Stable bis(silyl)nickel complexes with o-carboranyl unit: a facile double silylation of alkynes and alkenes

Kang, Yoon Jung; Kang, Sang Ook; Ko, Jaejung; Lee, Jung-Hyun; Kong, Young Kun

doi:10.1039/a806457a

Cited by 43 publications

(16 citation statements)

References 10 publications

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“…The NiSi bonds in 1 measure 2.285 and 2.304 Å. We are not aware of any comparable Ni 0 complex with ligands containing silicon donor atoms, but the observed bond lengths agree well with those observed for silyl or silylene complexes of Ni II , Ni III , or even Ni IV : [{ o ‐(SiMe 2 ) 2 C 2 B 10 H 10 }Ni(PEt 3 ) 2 ] 2.242 Å,25 [{1,2‐C 6 H 4 (SiH)(SiH 2 )} 2 Ni 2 (Me 2 PCH 2 CH 2 PMe 2 ) 2 ] 2.210–2.304 Å,26 [{1,2‐C 6 H 4 (SiH 2 )} 2 Ni(Me 2 PCH 2 CH 2 PMe 2 )] 2.252 and 2.290 Å 27…”

supporting

confidence: 67%

The Organocatalytic Vinylogous Aldol Reaction: Recent Advances

Pansare

Paul

2011

Chemistry A European J

164

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Over the past decade, organocatalysis has emerged as a powerful tool for stereoselective carbon-carbon bond formation under exceptionally mild conditions. The organocatalytic versions of a large number of traditional synthetic transformations are now well established and the quest for new applications of the basic concepts of organocatalysis continues. This review addresses the emergent interest in the organocatalytic vinylogous aldol reaction. While noteworthy progress has been made in this area, significant challenges lie ahead.

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confidence: 67%

The Organocatalytic Vinylogous Aldol Reaction: Recent Advances

Pansare

Paul

2011

Chemistry A European J

164

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“…[21] Eine der größten Hürden für die Entwicklung einer Lö-sungschemie mit Silicium-Clusterionen ist die geringe Lös-lichkeit der M I 12 Si 17 -Phasen. Bisher ist das einzige geeignete Lösungsmittel flüssiger Ammoniak, [17][18][19] [25] [{1,2-C 6 H 4 (SiH 2 )-(SiH)} 2 Ni 2 (Me 2 PCH 2 CH 2 PMe 2 ) 2 ] 2.210-2.304 , [26] [{1,2-C 6 H 4 (SiH 2 )} 2 Ni(Me 2 PCH 2 CH 2 PMe 2 )] 2.252 und 2.290 . [27] Erste quantenchemische Berechnungen des zentralen…”

Section: àunclassified

“…Uns ist kein vergleichbarer Ni 0 -Komplex mit Liganden bekannt, die Silicium-Donoratome enthalten. Die beobachteten Bindungslängen stimmen jedoch gut mit denen für Silyl-oder Silylen-Komplexe von Ni II , Ni III oder sogar Ni IV überein: [{o-(SiMe 2 ) 2 C 2 B 10 H 10 }Ni(PEt 3 ) 2 ] 2.242 , [25] [{1,2-C 6 H 4 (SiH 2 )-(SiH)} 2 Ni 2 (Me 2 PCH 2 CH 2 PMe 2 ) 2 ] 2.210-2.304 , [26] [{1,2-C 6 H 4 (SiH 2 )} 2 Ni(Me 2 PCH 2 CH 2 PMe 2 )] 2.252 und 2.290 . [27] Erste quantenchemische Berechnungen des zentralen [{Ni(CO) 2 } 2 (m-Si 9 ) 2 ] 8À -Komplexes auf Hartree-Fock-Niveau [28] lassen erkennen, dass die Bindungssituation der Ni-Si-Bindung jeder anderen Ni-Koordination durch Atome der dritten Periode sehr ähnlich ist; die p-Rückbindung ist auch hier sehr schwach.…”

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Chemie mit substituentenfreien Silicium‐Clustern in Lösung – ein Übergangsmetallkomplex eines Polysilicid‐Anions

et al. 2009

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“…A nickel(II)-carborane complex 4.10, prepared by the reaction of o-bis(dimethylsilyl)carborane (4.9) and Ni(PEt 3 ) 4 catalyzes the disilylation of alkynes with 4.9 (Scheme 4.9) [29]. The reaction is accompanied by evolution of 1 equiv.…”

Section: Bis-silylation and Bis-germylationmentioning

confidence: 99%

Reaction of Alkynes

Ikeda

2005

Modern Organonickel Chemistry

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Since the earliest investigations represented by cycloaddition [1] and carboxylation [2], the nickel-catalyzed reactions of alkynes have been extensively studied by many research groups. This chapter highlights recent developments in the nickelcatalyzed reactions of alkynes. Recent advancements in cycloaddition and the carboxylation of alkynes are described in Chapters 6 and 7, respectively.The most extensively studied reaction is the addition reaction of an AaB species (e.g., HaH, H-metals, metals-metals, CaH, and C-metals, where metals ¼ Si, Sn, B, etc.) to alkynes (Scheme 4.1). Generally, the addition of an AaB species to alkynes starts with oxidative addition of the AaB species to a nickel(0) complex to generate an AaNiaB species (see Section 1.7.1). The insertion of an alkyne into either the AaNi or the BaNi bond gives the alkenylnickel intermediate(s), which undergo reductive elimination to produce the alkenes functionalized with an A and B functionalities at the 1,2-positions (see Section 1.7.4). The A and B groups are usually introduced on the same face of alkynes, and cis-alkenes with respect to A and B are produced. When an AaB is CaX (X ¼ halogens, O, N), the alkenylnickel X intermediates are capable of undergoing, instead of reductive elimination, Modern Organonickel Chemistry. Edited by Y. Tamaru

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Stable bis(silyl)nickel complexes with o-carboranyl unit: a facile double silylation of alkynes and alkenes

Cited by 43 publications

References 10 publications

The Organocatalytic Vinylogous Aldol Reaction: Recent Advances

The Organocatalytic Vinylogous Aldol Reaction: Recent Advances

Chemie mit substituentenfreien Silicium‐Clustern in Lösung – ein Übergangsmetallkomplex eines Polysilicid‐Anions

Reaction of Alkynes

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