Intramolecular Lewis acid-base pairs based on 4-ethynyl-2,6-lutidine
Winkelhaus D, Neumann B, Stammler H-G, Mitzel NW (2012)
Dalton Transactions 41(30): 9143-9150.
Zeitschriftenaufsatz
| Veröffentlicht | Englisch
Download
Es wurden keine Dateien hochgeladen. Nur Publikationsnachweis!
Autor*in
Abstract / Bemerkung
The reaction of 4-ethynyl-2,6-lutidine, (2,6-Me-2)(4-HC=C)C5H2N (2), with B(C6F5)(3) afforded the zwitterion [(2,6-Me-2)(4-(C6F5)(3)BC C)C5H2NH] (3) via a deprotonation pathway. By treatment of 2 with the group 13 trialkyls AlMe3, AlEt3, GaMe3, GaEt3 and InMe3, metallation of the ethynyl group afforded compounds 4-8 under extrusion of the corresponding alkane. The resulting products were characterised by elemental analyses and NMR spectroscopy. Compounds 4 and 8 were crystallized from THF and were yielded as monomers with coordinated THF molecules. The gallium compound 7 could be crystallised from benzene and was afforded as coordination polymer. The structures of these three compounds (4 . THF, 7 and 8 . 2THF) were determined by single-crystal X-ray diffraction experiments. The aluminium compounds 4 and 5 show redistribution reaction of their substituents.
Erscheinungsjahr
2012
Zeitschriftentitel
Dalton Transactions
Band
41
Ausgabe
30
Seite(n)
9143-9150
ISSN
1477-9226
eISSN
1477-9234
Page URI
https://pub.uni-bielefeld.de/record/2518101
Zitieren
Winkelhaus D, Neumann B, Stammler H-G, Mitzel NW. Intramolecular Lewis acid-base pairs based on 4-ethynyl-2,6-lutidine. Dalton Transactions. 2012;41(30):9143-9150.
Winkelhaus, D., Neumann, B., Stammler, H. - G., & Mitzel, N. W. (2012). Intramolecular Lewis acid-base pairs based on 4-ethynyl-2,6-lutidine. Dalton Transactions, 41(30), 9143-9150. doi:10.1039/c2dt30719g
Winkelhaus, Daniel, Neumann, Beate, Stammler, Hans-Georg, and Mitzel, Norbert W. 2012. “Intramolecular Lewis acid-base pairs based on 4-ethynyl-2,6-lutidine”. Dalton Transactions 41 (30): 9143-9150.
Winkelhaus, D., Neumann, B., Stammler, H. - G., and Mitzel, N. W. (2012). Intramolecular Lewis acid-base pairs based on 4-ethynyl-2,6-lutidine. Dalton Transactions 41, 9143-9150.
Winkelhaus, D., et al., 2012. Intramolecular Lewis acid-base pairs based on 4-ethynyl-2,6-lutidine. Dalton Transactions, 41(30), p 9143-9150.
D. Winkelhaus, et al., “Intramolecular Lewis acid-base pairs based on 4-ethynyl-2,6-lutidine”, Dalton Transactions, vol. 41, 2012, pp. 9143-9150.
Winkelhaus, D., Neumann, B., Stammler, H.-G., Mitzel, N.W.: Intramolecular Lewis acid-base pairs based on 4-ethynyl-2,6-lutidine. Dalton Transactions. 41, 9143-9150 (2012).
Winkelhaus, Daniel, Neumann, Beate, Stammler, Hans-Georg, and Mitzel, Norbert W. “Intramolecular Lewis acid-base pairs based on 4-ethynyl-2,6-lutidine”. Dalton Transactions 41.30 (2012): 9143-9150.
Daten bereitgestellt von European Bioinformatics Institute (EBI)
10 Zitationen in Europe PMC
Daten bereitgestellt von Europe PubMed Central.
From Bidentate Gallium Lewis Acids to Supramolecular Complexes.
Horstmann J, Hyseni M, Mix A, Neumann B, Stammler HG, Mitzel NW., Angew Chem Int Ed Engl 56(22), 2017
PMID: 28418175
Horstmann J, Hyseni M, Mix A, Neumann B, Stammler HG, Mitzel NW., Angew Chem Int Ed Engl 56(22), 2017
PMID: 28418175
Trans-Metal-Trapping Meets Frustrated-Lewis-Pair Chemistry: Ga(CH2SiMe3)3-Induced C-H Functionalizations.
Uzelac M, Kennedy AR, Hevia E., Inorg Chem 56(15), 2017
PMID: 28485929
Uzelac M, Kennedy AR, Hevia E., Inorg Chem 56(15), 2017
PMID: 28485929
Five-component trigonal nanoprism with six dynamic corners.
Gaikwad S, Lal Saha M, Samanta D, Schmittel M., Chem Commun (Camb) 53(57), 2017
PMID: 28671227
Gaikwad S, Lal Saha M, Samanta D, Schmittel M., Chem Commun (Camb) 53(57), 2017
PMID: 28671227
Tridentate Lewis acids with phenyl substituted 1,3,5-trisilacyclohexane backbones.
Weisheim E, Bücker L, Neumann B, Stammler HG, Mitzel NW., Dalton Trans 45(1), 2016
PMID: 26599621
Weisheim E, Bücker L, Neumann B, Stammler HG, Mitzel NW., Dalton Trans 45(1), 2016
PMID: 26599621
Understanding the Subtleties of Frustrated Lewis Pair Activation of Carbonyl Compounds by N-Heterocyclic Carbene/Alkyl Gallium Pairings.
Uzelac M, Armstrong DR, Kennedy AR, Hevia E., Chemistry 22(44), 2016
PMID: 27666145
Uzelac M, Armstrong DR, Kennedy AR, Hevia E., Chemistry 22(44), 2016
PMID: 27666145
Indirect synthesis of a pair of formal methane activation products at a phosphane/borane frustrated Lewis pair.
Frömel S, Daniliuc CG, Bannwarth C, Grimme S, Bussmann K, Kehr G, Erker G., Dalton Trans 45(48), 2016
PMID: 27872934
Frömel S, Daniliuc CG, Bannwarth C, Grimme S, Bussmann K, Kehr G, Erker G., Dalton Trans 45(48), 2016
PMID: 27872934
Σ- versus π-activation of alkynyl benzoates using B(C₆F₅)₃.
Bähr A, Wilkins LC, Ollegott K, Kariuki BM, Melen RL., Molecules 20(3), 2015
PMID: 25774488
Bähr A, Wilkins LC, Ollegott K, Kariuki BM, Melen RL., Molecules 20(3), 2015
PMID: 25774488
Tridentate Lewis Acids Based on 1,3,5-Trisilacyclohexane Backbones and an Example of Their Host-Guest Chemistry.
Weisheim E, Reuter CG, Heinrichs P, Vishnevskiy YV, Mix A, Neumann B, Stammler HG, Mitzel NW., Chemistry 21(35), 2015
PMID: 26213228
Weisheim E, Reuter CG, Heinrichs P, Vishnevskiy YV, Mix A, Neumann B, Stammler HG, Mitzel NW., Chemistry 21(35), 2015
PMID: 26213228
A frustrated-Lewis-pair approach to catalytic reduction of alkynes to cis-alkenes.
Chernichenko K, Madarász A, Pápai I, Nieger M, Leskelä M, Repo T., Nat Chem 5(8), 2013
PMID: 23881505
Chernichenko K, Madarász A, Pápai I, Nieger M, Leskelä M, Repo T., Nat Chem 5(8), 2013
PMID: 23881505
Cyclisation versus 1,1-Carboboration: Reactions of B(C6F5)3 with Propargyl Amides.
Melen RL, Hansmann MM, Lough AJ, Hashmi AS, Stephan DW., Chemistry 19(36), 2013
PMID: 23922200
Melen RL, Hansmann MM, Lough AJ, Hashmi AS, Stephan DW., Chemistry 19(36), 2013
PMID: 23922200
50 References
Daten bereitgestellt von Europe PubMed Central.
Activation of dihydrogen by non-metal systems.
Stephan DW., Chem. Commun. (Camb.) 46(45), 2010
PMID: 20967357
Stephan DW., Chem. Commun. (Camb.) 46(45), 2010
PMID: 20967357
Stephan, Angew. Chem. 122(), 2010
Reversible, metal-free hydrogen activation.
Welch GC, San Juan RR, Masuda JD, Stephan DW., Science 314(5802), 2006
PMID: 17110572
Welch GC, San Juan RR, Masuda JD, Stephan DW., Science 314(5802), 2006
PMID: 17110572
Facile heterolytic cleavage of dihydrogen by phosphines and boranes.
Welch GC, Stephan DW., J. Am. Chem. Soc. 129(7), 2007
PMID: 17260994
Welch GC, Stephan DW., J. Am. Chem. Soc. 129(7), 2007
PMID: 17260994
Spies, Chem. Commun. (), 2007
Reversible, metal-free, heterolytic activation of H2 at room temperature.
Ullrich M, Lough AJ, Stephan DW., J. Am. Chem. Soc. 131(1), 2009
PMID: 19061321
Ullrich M, Lough AJ, Stephan DW., J. Am. Chem. Soc. 131(1), 2009
PMID: 19061321
Ullrich, Organometallics 29(), 2010
Mömming, Angew. Chem. 121(), 2009
Ménard, Angew. Chem. 123(), 2011
Tandem frustrated Lewis pair/tris(pentafluorophenyl)borane-catalyzed deoxygenative hydrosilylation of carbon dioxide.
Berkefeld A, Piers WE, Parvez M., J. Am. Chem. Soc. 132(31), 2010
PMID: 20681691
Berkefeld A, Piers WE, Parvez M., J. Am. Chem. Soc. 132(31), 2010
PMID: 20681691
Complexation of nitrous oxide by frustrated Lewis pairs.
Otten E, Neu RC, Stephan DW., J. Am. Chem. Soc. 131(29), 2009
PMID: 19569691
Otten E, Neu RC, Stephan DW., J. Am. Chem. Soc. 131(29), 2009
PMID: 19569691
Neu, Chem. Sci. 2(), 2011
Neu, Angew. Chem. 121(), 2009
Brown, J. Am. Chem. Soc. 64(), 1942
Lutidine/B(C6F5)3: at the boundary of classical and frustrated Lewis pair reactivity.
Geier SJ, Stephan DW., J. Am. Chem. Soc. 131(10), 2009
PMID: 19243095
Geier SJ, Stephan DW., J. Am. Chem. Soc. 131(10), 2009
PMID: 19243095
Reactions of substituted pyridines with electrophilic boranes.
Caputo CB, Geier SJ, Winkelhaus D, Mitzel NW, Vukotic VN, Loeb SJ, Stephan DW., Dalton Trans 41(7), 2011
PMID: 22186932
Caputo CB, Geier SJ, Winkelhaus D, Mitzel NW, Vukotic VN, Loeb SJ, Stephan DW., Dalton Trans 41(7), 2011
PMID: 22186932
Spies, Angew. Chem. 120(), 2008
Sumerin, Angew. Chem. 120(), 2008
Sumerin, J. Organomet. Chem. 694(), 2009
Chase, Chem. Commun. (), 2008
Molecular tweezers for hydrogen: synthesis, characterization, and reactivity.
Sumerin V, Schulz F, Atsumi M, Wang C, Nieger M, Leskela M, Repo T, Pyykko P, Rieger B., J. Am. Chem. Soc. 130(43), 2008
PMID: 18826306
Sumerin V, Schulz F, Atsumi M, Wang C, Nieger M, Leskela M, Repo T, Pyykko P, Rieger B., J. Am. Chem. Soc. 130(43), 2008
PMID: 18826306
Metal-free catalytic hydrogenation of polar substrates by frustrated Lewis pairs.
Stephan DW, Greenberg S, Graham TW, Chase P, Hastie JJ, Geier SJ, Farrell JM, Brown CC, Heiden ZM, Welch GC, Ullrich M., Inorg Chem 50(24), 2011
PMID: 21534552
Stephan DW, Greenberg S, Graham TW, Chase P, Hastie JJ, Geier SJ, Farrell JM, Brown CC, Heiden ZM, Welch GC, Ullrich M., Inorg Chem 50(24), 2011
PMID: 21534552
Welch, Dalton Trans. (), 2007
McCahill, Angew. Chem. 119(), 2007
Voss, Chem.–Eur. J. 16(), 2010
Ullrich, Chem. Commun. (), 2009
Terminal alkyne activation by frustrated and classical Lewis acid/phosphine pairs.
Dureen MA, Stephan DW., J. Am. Chem. Soc. 131(24), 2009
PMID: 19485368
Dureen MA, Stephan DW., J. Am. Chem. Soc. 131(24), 2009
PMID: 19485368
Jiang, Organometallics 29(), 2010
Uhl, Z. Anorg. Allg. Chem. 630(), 2004
Uhl, Z. Anorg. Allg. Chem. 632(), 2006
Uhl, Eur. J. Inorg. Chem. (), 2009
Chmiel, Chem.–Eur. J. 16(), 2010
Sonogashira, Tetrahedron Lett. 16(), 1975
Kenkichi, J. Organomet. Chem. 653(), 2002
The Sonogashira reaction: a booming methodology in synthetic organic chemistry.
Chinchilla R, Najera C., Chem. Rev. 107(3), 2007
PMID: 17305399
Chinchilla R, Najera C., Chem. Rev. 107(3), 2007
PMID: 17305399
Yamamoto, Chem. Pharm. Bull. 30(), 1982
Di-substituted pyridinyl aminohydantoins as potent and highly selective human beta-secretase (BACE1) inhibitors.
Malamas MS, Barnes K, Johnson M, Hui Y, Zhou P, Turner J, Hu Y, Wagner E, Fan K, Chopra R, Olland A, Bard J, Pangalos M, Reinhart P, Robichaud AJ., Bioorg. Med. Chem. 18(2), 2009
PMID: 20045648
Malamas MS, Barnes K, Johnson M, Hui Y, Zhou P, Turner J, Hu Y, Wagner E, Fan K, Chopra R, Olland A, Bard J, Pangalos M, Reinhart P, Robichaud AJ., Bioorg. Med. Chem. 18(2), 2009
PMID: 20045648
Ohkita, Chem. Commun. (), 2001
Mootz, J. Chem. Phys. 75(), 1981
Schnitter, Chem.–Eur. J. 3(), 1997
Haaland, J. Organomet. Chem. 134(), 1977
Fernholt, Acta Chem. Scand., Ser. A 35a(), 1981
Westerhausen, Z. Anorg. Allg. Chem. 630(), 2004
Modelling fundamental arene-borane contacts: spontaneous formation of a dibromoborenium cation driven by interaction between a borane Lewis acid and an arene π system.
Mansaray HB, Rowe AD, Phillips N, Niemeyer J, Kelly M, Addy DA, Bates JI, Aldridge S., Chem. Commun. (Camb.) 47(45), 2011
PMID: 22012242
Mansaray HB, Rowe AD, Phillips N, Niemeyer J, Kelly M, Addy DA, Bates JI, Aldridge S., Chem. Commun. (Camb.) 47(45), 2011
PMID: 22012242
Golubinskaya, J. Organomet. Chem. 117(), 1976
Mitzel, Angew. Chem. 114(), 2002
Schumann, J. Organomet. Chem. 479(), 1994
Lewiński, Organometallics 24(), 2005
Singh, J. Heterocycl. Chem. 27(), 1990
Sheldrick, Acta Crystallogr., Sect. A: Fundam. Crystallogr. A64(), 2008
Export
Markieren/ Markierung löschen
Markierte Publikationen
Web of Science
Dieser Datensatz im Web of Science®Quellen
PMID: 22688949
PubMed | Europe PMC
Suchen in
Google Scholar