Skip to main content
SpringerLink
Log in

Fundamental and Applied Properties of Borocations

  • Chapter
  • First Online:
Book cover Synthesis and Application of Organoboron Compounds

Part of the book series: Topics in Organometallic Chemistry ((TOPORGAN,volume 49))

Abstract

The past 5 years has witnessed considerable growth in the field of borocation chemistry with a multitude of new cations containing 2, 3 and 4 coordinate boron centres reported. Perhaps more significant has been the expansion in the synthetic utility of borocations as stoichiometric reagents and catalysts. It is these new applications of borocations that are the primary focus of this article which concentrates on reports from 2009 to the end of June 2014. The correlation between structure and reactivity in these recent studies will be emphasised to aid in the future design of new borocations for specific targeted outcomes.

This is a preview of subscription content, log in via an institution to check access.

Access this chapter

Log in via an institution
Chapter
USD 29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD 169.00
Price excludes VAT (USA)
  • Available as EPUB and PDF
  • Read on any device
  • Instant download
  • Own it forever
Hardcover Book
USD 219.99
Price excludes VAT (USA)
  • Durable hardcover edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Institutional subscriptions

Notes

  1. 1.

    A CCDC search (June 2014) revealed 21 structures with the formula [R2BL][OTf] where the B–O bond distance is consistent with a significant interaction between the triflate anion and boron.

Abbreviations

[NTf2]− :

Triflimide −N(SO2CF3)2

[OTf]− :

Triflate −OSO2CF3

BBN:

9-Borabicyclo[3.3.1]nonane

Cat:

Catecholato ([o-C6H4O2]2−)

CatS2 :

Thiocatecholato ([o-C6H4S2]2−)

CIA:

Chloride ion affinity

DABCO:

Diazabicyclo[2.2.2]octane

DIPP:

2,6-Disopropylbenzene

DOSY:

Diffusion-ordered NMR spectroscopy

FIA:

Fluoride ion affinity

FLP:

Frustrated Lewis pair

HIA:

Hydride ion affinity

KIE:

Kinetic isotope effect

Mes:

Mesityl (2,4,6-Me3-C6H2)

NHC:

N-Heterocyclic carbene

PCM:

Polarisation continuum model

Pin:

Pinacolato ([OC(Me)2C(Me)2O]2−)

SEAr:

Electrophilic aromatic substitution

X-DMAP:

N,N-Dimethylaminopyridine (x = 2 or 4)

References

  1. Koelle P, Nöth H (1985) Chem Rev 85:399

    CAS  Google Scholar 

  2. Piers WE, Bourke SC, Conroy KD (2005) Angew Chem Int Ed 44:5016

    CAS  Google Scholar 

  3. De Vries TS, Prokofjevs A, Vedejs E (2012) Chem Rev 116:4246

    Google Scholar 

  4. Bissinger P, Braunschweig H, Damme A, Dewhurst RD, Kraft K, Kramer T, Radacki K (2013) Chem Eur J 19:13402

    CAS  Google Scholar 

  5. Wade CR, Broomsgrove AEJ, Aldridge S, Gabbai FP (2010) Chem Rev 132:3958

    Google Scholar 

  6. Solomon SA, Del Grosso A, Clark ER, Bagutski V, McDouall JJW, Ingleson MJ (2012) Organometallics 31:1908

    CAS  Google Scholar 

  7. De Vries TS, Prokofjevs A, Harvey JN, Vedejs E (2009) J Am Chem Soc 131:14679

    Google Scholar 

  8. Corey EJ (2009) Angew Chem Int Ed 48:2100

    CAS  Google Scholar 

  9. Ryschkewitsch GE, Wiggins JW (1979) J Am Chem Soc 92:1790

    Google Scholar 

  10. Bagutski V, Del Grosso A, Ayuso Carrillo J, Cade IA, Helm MD, Lawson JR, Singleton PJ, Solomon SA, Marcelli T, Ingleson MJ (2013) J Am Chem Soc 135:474

    CAS  Google Scholar 

  11. Brahmi MM, Malacria M, Curran DP, Fensterbank L, Lacôte E (2013) Synlett 24:1260

    CAS  Google Scholar 

  12. Vedejs E, Nguyen T, Powell DR, Schrimpf MR (1996) Chem Commun 2721

    Google Scholar 

  13. Clark ER, Del Grosso A, Ingleson MJ (2013) Chem Eur J 19:2462

    CAS  Google Scholar 

  14. Bentivegna B, Mariani CI, Smith JR, Ma S, Rheingold AL, Brunker TJ (2014) Organometallics 33:2820

    CAS  Google Scholar 

  15. Saito M, Matsumoto K, Fujita M, Minoura M (2014) Heteroatom Chem 25:354–360

    CAS  Google Scholar 

  16. Reed CA (1998) Acc Chem Res 31:325

    CAS  Google Scholar 

  17. Del Grosso A, Muryn CA, Pritchard RG, Ingleson MJ (2010) Organometallics 29:241

    Google Scholar 

  18. Muthaiah S, Do DCH, Ganguly R, Vidovic D (2013) Organometallics 32:6718

    CAS  Google Scholar 

  19. McArthur D, Butts CP, Lindsay DM (2011) Chem Commun 47:6650

    CAS  Google Scholar 

  20. Litters S, Kaifer E, Enders M, Himmel HJ (2013) Nat Chem 5:1029

    CAS  Google Scholar 

  21. Prokofjevs A, Kampf JW, Solovyev A, Curran DP, Vedejs E (2013) J Am Chem Soc 135:15686

    CAS  Google Scholar 

  22. Hayashi Y, Segawa Y, Yamashita M, Nozaki K (2011) Chem Commun 47:5888

    CAS  Google Scholar 

  23. Wang Y, Abraham MY, Gillard RJ, Sexton DR, Wei P, Robinson GH (2013) Organometallics 32:6639

    CAS  Google Scholar 

  24. De Vries TS, Vedejs E (2007) Organometallics 26:3079

    Google Scholar 

  25. Del Grosso A, Helm MD, Solomon SA, Caras Quintero D, Ingleson MJ (2011) Chem Commun 47:12459

    Google Scholar 

  26. Reichardt C, Welton TE (2010) Solvents and solvent effects in organic chemistry, 4th edn. Wiley, Weinheim

    Google Scholar 

  27. Sivaev IB, Bregadze VI (2014) Coord Chem Rev 270:75

    Google Scholar 

  28. Krossing I, Raabe I (2004) Angew Chem Int Ed 43:2066

    CAS  Google Scholar 

  29. Beckett MA, Brassington DS, Coles SJ, Hursthouse MB (2000) Inorg Chem Commun 3:530

    CAS  Google Scholar 

  30. Childs RF, Mulholland DL, Nixon A (1982) Can J Chem 60:801

    CAS  Google Scholar 

  31. Bonnier C, Piers WE, Parvez M Sorensen, TS (2008) Chem Commun 4593

    Google Scholar 

  32. Chen J, Lalancette RA, Jäkle F (2013) Chem Commun 49:4893

    CAS  Google Scholar 

  33. Prokofjevs A (2012) DPhil Thesis, University of Michigan

    Google Scholar 

  34. Erker G, Stephan DW (eds) (2013) Frustrated Lewis pairs: uncovering and understanding. Springer, Berlin

    Google Scholar 

  35. Dureen MA, Lough A, Gilbert TM, Stephan DW (2008) Chem Commun 4303

    Google Scholar 

  36. Lata CJ, Crudden CM (2009) J Am Chem Soc 132:131

    Google Scholar 

  37. Del Grosso A, Singleton PJ, Muryn CA, Ingleson MJ (2011) Angew Chem Int Ed 50:2102

    Google Scholar 

  38. Ines B, Patil M, Carreras J, Goddard R, Thiel W, Alcarazo M (2011) Angew Chem Int Ed 50:8400

    CAS  Google Scholar 

  39. Chen WC, Lee CY, Lin BC, Hsu YC, Shen JS, Hsu CP, Yap GPA, Ong TG (2014) J Am Chem Soc 136:914

    CAS  Google Scholar 

  40. Farrell JM, Hatnean JA, Stephan DW (2012) J Am Chem Soc 134:15728

    CAS  Google Scholar 

  41. Erhardt S, Frenking G (2006) Chem Eur J 12:4620

    CAS  Google Scholar 

  42. Bessac F, Frenking G (2003) Inorg Chem 42:7990

    CAS  Google Scholar 

  43. Marwitz AJV, Jenkins JT, Zakharov LV, Liu SY (2010) Angew Chem Int Ed 49:7444

    CAS  Google Scholar 

  44. Denmark SE, Ueki Y (2013) Organometallics 32:6631

    CAS  Google Scholar 

  45. Solovyev A, Geib SJ, Lacôte E, Curran DP (2012) Organometallics 31:54

    CAS  Google Scholar 

  46. Genaev AM, Nagy SM, Salnikov GE, Shubin VG (2000) Chem Commun 1587

    Google Scholar 

  47. Hurd DT (1948) J Am Chem Soc 70:2053

    CAS  Google Scholar 

  48. Goldfuss B, Knochel P, Bromm LO, Knapp K (2000) Angew Chem Int Ed 39:4136

    CAS  Google Scholar 

  49. Prokofjevs A, Jermaks J, Borovika A, Kampf JW, Vedejs E (2013) Organometallics 32:6701

    CAS  Google Scholar 

  50. Ishida N, Moriya T, Goya T, Murakami M (2010) J Org Chem 75:8709

    CAS  Google Scholar 

  51. Niu L, Yang H, Wang R, Fu H (2012) Org Lett 14:2618

    CAS  Google Scholar 

  52. Zhao Z, Chang Z, He B, Chen B, Deng C, Lu P, Qiu H, Tang BZ (2013) Chem Eur J 19:11512

    CAS  Google Scholar 

  53. Cazorla C, De Vries TS, Vedejs E (2013) Org Lett 15:984

    CAS  Google Scholar 

  54. Chen J, Lalancette RA, Jäkle F (2013) Organometallics 32:5483

    Google Scholar 

  55. Hatakeyama T, Hashimoto S, Seki S, Nakamura M (2011) J Am Chem Soc 133:18614

    CAS  Google Scholar 

  56. Hatakeyama T, Hashimoto S, Oba T, Nakamura M (2012) J Am Chem Soc 134:19600

    CAS  Google Scholar 

  57. Prokofjevs A, Vedejs E (2011) J Am Chem Soc 133:20056

    CAS  Google Scholar 

  58. Bissinger P, Braunschweig H, Damme A, Dewhurst RD, Kupfer T, Radacki K, Wagner K (2011) J Am Chem Soc 133:19044

    CAS  Google Scholar 

  59. Mansaray HB, Rowe ADL, Phillips N, Niemeyer J, Kelly M, Addy DA, Bates JI, Aldridge S (2011) Chem Commun 47:12295

    CAS  Google Scholar 

  60. Bujwid ZJ, Gerrard W, Lappert MF (1959) Chem Ind 1091

    Google Scholar 

  61. Muetterties EL (1959) J Am Chem Soc 81:2597

    CAS  Google Scholar 

  62. Muetterties EL (1960) J Am Chem Soc 82:4163

    CAS  Google Scholar 

  63. Muetterties EL, Tebbe FN (1968) Inorg Chem 7:2663

    CAS  Google Scholar 

  64. Ingleson MJ (2012) Synlett 23:1411

    CAS  Google Scholar 

  65. Olah GA (1993) Angew Chem Int Ed 32:767

    Google Scholar 

  66. Reus C, Weidlich S, Bolte M, Lerner HW, Wagner M (2013) J Am Chem Soc 135:12892

    CAS  Google Scholar 

  67. Bregadze VI, Kosenko ID, Lobanova IA, Starikova ZA, Godovikov IA, Sivaev IB (2010) Organometallics 29:5366–5372

    CAS  Google Scholar 

  68. Kosenko ID, Lobanova IA, Godovikov IA, Starikova ZA, Sivaev IB (2012) J Organomet Chem 721:70

    Google Scholar 

  69. Zharov I, Havlas Z, Orendt AM, Barich DH, Grant DM, Fete MG, Michl J (2006) J Am Chem Soc 128:6089

    CAS  Google Scholar 

  70. Prokofjevs A, Kampf JW, Vedejs E (2011) Angew Chem Int Ed 50:2098

    CAS  Google Scholar 

  71. Del Grosso A, Clark ER, Montoute N, Ingleson MJ (2012) Chem Commun 48:7589

    Google Scholar 

  72. Mkhalid IAI, Barnard JH, Marder TB, Murphy JM, Hartwig JF (2010) Chem Rev 110:890

    CAS  Google Scholar 

  73. Stahl T, Muther K, Ohki Y, Tatsumi K, Oestreich M (2013) J Am Chem Soc 135:10978

    CAS  Google Scholar 

  74. Lawson JR, Clark ER, Cade IA, Solomon SA, Ingleson MJ (2013) Angew Chem Int Ed 52:7518

    CAS  Google Scholar 

  75. Scheideman M, Shapland P, Vedejs E (2003) J Am Chem Soc 125:10502

    CAS  Google Scholar 

  76. Clay JM, Vedejs E (2005) J Am Chem Soc 127:5766

    CAS  Google Scholar 

  77. Scheideman M, Wang G, Vedejs E (2008) J Am Chem Soc 130:8669

    CAS  Google Scholar 

  78. Prokofjevs A, Boussonnière A, Li L, Bonin H, Lacôte E, Curran DP, Vedejs E (2012) J Am Chem Soc 134:12281

    CAS  Google Scholar 

  79. Pan X, Boussonniere A, Curran DP (2013) J Am Chem Soc 135:14433

    CAS  Google Scholar 

  80. Boussonniere A, Pan X, Geib SJ, Curran DP (2013) Organometallics 32:7445

    CAS  Google Scholar 

  81. Wrackmeyer B (1995) Coord Chem Rev 145:125

    CAS  Google Scholar 

  82. Freitas LBO, Eisenberger P, Crudden CM (2013) Organometallics 32:6635

    Google Scholar 

  83. Lappert MF, Prokai B (1964) J Organomet Chem 1:384

    CAS  Google Scholar 

  84. Wrackmeyer B (1986) Polyhedron 5:1709

    CAS  Google Scholar 

  85. Yao ML, Reddy MS, Zeng W, Hall K, Walfish I, Kabalka GW (2009) J Org Chem 74:1385

    CAS  Google Scholar 

  86. Wang C, Uchiyama M (2012) Eur J Org Chem 6548

    Google Scholar 

  87. Cade IA, Ingleson MJ (2014) Chem Eur J 20:12874

    CAS  Google Scholar 

  88. Schafer W, Hellmann H (1967) Angew Chem Int Ed 6:518

    Google Scholar 

  89. Shoji Y, Tanaka N, Mikami K, Uchiyama M, Fukushima T (2014) Nat Chem 6:498

    CAS  Google Scholar 

  90. Reus C, Wagner M (2014) Nat Chem 6:466

    CAS  Google Scholar 

  91. Corey EJ (2002) Angew Chem Int Ed 41:1650

    CAS  Google Scholar 

  92. Sakata K, Fujimoto H (2013) J Org Chem 78:3095

    CAS  Google Scholar 

  93. Paddon-Row MN, Anderson CD, Houk KN (2009) J Org Chem 74:861

    CAS  Google Scholar 

  94. Payette JN, Yamamoto H (2007) J Am Chem Soc 129:9536

    CAS  Google Scholar 

  95. Payette JN, Yamamoto H (2009) Angew Chem Int Ed Engl 48:8060

    CAS  Google Scholar 

  96. Hall DG (2011) Boronic acids: preparation and applications in organic synthesis, medicine and materials, 2nd edn. Wiley-VCH, Weinheim

    Google Scholar 

  97. Olah GA, Aniszfeld R, Surya-Prakash GK, Williams RE, Lammertsma K, Guner OF (1988) J Am Chem Soc 110:7885

    CAS  Google Scholar 

  98. Clark ER, Ingleson MJ (2013) Organometallics 32:6712

    CAS  Google Scholar 

  99. Eisenberger P, Bailey AM, Crudden CM (2012) J Am Chem Soc 134:17384

    CAS  Google Scholar 

  100. Piers WE, Marwitz AJV, Mercier LG (2011) Inorg Chem 50:12252

    CAS  Google Scholar 

  101. Rendler S, Oestreich M (2008) Angew Chem Int Ed 47:5997

    CAS  Google Scholar 

  102. Wei P, Atwood DA (1998) Inorg Chem 37:4934

    CAS  Google Scholar 

  103. Hudnall TW, Chiu CW, Gabbai FP (2009) Acc Chem Res 42:388

    CAS  Google Scholar 

  104. Tsurumaki E, Hayashi S, Tham FS, Reed CA, Osuka A (2013) J Am Chem Soc 133:11956

    Google Scholar 

  105. Berger CJ, He G, Merten C, McDonald R, Ferguson MJ, Rivard E (2014) Inorg Chem 53:1475

    CAS  Google Scholar 

  106. Cui C, Jäkle F (2009) Chem Commun 2744

    Google Scholar 

  107. Cui C, Heilmann-Brohl J, Perucha AS, Thomson MD, Roskos HG, Wagner M, Jäkle F (2010) Macromolecules 43:5256

    CAS  Google Scholar 

  108. Wiggins KM, Hudnall TW, Tennyson AG, Bielawski CW (2011) J Mater Chem 21:8355

    CAS  Google Scholar 

  109. Ruther T, Huynh TD, Huang J, Hollenkamp AF, Salter EA, Wierzbicki A, Mattson K, Lewis AJHD (2010) Chem Mater 22:1038

    CAS  Google Scholar 

  110. Wang K, Zhang Y, Chand D, Parrish DA, Shreeve JM (2012) Chem Eur J 18:16931

    CAS  Google Scholar 

  111. Dorman SC, O’Brien RA, Lewis AT, Salter EA, Wierzbicki A, Hixon PW, Sykora RE, Mirjafari A, Davis JH (2011) Chem Commun 47:9072

    CAS  Google Scholar 

  112. Wood TK, Piers WE, Keay BA, Parvez M (2009) Chem Commun 5147

    Google Scholar 

  113. Mansell SM, Adams CJ, Bramham G, Haddow MF, Kaim W, Norman NC, McGrady JE, Russell CA, Udeen SJ (2010) Chem Commun 5070

    Google Scholar 

  114. Ruiz DA, Melaimi M, Bertrand G (2014) Chem Commun 50:7837

    CAS  Google Scholar 

  115. Kong L, Li Y, Ganguly R, Vidovic D, Kinjo R (2014) Angew Chem Int Ed 53:9280

    CAS  Google Scholar 

  116. Matsumoto T, Gabbai FP (2009) Organometallics 28:4252

    CAS  Google Scholar 

  117. Chiu CW, Gabbai FP (2008) Organometallics 27:1657

    CAS  Google Scholar 

  118. Braunschweig H, Damme A, Dewhurst RD, Kramer T, Kupfer T, Radacki K, Siedler E, Trumpp A, Wagner K, Werner C (2013) J Am Chem Soc 135:8702

    CAS  Google Scholar 

  119. Cade IA, Hill AF (2012) Organometallics 31:2112

    CAS  Google Scholar 

  120. Shen CT, Liu YH, Peng SM, Chiu CW (2013) Angew Chem Int Ed 52:13293

    CAS  Google Scholar 

  121. Focante F, Mercandelli P, Sironi A, Resconi L (2006) Coord Chem Rev 250:170

    CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. School of Chemistry, The University of Manchester, Chemistry Building-4.02 K, Manchester, M13 9PL, UK

    Michael J. Ingleson

Authors
  1. Michael J. Ingleson
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Michael J. Ingleson .

Editor information

Editors and Affiliations

  1. Universitat Rovira i Virgili Directora TECAT, Tarragona, Spain

    Elena Fernández

  2. Department of Chemistry, Centre for Sustainable Chemical Processes, Durham, United Kingdom

    Andrew Whiting

Rights and permissions

Reprints and permissions

Copyright information

© 2015 Springer International Publishing Switzerland

About this chapter

Cite this chapter

Ingleson, M.J. (2015). Fundamental and Applied Properties of Borocations. In: Fernández, E., Whiting, A. (eds) Synthesis and Application of Organoboron Compounds. Topics in Organometallic Chemistry, vol 49. Springer, Cham. https://doi.org/10.1007/978-3-319-13054-5_2

Download citation

Publish with us

Policies and ethics

Search

Navigation