The Metalation of (tert-Butyldimethylsilyl)(2-pyridylmethyl)amine with Dimethylzinc and Subsequent Zinc-Mediated Carbon−Carbon Coupling Reaction

Westerhausen, Matthias; Bollwein, Tobias; Makropoulos, Nikolaos; Rotter, Thomas; Habereder, Tassilo; Suter, Max; Nöth, Heinrich

doi:10.1002/1099-0682(200103)2001:3<851::aid-ejic851>3.0.co;2-z

Cited by 54 publications

(50 citation statements)

References 16 publications

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“…The alkylzinc amide compounds 210 289 , 211 290 and 212 291 , derived from the corresponding 2-(aminomethyl)pyridines, have structural features identical to those of 203-208 ( Figure 100). They form dimers in which the amide nitrogen atom is µ 2 -bridged between The structure of dimer 218 is remarkable (Figure 101) 78 .…”

Section: T-bu T-bu T-bu T-bu T-bu T-bumentioning

confidence: 98%

Structural Organozinc Chemistry

Jastrzebski¹,

Boersma²,

Koten³

2006

The Chemistry of Organozinc Compounds

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Section: T-bu T-bu T-bu T-bu T-bu T-bumentioning

confidence: 98%

Structural Organozinc Chemistry

Jastrzebski¹,

Boersma²,

Koten³

2006

The Chemistry of Organozinc Compounds

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“…Deswegen setzten wir das leicht zuga È ngliche Bis(methylzink)-1,2-dipyridyl-1,2-bis(tert-butyldimethylsilylamido)ethan (1) [17] zentrale Ethan-Fragment besteht aus den chiralen Kohlenstoffatomen C6 und C7, durch die zentrosymmetrische Raumgruppe liegt aber im Kristall ein Racemat aus (R,R)-und (S,S)-Enantiomeren vor. Weder im Feststoff noch in Lo È sung konnte das (R,S)-Diastereomere beobachtet werden.…”

Section: Ergebnisse Und Diskussionunclassified

“…Die C6±C7-Bindungsla È nge von 157,4(8) pm ist aufgrund intramolekularer sterischer Abstoûungen deutlich aufgeweitet verglichen mit einer C±C-Einfachbindung, allerdings beobachtet man bereits im Edukt 1 einen a È hnlichen Wert von 156,7(4) pm [17]. Aus Abbildung 1 la È ût sich auch die deutlich unterschiedliche chemische Umgebung der beiden an Si1 gebundenen Methylgruppen erkennen; entsprechendes gilt auch fu È r die an Si2 gebundenen Methylreste.…”

Section: Ergebnisse Und Diskussionunclassified

Reaktion von Bis(methylzink)-1,2-dipyridyl-1,2-bis(tert-butyldimethylsilylamido)ethan mit Triisopropylsilylphosphan und -arsan

Westerhausen¹,

Bollwein²,

Warchhold³

et al. 2001

Z. anorg. allg. Chem.

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Frau Professor Marianne Baudler zum 80. Geburtstag gewidmet Inhaltsu È bersicht. Die Umsetzung von Bis(methylzink)-1,2-dipyridyl-1,2-bis(tert-butyldimethylsilylamido)ethan (1) mit Triisopropylsilylphosphan fu È hrt in guten Ausbeuten zu dem dreikernigen Komplex [1,2-Dipyridyl-1,2-bis(tert-butyldimethylsilylamido)ethan]trizink-bis(l-triisopropylsilylphosphandiid) (2). Zwei der Zinkatome weisen die Koordinationszahl von vier auf, wa È hrend das dritte Metallzentrum zwischen den Phosphoratomen mit einem gewinkelten P±Zn±P-Fragment auftritt. Die Reaktion von 1 mit Triisopropylsilylarsan verla È uft analog, allerdings la È ût sich das entstandene [1,2-Dipyridyl-1,2-bis(tert-butyldimethylsilylamido)ethan]trizink-bis(l-triisopropylsilylarsandiid) (3) nicht analysenrein isolieren. Reaction of Bis(methylzinc)-1,2-dipyridyl-1,2-bis(tert-butyldimethylsilylamido)ethane with Triisopropylsilylphosphane and -arsaneAbstract. The reaction of bis(methylzinc)-1,2-dipyridyl-1,2-bis(tert-butyldimethylsilylamido)ethane (1) with triisopropylsilylphosphane gives the three-nuclear complex [1,2-dipyridyl-1,2-bis(tert-butyldimethylsilylamido)ethane]trizincbis(l-triisopropylsilylphosphanediide) (2). Two zinc atoms show the coordination number of four whereas the third metal center is located between the two phosphorus atoms with a bent P±Zn±P-moiety. The reaction of 1 with triisopropylsilylarsane proceeds analoguesly, however, we were not able to isolate analytically pure [1,2-dipyridyl-1,2-bis(tert-butyldimethylsilylamido)ethane]trizinc-bis(l-triisopropylsilylarsanediide) (3).

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“…Protection of the amino functionalities by trialkylsilyl groups led to a quantitative formation of the C-C coupled product [di(methylzinc) 1,2-di(2-pyridyl)-1,2-bis(trialkylsilylamido)ethane] G, as shown in Eq. 2 [19,20]. The protolysis of this zinc complex with acetamide gave 1,2-di(2-pyridyl)-1,2-bis(trialkylsilylamino)ethanes A (R = SiR 3 ) in good yield whereas hydrolysis also cleaved the N-Si bonds [21].…”

Section: Introductionmentioning

confidence: 98%

Synthesis of 1,4-Diamino-2,3-di(2-pyridyl)butane and its Dinuclear Zinc(II) Chloride Complex

Kloubert

Schulz

Görls

et al. 2009

Zeitschrift Für Naturforschung B

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In a Henry-type reaction nitromethane reacts with N-(2-pyridylmethylidene)-methylamine (1) yielding 1-methylamino-1-(2-pyridyl)-2-nitromethane (2) in nearly quantitative yield. This orange compound decomposes slowly in an inert gas atmosphere and fast in contact with air. Therefore 2 has to be stored at −78 • C as a methanol solution. Reduction of 2 with hydrogen in the presence of a Pd/C catalyst leads to the formation of 1,4-dinitro-2,3-di(2-pyridyl)butane (3) in the rather poor yield of 12 %. The major product is the meso-isomer, meso-3, whereas only traces of (R, R)-and (S, S)-isomers of 3 are formed. A conversion of the nitro groups into amino functionalities succeeds with hydrazine hydrate in the presence of a Pd/C catalyst yielding meso-1,4-diamino-2,3-di(2-pyridyl)butane (4). Recrystallization from an aqueous solution gives 4·2H 2 O. The zinc(II) chloride complex 5 with the metal atoms in distorted tetrahedral environments can be isolated after addition of two equivalents of ZnCl 2 to 4. The molecular structures of trimeric 1, meso-3, (R, R)/(S, S)-3, meso-4, and 5 have been determined and are discussed.

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The Metalation of (tert-Butyldimethylsilyl)(2-pyridylmethyl)amine with Dimethylzinc and Subsequent Zinc-Mediated Carbon−Carbon Coupling Reaction

Cited by 54 publications

References 16 publications

Structural Organozinc Chemistry

Structural Organozinc Chemistry

Reaktion von Bis(methylzink)-1,2-dipyridyl-1,2-bis(tert-butyldimethylsilylamido)ethan mit Triisopropylsilylphosphan und -arsan

Synthesis of 1,4-Diamino-2,3-di(2-pyridyl)butane and its Dinuclear Zinc(II) Chloride Complex

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