Intramolecular cooperativity in frustrated Lewis pairs

Körte, Leif Arne; Blomeyer, Sebastian; Heidemeyer, Shari; Mix, Andreas; Neumann, Beate; Mitzel, Norbert W.

Intramolecular cooperativity in frustrated Lewis pairs

Körte LA, Blomeyer S, Heidemeyer S, Mix A, Neumann B, Mitzel NW (2016)
CHEMICAL COMMUNICATIONS 52(64): 9949-9952.

Zeitschriftenaufsatz | Veröffentlicht | Englisch

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DOI

https://doi.org/10.1039/c6cc05228b

Autor*in

Körte, Leif Arne^UniBi; Blomeyer, Sebastian^UniBi ; Heidemeyer, Shari; Mix, Andreas^UniBi; Neumann, Beate^UniBi; Mitzel, Norbert W.^UniBi

Einrichtung

Fakultät für Chemie > Anorganische Chemie und Strukturchemie

Abstract / Bemerkung

The doubly Lewis-acid functionalised aniline PhN[(CH2)(3)B(C6F5)(2)](2) features two competing boron functions in fast exchange for binding to the central Lewis base. It shows catalytic activity typical for FLPs in H/D-scrambling and catalytic hydrogenation experiments. By contrast, the singly acid-functionalised PhMeN(CH2)(3)B(C6F5)(2) reveals a dramatically smaller catalytic activity in analogous experiments.

Erscheinungsjahr

2016

Zeitschriftentitel

CHEMICAL COMMUNICATIONS

Band

Ausgabe

Seite(n)

9949-9952

ISSN

1359-7345

eISSN

1364-548X

Page URI

https://pub.uni-bielefeld.de/record/2905963

Zitieren

Körte LA, Blomeyer S, Heidemeyer S, Mix A, Neumann B, Mitzel NW. Intramolecular cooperativity in frustrated Lewis pairs. CHEMICAL COMMUNICATIONS. 2016;52(64):9949-9952.

Körte, L. A., Blomeyer, S., Heidemeyer, S., Mix, A., Neumann, B., & Mitzel, N. W. (2016). Intramolecular cooperativity in frustrated Lewis pairs. CHEMICAL COMMUNICATIONS, 52(64), 9949-9952. doi:10.1039/c6cc05228b

Körte, Leif Arne, Blomeyer, Sebastian, Heidemeyer, Shari, Mix, Andreas, Neumann, Beate, and Mitzel, Norbert W. 2016. “Intramolecular cooperativity in frustrated Lewis pairs”. CHEMICAL COMMUNICATIONS 52 (64): 9949-9952.

Körte, L. A., Blomeyer, S., Heidemeyer, S., Mix, A., Neumann, B., and Mitzel, N. W. (2016). Intramolecular cooperativity in frustrated Lewis pairs. CHEMICAL COMMUNICATIONS 52, 9949-9952.

Körte, L.A., et al., 2016. Intramolecular cooperativity in frustrated Lewis pairs. CHEMICAL COMMUNICATIONS, 52(64), p 9949-9952.

L.A. Körte, et al., “Intramolecular cooperativity in frustrated Lewis pairs”, CHEMICAL COMMUNICATIONS, vol. 52, 2016, pp. 9949-9952.

Körte, L.A., Blomeyer, S., Heidemeyer, S., Mix, A., Neumann, B., Mitzel, N.W.: Intramolecular cooperativity in frustrated Lewis pairs. CHEMICAL COMMUNICATIONS. 52, 9949-9952 (2016).

Körte, Leif Arne, Blomeyer, Sebastian, Heidemeyer, Shari, Mix, Andreas, Neumann, Beate, and Mitzel, Norbert W. “Intramolecular cooperativity in frustrated Lewis pairs”. CHEMICAL COMMUNICATIONS 52.64 (2016): 9949-9952.

3 Zitationen in Europe PMC

Daten bereitgestellt von Europe PubMed Central.

FLP catalysis: main group hydrogenations of organic unsaturated substrates.
Lam J, Szkop KM, Mosaferi E, Stephan DW., Chem Soc Rev 48(13), 2019
PMID: 30178796

CO/CO and NO/NO coupling at a hidden frustrated Lewis pair template.
Wang T, Wang L, Daniliuc CG, Samigullin K, Wagner M, Kehr G, Erker G., Chem Sci 8(3), 2017
PMID: 28451352

Intramolecular Lewis pairs with two acid sites - reactivity differences between P- and N-based systems.
Körte LA, Blomeyer S, Heidemeyer S, Nissen JH, Mix A, Neumann B, Stammler HG, Mitzel NW., Dalton Trans 45(43), 2016
PMID: 27722531

46 References

Daten bereitgestellt von Europe PubMed Central.

Reversible, metal-free hydrogen activation.
Welch GC, San Juan RR, Masuda JD, Stephan DW., Science 314(5802), 2006
PMID: 17110572

Metal-free catalytic hydrogenation.
Chase PA, Welch GC, Jurca T, Stephan DW., Angew. Chem. Int. Ed. Engl. 46(42), 2007
PMID: 17696181

Frustrated Lewis pairs: a new strategy to small molecule activation and hydrogenation catalysis.
Stephan DW., Dalton Trans (17), 2009
PMID: 19421613

Frustrated Lewis pairs: metal-free hydrogen activation and more.
Stephan DW, Erker G., Angew. Chem. Int. Ed. Engl. 49(1), 2010
PMID: 20025001

Frustrated Lewis pair chemistry: development and perspectives.
Stephan DW, Erker G., Angew. Chem. Int. Ed. Engl. 54(22), 2015
PMID: 25974714

Frustrated Lewis Pairs.
Stephan DW., J. Am. Chem. Soc. 137(32), 2015
PMID: 26214241

Facile heterolytic cleavage of dihydrogen by phosphines and boranes.
Welch GC, Stephan DW., J. Am. Chem. Soc. 129(7), 2007
PMID: 17260994

Hydrogen activation by 2-boryl-N,N-dialkylanilines: a revision of Piers' ansa-aminoborane.
Chernichenko K, Nieger M, Leskela M, Repo T., Dalton Trans 41(30), 2012
PMID: 22735769

Schwendemann, Chem. Sci. 2(), 2011

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

Metal-free catalytic hydrogenation of enamines, imines, and conjugated phosphinoalkenylboranes.
Spies P, Schwendemann S, Lange S, Kehr G, Frohlich R, Erker G., Angew. Chem. Int. Ed. Engl. 47(39), 2008
PMID: 18726976

Structural importance of secondary interactions in molecules: origin of unconventional conformations of phosphine-borane adducts.
Spies P, Frohlich R, Kehr G, Erker G, Grimme S., Chemistry 14(1), 2008
PMID: 17896334

Metal-free dihydrogen activation chemistry: structural and dynamic features of intramolecular P/B pairs.
Spies P, Kehr G, Bergander K, Wibbeling B, Frohlich R, Erker G., Dalton Trans (9), 2009
PMID: 19421595

Rapid intramolecular heterolytic dihydrogen activation by a four-membered heterocyclic phosphane-borane adduct.
Spies P, Erker G, Kehr G, Bergander K, Frohlich R, Grimme S, Stephan DW., Chem. Commun. (Camb.) (47), 2007
PMID: 18049757

Why Does the Intramolecular Trimethylene-Bridged Frustrated Lewis Pair Mes2 PCH2 CH2 CH2 B(C6 F5 )2 Not Activate Dihydrogen?
Ozgun T, Ye KY, Daniliuc CG, Wibbeling B, Liu L, Grimme S, Kehr G, Erker G., Chemistry 22(17), 2016
PMID: 26999779

Facile splitting of hydrogen and ammonia by nucleophilic activation at a single carbon center.
Frey GD, Lavallo V, Donnadieu B, Schoeller WW, Bertrand G., Science 316(5823), 2007
PMID: 17446400

Hydrogen and amine activation by a frustrated Lewis pair of a bulky N-heterocyclic carbene and B(C6F5)3.
Chase PA, Stephan DW., Angew. Chem. Int. Ed. Engl. 47(39), 2008
PMID: 18655208

Activation of H2 by phosphinoboranes R2PB(C6F5)2.
Geier SJ, Gilbert TM, Stephan DW., J. Am. Chem. Soc. 130(38), 2008
PMID: 18754584

Reversible metal-free carbon dioxide binding by frustrated Lewis pairs.
Momming CM, Otten E, Kehr G, Frohlich R, Grimme S, Stephan DW, Erker G., Angew. Chem. Int. Ed. Engl. 48(36), 2009
PMID: 19569151

Sajid, Chem. Sci. 4(), 2013

C-H bond activation by radical ion pairs derived from R3P/Al(C6F5)3 frustrated Lewis pairs and N2O.
Menard G, Hatnean JA, Cowley HJ, Lough AJ, Rawson JM, Stephan DW., J. Am. Chem. Soc. 135(17), 2013
PMID: 23594345

Reaction of a P/Al-based frustrated Lewis pair with ammonia, borane, and amine-boranes: adduct formation and catalytic dehydrogenation.
Appelt C, Slootweg JC, Lammertsma K, Uhl W., Angew. Chem. Int. Ed. Engl. 52(15), 2013
PMID: 23471587

A P-H Functionalized Al/P Frustrated Lewis Pair: Substrate Activation and Selective Hydrogen Transfer.
Keweloh L, Klocker H, Wurthwein EU, Uhl W., Angew. Chem. Int. Ed. Engl. 55(9), 2016
PMID: 26836748

Dihydrogen activation by a silylium silylene frustrated Lewis pair and the unexpected isomerization reaction of a protonated silylene.
Schafer A, Reißmann M, Schafer A, Schmidtmann M, Muller T., Chemistry 20(30), 2014
PMID: 24942460

Reißmann, Organometallics 32(), 2013

Activation of Carbon Dioxide by Silyl Triflate-Based Frustrated Lewis Pairs.
Weicker SA, Stephan DW., Chemistry 21(37), 2015
PMID: 26223404

A Neutral Silicon/Phosphorus Frustrated Lewis Pair.
Waerder B, Pieper M, Korte LA, Kinder TA, Mix A, Neumann B, Stammler HG, Mitzel NW., Angew. Chem. Int. Ed. Engl. 54(45), 2015
PMID: 26423202

Dobrovetsky, Isr. J. Chem. 55(), 2015

H2 cleavage, hydride formation, and catalytic hydrogenation of imines with zinc complexes of C5Me5 and N-heterocyclic carbenes.
Jochmann P, Stephan DW., Angew. Chem. Int. Ed. Engl. 52(37), 2013
PMID: 23868720

Frustrated Lewis pairs beyond the main group: cationic zirconocene-phosphinoaryloxide complexes and their application in catalytic dehydrogenation of amine boranes.
Chapman AM, Haddow MF, Wass DF., J. Am. Chem. Soc. 133(23), 2011
PMID: 21548587

Frustrated Lewis pairs beyond the main group: synthesis, reactivity, and small molecule activation with cationic zirconocene-phosphinoaryloxide complexes.
Chapman AM, Haddow MF, Wass DF., J. Am. Chem. Soc. 133(45), 2011
PMID: 21958011

Small Molecule Activation by Intermolecular Zr(IV)-Phosphine Frustrated Lewis Pairs.
Metters OJ, Forrest SJ, Sparkes HA, Manners I, Wass DF., J. Am. Chem. Soc. 138(6), 2016
PMID: 26788963

Metal-free hydrogen activation and hydrogenation of imines by 1,8-bis(dipentafluorophenylboryl)naphthalene.
Jiang C, Blacque O, Berke H., Chem. Commun. (Camb.) (37), 2009
PMID: 19753342

Lewis acid-catalyzed hydrogenation: B(C6F5)3-mediated reduction of imines and nitriles with H2.
Chase PA, Jurca T, Stephan DW., Chem. Commun. (Camb.) (14), 2008
PMID: 18368170

On the mechanism of B(C6F5)3-catalyzed direct hydrogenation of imines: inherent and thermally induced frustration.
Rokob TA, Hamza A, Stirling A, Papai I., J. Am. Chem. Soc. 131(5), 2009
PMID: 19159259

Combinations of ethers and B(C6F5)3 function as hydrogenation catalysts.
Hounjet LJ, Bannwarth C, Garon CN, Caputo CB, Grimme S, Stephan DW., Angew. Chem. Int. Ed. Engl. 52(29), 2013
PMID: 23775686

Assisted tandem catalytic RCM-aromatization in the synthesis of pyrroles and furans.
Schmidt B, Krehl S, Jablowski E., Org. Biomol. Chem. 10(26), 2012
PMID: 22622871

Parks, Organometallics 17(), 1998

Parks, Angew. Chem., Int. Ed. 34(), 1995

Inherent stability limits of intramolecular boron nitrogen Lewis acid-base pairs.
Winkelhaus D, Neumann B, Stammler HG, Berger RJ, Vishnevskiy YV, Mitzel NW., Chemistry 18(30), 2012
PMID: 22707351

Sandström, 1982

Ōki, 1985

Kintzinger, Mol. Phys. 14(), 1968

Brown, J. Org. Chem. 55(), 1990

Intramolecular pyridine-based frustrated Lewis-pairs.
Korte LA, Warner R, Vishnevskiy YV, Neumann B, Stammler HG, Mitzel NW., Dalton Trans 44(21), 2015
PMID: 25952677

Rationalizing the reactivity of frustrated Lewis pairs: thermodynamics of H(2) activation and the role of acid-base properties.
Rokob TA, Hamza A, Papai I., J. Am. Chem. Soc. 131(30), 2009
PMID: 19722636

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Phasenabhängige Strukturchemie - Struktur-Reaktivitäts-Beziehungen und nicht-kovalente Wechselwirkungen
Blomeyer S (2017)
Bielefeld.

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