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.

Download
No fulltext has been uploaded. References only!
Journal Article | Original Article | Published | English

No fulltext has been uploaded

Abstract / Notes
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.
Publishing Year
ISSN
eISSN
PUB-ID

Cite this

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, 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.
This data publication is cited in the following publications:
This publication cites the following data publications:

10 Citations in Europe PMC

Data provided by 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
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
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
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
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
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
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
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

50 References

Data provided by Europe PubMed Central.


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

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

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), 2010
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

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

0 Marked Publications

Open Data PUB

Web of Science

View record in Web of Science®

Sources

PMID: 22688949
PubMed | Europe PMC

Search this title in

Google Scholar