Electrochemical properties and reactions of organoboron compounds

Current Opinion in Electrochemistry

Volumn 2, Issue 1, 2017, Pages 32-37

  Inagi, Shinsuke ^a   Fuchigami, Toshio ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 85033778421     PISSN: 24519103     EISSN: 24519111     Source Type: Journal    
DOI: 10.1016/j.coelec.2017.02.007     Document Type: Review

References (50)

1. Pelter, A., Smith, K., Brown, H.C., Borane Reagents. 1988, Academic Press, London.
2. Brown, H.C., Subba Rao, B.C., A new technique for the conversion of olefins into organoboranes and related alcohols. J Am Chem Soc 78 (1956), 5694–5695.
3. Brown, H.C., Phadke, A.S., Rangaishenvi, M.V., Ring enlargement of boracyclanes via sequential one-carbon homologation. The first synthesis of boracyalanes in the strained medium ring range. J Am Chem Soc 110 (1988), 6263–6264.
4. Miyaura, N., Suzuki, A., Palladium-catalyzed cross-coupling reactions of organoboron compounds. Chem Rev 95 (1995), 2457–2483.
5. Suzuki, A., Recent advances in the cross-coupling reactions of organoboron derivatives with organic electrophiles, 1995–1998. J Organomet Chem 576 (1999), 147–168.
6. Boron Science. New Technologies and Applications. Hosmane, N.S., (eds.) New Technologies and Applications, 2011, CRC Press, FL.
7. Grimes, R.N., Carboranes. 2nd ed., 2011, Academic Press, London.
8. π−π* conjugation. J Am Chem Soc 124 (2002), 8816–8817.
9. Solé, S., Gabbaï, F.P., A bidentate borane as colorimetric fluoride ion sensor. Chem Commun, 2004, 1284–1285.
10. Liu, X.Y., Bai, D.R., Wang, S., Charge-transfer emission in nonplanar three-coordinate organoboron compounds for fluorescent sensing of fluoride. Angew Chem Int Ed 45 (2006), 5475–5478.
11. Miyata, M., Chujo, Y., π-Conjugated organoboron polymer as an anion sensor. Polym J 34 (2002), 967–969.
12. Dusemund, C., Samankumara Sandanayake, K.R.A., Shikai, S., Selective fluoride recognition with ferroceneboronic acid. J Chem Soc Chem Commun, 1995, 333–334.
13. Nicoas, M.N., Fabre, B., Marchand, G., Simonet, J., New boronic-acid- and boronate-substituted aromatic compounds as precursors of fluoride-responsive conjugated polymer films. Eur J Org Chem, 2000, 1703–1710.
14. Ooyama, Y., Matsugasako, A., Oka, K., Nagano, T., Sumomogi, M., Komaguchi, K., Imae, I., Harima, Y., Fluorescence PET (photo-induced electron transfer) sensors for water based on anthracene-boronic acid ester. Chem Commun 47 (2011), 4448–4450.
15. Shinkai, S., Takeuchi, M., Molecular design of artificial sugar sensing systems. Trends Anal Chem 15 (1996), 188–194.
16. Miyahara, T., Kurihara, K., Electroconductive Langmuir−Blodgett films containing a carotenoid amphiphile for sugar recognition. J Am Chem Soc 126 (2004), 5684–5685.
17. Takahashi, S., Anzai, J., Phenylboronic acid monolayer-modified electrodes sensitive to sugars. Langmuir 21 (2005), 5102–5107.
18. Malkowsky, I.M., Rommel, C.E., Fröhlich, R., Griesbach, U., Pütter, H., Waldvogel, S.R., Novel template-directed anodic phenol-coupling reaction. Chem Eur J 17 (2006), 7482–7488.
19. Morris, J.H., Gysling, H.J., Reed, D., Electrochemistry of boron compounds. Chem Rev 85 (1985), 51–76.
20. Nepomnyashchii, A.B., Bard, A.J., Electrochemistry and electrogenerated chemiluminescence of BODIPY dyes. Acc Chem Res 45 (2012), 1844–1853.
21. Pintaric, C., Laza, C., Olivero, S., Dunach, E., Electrosynthesis of benzylboronic acids and esters. Tetrahedron Lett 45 (2004), 8031–8033.
22. Laza, C., Pintaric, C., Olivero, S., Dunach, E., Electrochemical reduction of polyhalogenated aryl derivatives in the presence of pinacolborane: electrosynthesis of fuctionalised arylvoronic esters. Electrochim Acta 50 (2005), 4897–4901.
23. Schäfer, H., Koch, D., Anodic oxidation of trihexylmethoxyborate in presence of butadiene. Angew Chem Int Ed 11 (1972), 48–49.
24. Taguchi, T., Itoh, M., Suzuki, A., Anodic oxidation of trialkylboranes. A new procedure of alkyl coupling reaction of organoboranes. Chem Lett, 1973, 719–722.
25. Taguchi, T., Takahashi, Y., Itoh, M., Suzuki, A., Anodic oxidation of trialkylboranes using graphite as the anode. Novel reaction of organoboranes proceeding through a carbonium ion mechanism. Chem Lett, 1974, 1021–1024.
26. Keating, J.T., Skell, P.S., Free carbonium ions in the anodic oxidations of alkanecarboxylates, alkaneboronates, and alkyl halides. J Org Chem 34 (1969), 1479–1480.
27. Humffray, A.A., Williams, L.F.G., Anodic oxidation of n-butylboronic acid. Chem Commun, 1965, 616.
28. Humffray, A.A., Williams, L.F.G., The anodic oxidation of boronic acids-I. n-Butaneboronic acid: product yields and comparison with pentanoic acid. Electrochim Acta 17 (1972), 401–408.
29. Williams, L.F.G., Humffray, A.A., The anodic oxidation of boronic acids-II. n-Butaneboronic acid: electrode kinetics. Electrochim Acta 17 (1972), 409–414.
30. Tanigawa, M., Kuriyama, Y., Inagi, S., Fuchigami, T., Electrochemical properties and reactions of sulfur-containing organoboron compounds. Electrochim Acta 199 (2016), 314–318.
31. Suzuki, J., Shida, N., Inagi, S., Fuchigami, T., Electrochemical properties and reactions of organoboronic acids in the presence of fluoride ions. Electroanalysis 28 (2016), 2797–2801.
32. Suzuki, J., Tanigawa, M., Inagi, S., Fuchigami, T., Electrochemical oxidation of organotrifluoroborate compounds. ChemElectroChem 3 (2016), 2078–2085.
33. Ohtsuka, K., Inagi, S., Fuchigami, T., Elecrochemical properties and reactions of oxygen-containing organotrifluoroborates and their boronic acid esters. ChemElectroChem 4 (2017), 183–187.
34. Ohtsuka, K., Inagi, S., Fuchigami, T., Electrochemical properties and reactions of organoboronic acid esters containing unsaturated bonds at their α-position. J Electrochem Soc 164 (2017), G23–G28.
35. Yoshida, J., Nokami, T., Suga, S., Organic Electrochemistry. Hammerich, O., Speiser, B., (eds.), 5th Ed, 2015, CRC Press, Boca Raton, FL Chapter 35.
36. Yoshida, J., Kataoka, K., Horcajada, R., Nagaki, A., Modern strategies in electroorganic synthesis. Chem Rev 108 (2008), 2265–2299.
37. Yasu, Y., Koike, T., Akita, M., Visible light-induced selective generation of radicals from organoborates by photoredox catalysis. Adv Synth Catal 354 (2012), 3414–3420.
38. Tellis, J.C., Primer, D.N., Molander, G.A., Single-electron transmetalation in organocoron cross coupling by photoredox/nickel dual catalysis. Science 345 (2014), 433–437.
39. Huang, H., Jia, K., Chen, Y., Hypervalent Iodinereagents enable chemoselective debromonative/decarboxylative alkenylation by photoredox catalysis. Angew Chem Int Ed 54 (2015), 1881–1884.
40. Huo, H., Harms, K., Meggers, E., Catalytic, enantioselective addition of alkyl radicals to alkenes via visible-light-activated photoredox catalysis with a chiral rhodium complex. J Am Chem Soc 138 (2016), 6936–6939.
41. Shundrin, L.A., Bardin, V.V., Frohn, H.-J., (Fluoroorgano)fluoroboranes and -borates. 11. The electrochemical oxidation of polyfluorophenyltrifluoroborate anions in acetonitrile. Z Anorg Allg Chem 630 (2004), 1253–1257.
42. Qi, H.-L., Chen, D.-S., Ye, J.-S., Huang, J.-M., Electrochemical technique and copper-promoted transformations: selective hydroxylation and amination of arylboronic acids. J Org Chem 78 (2013), 7482–7487.
43. Mitsudo, K., Shiraga, T., Kagen, D., Shi, D., Becker, J.Y., Tanaka, H., Pd/TEMPO-catalyzed electrooxidative synthesis of biaryls from arylboronic acids or esters. Tetrahedron 65 (2009), 8384–8388.
44. 2/p-benzoquinone-catalyzed anaerobic electrooxidative homocoupling of arylboronic acids, arylboronates and aryltrifluoroborates in DMF and/or water. Eur J Org Chem, 2008, 4567–4570.
45. DuPont, T.J., Mills, J.L., Arylborane anions. An electrochemical study. J Am Chem Soc 97 (1975), 6375–6382.
46. Shi, D.-Q., Gitkis, A., Becker, J.Y., Anodic carbon–boron bond cleavage through the intermediacy of electrogenerated bromonium ion. Electrochim Acta 53 (2007), 1824–1829.
47. Hosoi, K., Kuriyama, Y., Inagi, S., Fuchigami, T., Electrochemical hydroxylation of organoboron compounds. Chem Commun 46 (2010), 1284–1286.
48. 3 electride as a new electrode for superoxide ion generation and hydroxylation of an arylboronic acid. Electrochem Commun 17 (2012), 52–55.
49. Hosoi, K., Inagi, S., Kubo, T., Fuchigami, T., o-Carborane as an electron-transfer mediator in electrocatalytic reduction. Chem Commun 47 (2011), 8632–8634.
50. Inagi, S., Hosoi, K., Kubo, T., Shida, N., Fuchigami, T., o-Carborane-triphenylamine diad: studies on its acceptor-donor behavior toward dual redox mediator. Electrochemistry 81 (2013), 368–370.