Synthesis 2023; 55(02): 347-353
DOI: 10.1055/a-1840-5680
paper
Special Issue dedicated to Prof. Alain Krief

A Selenenium-Bridged 10-Boratriptycene Lewis Acid

Arnaud Osi
,
Nikolay Tumanov
,
Johan Wouters
,
Aurélien Chardon
,
We acknowledge the University of Namur, the Namur Institute of Structured Matter (NISM) and the Fond National de la Recherche Scientifique (FRS-FNRS) for financial support (grant Nos.: F.4513.18 and T.0012.21 (G.B.), Fonds pour la Formation à la Recherche dans l’Industrie et dans l’Agriculture (FRIA) Ph.D. grant for A.O. (1.E.097.20), and Chargé de recherche - Fonds De La Recherche Scientifique research grant for A.C. (1.B.087.21F).


Dedicated to Prof Alain Krief for his 80th birthday.

Abstract

A non-planar triarylborane and a new member of the boratriptycene family bearing a selenium atom in bridgehead position of triptycene scaffold was generated and isolated as a boron-‘ate’ complex paired with a weakly coordinating anion. With similar electronegativity while possessing longer atom radius with respect to sulfur, the introduction a selenium atom, in the form of a selenenium moiety, at the bridgehead of a triptycene scaffold allows a very precise modification of the pyramidalization of the boron atom environment. Experimental and computational evaluation of the Lewis acidity of this new boratriptycene derivative gave qualitative information on how a modification of the pyramidalization of the boron environment affects alone Lewis acidity parameters of such pyramidal triarylborane.

Supporting Information



Publication History

Received: 21 March 2022

Accepted after revision: 02 May 2022

Accepted Manuscript online:
02 May 2022

Article published online:
09 June 2022

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  • References

    • 1a Wakami A, Yamaguchi S. Bull. Chem. Soc. Jpn. 2015; 88: 1357
    • 1b Piers WE, Chivers T. Chem. Soc. Rev. 1997; 26: 345
    • 1c Piers WE. Adv. Org. Chem. 2004; 52: 1
    • 1d Berger S, Ferger MM, Marder TB. Chem. Eur. J. 2021; 27: 7043
    • 2a Legaré MA, Pranckevicius C, Braunschweig H. Chem. Rev. 2019; 119: 8231
    • 2b Boron: Sensing, Synthesis and Supramolecular Self-assembly . Li M, Fossey J, James TD. Royal Society of Chemistry; Cambridge: 2015
    • 2c Erker G. Dalton Trans. 2005; 1883

    • For recent reviews see:
    • 2d Wade CR, Broomsgrove AE. J, Aldridge S, Gabbaï F. Chem. Rev. 2010; 110: 3958
    • 2e Jäkle F. Chem. Rev. 2010; 110: 3985
    • 2f Lorbach A, Hübner A, Wagner M. Dalton Trans. 2012; 41: 6048
    • 2g Ji L, Griesbeck S, Marder TB. Chem. Sci. 2017; 8: 846
    • 2h Hirai M, Tanaka N, Sakai M, Yamaguchi S. Chem. Rev. 2019; 119: 8191

    • For major reviews concerning frustrated Lewis pairs see:
    • 2i Stephan DW, Erker G. Angew. Chem. Int. Ed. 2010; 49: 46
    • 2j Stephan DW. Science 2016; 354: 1248

    • For miscellaneous applications see:
    • 2k Xian N, Wang WQ, Wu ZY, Chen S, Tan W, Sui YX, Wang XP, Jiang J, Power PP. Chem. Commun. 2016; 52: 12714
    • 2l Guo J, Yang Y, Du C, Wang J. J. Am. Chem. Soc. 2021; 143: 18272
    • 2m Zheng Y, Xiong J, Sun Y, Pan X, Wu J. Angew. Chem. Int. Ed. 2015; 54: 12933
    • 2n Li J, Edkins RM, Lorbach A, Krummenacher I, Brückner C, Eichorn A, Braunschweig H, Engels B, Low PJ, Marder TB. J. Am. Chem. Soc. 2015; 137: 6750
    • 2o Rauch F, Fuchs S, Friedrich A, Sieh D, Krummenacher I, Braunschweig H, Finze M, Marder TB. Chem. Eur. J. 2020; 26: 12794
    • 2p Jia XQ, Nitsch J, Wu Z, Friedrich A, Krebs J, Krummenacher I, Braunschweig H, Moos M, Lembert C, Engels B, Marder TB. Chem. Sci. 2021; 12: 11864
    • 3a Roswell BD, Gillespie RJ, Heard GL. Inorg. Chem. 1999; 38: 4659
    • 3b Bessac F, Frenking G. Inorg. Chem. 2003; 42: 7990
    • 3c Mück LA, Timoshkin AY, Frenking G. Inorg. Chem. 2012; 51: 640
    • 3d Davydova EI, Sevsatianova TN, Timoshkin AY. Coord. Chem. Rev. 2015; 297: 91
    • 3e Mahaut D, Chardon A, Mineur L, Champagne B, Berionni G. ChemPhysChem 2021; 22: 1958
    • 3f Henkelmann M, Omlor A, Bolte M, Schünemann V, Lerner H.-W, Noga J, Hrobarik P, Wagner M. Chem. Sci. 2022; 13: 1608
    • 3g Goura J, McQuade J, Shimoyama D, Lalancette RA, Sheridan JB, Jäkle F. Chem. Commun. 2022; 58: 977
    • 3h Chardon A, Osi A, Mahaut D, Ben Saida A, Berionni G. Synlett 2020; 31: 1639

    • For recent contributions in the field of non-VSEPR main-group Lewis acids, see:
    • 3i Ebner F, Wadepohl H, Greb L. J. Am. Chem. Soc. 2019; 141: 18009
    • 3j Ebner F, Greb L. Chem 2021; 7: 2151
    • 3k Kindervater MB, Marczenko KM, Werner-Zwanziger U, Chitnis SS. Angew. Chem. Int. Ed. 2019; 58: 7850
    • 3l Marczenko KM, Zurakowski JA, Kindervater MB, Jee S, Hynes T, Roberts N, Park S, Werner-Zwanziger U, Lumsden M, Langelaan DN, Chitnis SS. Chem. Eur. J. 2019; 25: 16414
    • 3m Mondal MK, Zhang L, Feng Z, Tang S, Feng R, Zhao Y, Tan G, Ruan H, Wang X. Angew. Chem. Int. Ed. 2019; 58: 15829
    • 4a Zhou Z, Wakamiya A, Kushida T, Yamaguchi S. J. Am. Chem. Soc. 2012; 134: 4529
    • 4b Kushida T, Camacho C, Shuto A, Irle S, Muramatsu M, Katayama T, Ito S, Nagasawa Y, Miyasaka H, Sakuda E, Kitamura N, Zhou Z, Wakamiya A, Yamaguchi S. Chem. Sci. 2014; 5: 1296
    • 5a Mück LA, Timoshkin AY, von Hopffgarten M, Frenking G. J. Am. Chem. Soc. 2009; 131: 3942
    • 5b Timoshkin AY, Morokuma K. Phys. Chem. Chem. Phys. 2012; 14: 14911
    • 6a Chardon A, Osi A, Mahaut D, Doan T.-H, Tumanov M, Wouters J, Fusaro L, Champagne B, Berionni G. Angew. Chem. Int. Ed. 2020; 59: 12402
    • 6b Ben Saida A, Chardon A, Osi A, Tumanov N, Wouters J, Adjieufack AI, Champagne B, Berionni G. Angew. Chem. Int. Ed. 2019; 58: 16889
  • 7 Osi A, Mahaut D, Tumanov N, Fusaro L, Wouters J, Champagne B, Chardon A, Berionni G. Angew. Chem. Int. Ed. 2022; 61: e202112342
  • 8 Perrone D, Monteiro M, Nunes JC. In Selenium: Chemistry, Analysis, Function and Effects, Chap. 1. Preedy RP. Royal Society of Chemistry; Cambridge: 2015: 3
  • 9 Iwaoka M. In Organoselenium Chemistry: Synthesis and Reactions, Chap. 2. Wirth T. Wiley-VCH; Weinheim: 2011: 53
  • 10 Lappert MF. J. Chem. Soc. 1962; 542
    • 11a Beattie IR, Gilson T. J. Chem. Soc. 1964; 2292
    • 11b Purcell K, Drago R. J. Am. Chem. Soc. 1966; 88: 919
  • 12 Zheng B, Wang LL, Du L, Pan Y, Huang K.-W, Du HL. Mater. Horiz. 2016; 3: 355
  • 13 Woods RJ, Andrews CW, Bowen JP. J. Am. Chem. Soc. 1992; 114: 859
  • 14 Andres J, Arnau A, Bertan J, Silla E. J. Mol. Struct. 1985; 120: 315
  • 15 Sivaev B, Bregadze VI. Coord. Chem. Rev. 2014; 270: 75
    • 16a Gutmann V. Coord. Chem. Rev. 1976; 18: 225
    • 16b Beckett MA, Strickland GC, Holland JR, Sakumar VK. Polymer 1996; 37: 4629
    • 16c Erdmann P, Greb L. Angew. Chem. Int. Ed. 2022; 61: e202114550
  • 17 Roth D, Stirn J, Stephan D, Greb L. J. Am. Chem. Soc. 2021; 143: 15845
    • 18a Zhao Y, Truhlar DG. Theor. Chem. Acc. 2008; 120: 215
    • 18b Böhrer H, Trapp N, Himmel D, Schleep M, Krossing I. Dalton Trans. 2015; 44: 7489
    • 18c Greb L. Chem. Eur. J. 2018; 24: 17881