Synthesis 2017; 49(01): 53-58
DOI: 10.1055/s-0036-1588597
paper
© Georg Thieme Verlag Stuttgart · New York

Synthesis of a Small Cyclic Frustrated Phosphane/Borane Lewis Pair

Juri Ugolotti
a   Organisch-Chemisches Institut, Westfälische Wilhelms-Universität, Corrensstraße 40, 48149 Münster, Germany
b   Regional Centre of Advanced Technologies and Materials, Palacky University, Šlechtitelů 27, 78371 Olomouc, Czech Republic   Email: erker@uni-muenster.de
,
Gerald Kehr
a   Organisch-Chemisches Institut, Westfälische Wilhelms-Universität, Corrensstraße 40, 48149 Münster, Germany
,
Constantin G. Daniliuc
a   Organisch-Chemisches Institut, Westfälische Wilhelms-Universität, Corrensstraße 40, 48149 Münster, Germany
,
Gerhard Erker*
a   Organisch-Chemisches Institut, Westfälische Wilhelms-Universität, Corrensstraße 40, 48149 Münster, Germany
› Author Affiliations
Further Information

Publication History

Received: 12 August 2016

Accepted after revision: 30 August 2016

Publication Date:
21 September 2016 (online)


§ X-ray crystal structure analysis

Dedicated to Professor Dieter Enders on the occasion of his 70th birthday

Abstract

Treatment of pyrrolidinodivinylphosphane with three molar equivalents of bis(pentafluorophenyl)borane resulted in the formation of a bicyclic pyrrolidino-bridged P/B frustrated Lewis pair (FLP) derivative, isolated as its P–[HB(C6F5)2] adduct. The system can be converted into an unbridged cyclic P/B frustrated Lewis pair derivative by the addition of pyridine.

Supporting Information

 
  • References

    • 1a Pedersen CL. Angew. Chem., Int. Ed. Engl. 1988; 27: 1021
    • 1b Cram DJ. Angew. Chem., Int. Ed. Engl. 1988; 27: 1009
    • 1c Crown Ethers and Analogous Compounds. In Studies in Organic Chemistry. Vol. 45. Hiraoka M. Elsevier; Amsterdam: 1992: 1
    • 2a Lehn JM. Acc. Chem. Res. 1978; 11: 49
    • 2b Carminade A.-M, Majoral JP. Chem. Rev. 1994; 94: 1183
    • 2c Han Y, Jiang Y, Chen C.-F. Tetrahedron 2015; 71: 503

      See also:
    • 3a Gray GM. Comments Inorg. Chem. 1995; 17: 95
    • 3b Gokel GW, Leevy WM, Weber ME. Chem. Rev. 2004; 104: 2723
  • 4 Kang SO, Llinares JM, Day VW, Bowman-Jones K. Chem. Soc. Rev. 2010; 39: 3980
    • 5a Stephan DW, Erker G. Angew. Chem. Int. Ed. 2015; 54: 6400
    • 5b Frustrated Lewis Pairs I, Uncovering and Understanding. In Topics in Current Chemistry. Vol. 332. Stephan DW, Erker G. Springer; Heidelberg: 2013
    • 5c Frustrated Lewis Pairs II, Expanding the Scope . In Topics in Current Chemistry . Vol. 334. Stephan DW, Erker G. Springer; Heidelberg: 2013
    • 6a Welch GC, Juan RR. S, Masuda JD, Stephan DW. Science (Washington, D. C.) 2006; 314: 1124
    • 6b Welch GC, Stephan DW. J. Am. Chem. Soc. 2007; 129: 1880
    • 6c Spies P, Erker G, Kehr G, Bergander K, Fröhlich R, Grimme S, Stephan DW. Chem. Commun. 2007; 5072
    • 7a Spies P, Schwendemann S, Lange S, Kehr G, Fröhlich R, Erker G. Angew. Chem. Int. Ed. 2008; 47: 7543
    • 7b Wang H, Fröhlich R, Kehr G, Erker G. Chem. Commun. 2008; 5966
    • 7c Reddy JS, Xu B.-H, Mahdi T, Fröhlich R, Kehr G, Stephan DW, Erker G. Organometallics 2012; 31: 5638
    • 7d Scott DJ, Fuchter MJ, Ashley AE. J. Am. Chem. Soc. 2014; 136: 15813
    • 8a Parks DJ, von H Spence RE, Piers WE. Angew. Chem., Int. Ed. Engl. 1995; 34: 809
    • 8b von H Spence RE, Piers WE, Sun Y, Parvez M, McGillivray LR, Zaworotko MJ. Organometallics 1998; 17: 2459
  • 9 Liedtke R, Tenberge F, Daniliuc CG, Kehr G, Erker G. J. Org. Chem. 2015; 80: 2240
  • 10 Erdmann M, Rösener C, Holtrichter-Rößmann T, Daniliuc CG, Fröhlich R, Uhl W, Würthwein E.-U, Kehr G, Erker G. Dalton Trans. 2013; 42: 709

    • Formally this would correspond to the reaction of compound 3a with H2BC6F5; see for example:
    • 11a Jiang C, Blacque O, Berke H. Organometallics 2009; 28: 5233
    • 11b Fuller A.-M, Hughes DL, Lancaster SJ, White CM. Organometallics 2010; 29: 2194
    • 11c Jacobs EA, Chandrasekar R, Smith DA, White CM, Bochmann M, Lancaster SJ. J. Organomet. Chem. 2013; 730: 44
    • 11d Wang T, Liu L, Grimme S, Daniliuc CG, Kehr G, Erker G. Chem. Asian J. 2016; 11: 1394
  • 12 Hooft RW. W. Bruker AXS. Delft; The Netherlands: 2008
  • 13 Otwinowski Z, Minor W. Methods Enzymol. 1997; 276: 307
  • 14 Otwinowski Z, Borek D, Majewski W, Minor W. Acta Crystallogr., Sect. A 2003; 59: 228
  • 15 Sheldrick GM. Acta Crystallogr., Sect. A 1990; 46: 467
  • 16 Sheldrick GM. Acta Crystallogr., Sect. A. 2008; 64: 112
  • 17 Spek AL. J. Appl. Crystallogr. 2003; 36: 7
  • 18 Parks DJ, Piers WE, Yap GP. A. Organometallics 1998; 17: 5492
    • 19a Markl G, Alig B. J. Organomet. Chem. 1984; 273: 1
    • 19b Bowen LE, Charernsuk M, Hey TW, McMullin CL, Orpen AG, Wass DF. Dalton Trans. 2010; 39: 560
  • 20 King RB, Masler WF. J. Am. Chem. Soc. 1977; 99: 4001