Chemical Society.

AB - [RuVI(N)(salchda)(CH3OH)]PF6 (1) (salchda = N,N′-bis(salicylidene)o-cyclohexyldiamine dianion) reacts readily with 2,3-dimethyl-2-butene at room temperature in the presence of pyridine or 1-methylimidazole to give initially [RuVI(Az1 (-H))(salchda)(py)]PF6 (2, Az1 = 2,2,3,3-tetramethylaziridine), which is then slowly reduced to [RuIII(Az1)(salchda)(py)]PF6 (3). 1 also reacts with a variety of aryl-substituted alkenes such as styrene and trans-β-methylstyrene in the presence of py or 1-MeIm to give the corresponding ruthenium(III) aziridine complexes. The structures of 3 and [RuIII(Az2)(salchda)(1-MeIm)]PF6 (4, Az2 = trans-2-methyl-3-phenylaziridine) have been determined by X-ray crystallography. The Ru-N(aziridine) distances (2.1049, 2.097 Å) are consistent with a neutral aziridine ligand. The C-C and C-N distances in the aziridine ligands are all indicative of single bonds. Copyright © 2004 American Chemical Society.

UR - https://www.scopus.com/pages/publications/9644262312

UR - https://www.scopus.com/record/pubmetrics.uri?eid=2-s2.0-9644262312&origin=recordpage

U2 - 10.1021/ja045845f

DO - 10.1021/ja045845f

M3 - RGC 21 - Publication in refereed journal

SN - 0002-7863

VL - 126

SP - 15336

EP - 15337

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

IS - 47

ER -

Direct aziridination of alkenes by a cationic (Salen)ruthenium(VI) nitrido complex

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