4 FLP-Mediated C–H-Activation
163
39. Hatakeyama T, Hashimoto S, Seki S, Nakamura M (2011) Synthesis of BN-Fused Polycyclic Aromatics via Tandem Intramolecular Electrophilic Arene Borylation. J Am Chem Soc
133:18614–18617. https://doi.org/10.1021/ja208950c
40. Lepeltier M, Lukoyanova O, Jacobson A, Jeeva S, Perepichka DF (2010) New AzaborineThiophene Heteroacenes. Chem Commun 46:7007–7009. https://doi.org/10.1039/c0cc01963a
41. Agou T, Kobayashi J, Kawashima T (2006) Syntheses, Structure, and Optical Properties of
Ladder-Type Fused Azaborines. Org Lett 8:2241–2244. https://doi.org/10.1021/ol060539n
42. Campbell PG, Marwitz AJV, Liu SY (2012) Recent Advances in Azaborine Chemistry. Angew
Chemie - Int Ed 51:6074–6092. https://doi.org/10.1002/anie.201200063
43. Taniguchi T, Yamaguchi S (2010) A Study of 1,2-Dihydro-1,2-azaborine in a π-Conjugated
System. Organometallics 29:5732–5735. https://doi.org/10.1021/om100408m
44. Qiang P, Sun Z, Wan M, Wang X, Thiruvengadam P, Bingi C, Wei W, Zhu W, Wu D, Zhang
F (2019) Successive Annulation to Fully Zigzag-Edged Polycyclic Heteroaromatic Hydrocarbons with Strong Blue-Green Electroluminescence. Org Lett 21:4575–4579. https://doi.org/
10.1021/acs.orglett.9b01487
45. Geim AK, Novoselov KS (2007) The Rise of Graphene. Nat Mater 6:183–191. https://doi.org/
10.1038/nmat1849
46. Wang XY, Wang JY, Pei J (2015) BN Heterosuperbenzenes: Synthesis and Properties. Chem
Eur J 21:3528–3539. https://doi.org/10.1002/chem.201405627
47. Sivaev IB, Bregadze VI (2014) Lewis Acidity of Boron Compounds. Coord Chem Rev 270–
271:75–88. https://doi.org/10.1016/j.ccr.2013.10.017
48. Parks DJ, Piers WE (1996) Tris(pentafluorophenyl)boron-Catalyzed Hydrosilation of Aromatic
Aldehydes, Ketones, and Esters. J Am Chem Soc 118:9440–9441. https://doi.org/10.1021/ja9
61536g
49. Rendler S, Oestreich M (2008) Conclusive Evidence for an S N 2-Si Mechanism in the
B(C 6 F 5 ) 3 -Catalyzed Hydrosilylation of Carbonyl Compounds: Implications for the Related
Hydrogenation. Angew Chem Int Ed 47:5997–6000. https://doi.org/10.1002/anie.200801675
50. De Vries TS, Prokofjevs A, Harvey JN, Vedejs E (2009) Superelectrophilic Intermediates in
Nitrogen-Directed Aromatic Borylation. J Am Chem Soc 131:14679–14687. https://doi.org/
10.1021/ja905369n
51. Prokofjevs A, Jermaks J, Borovika A, Kampf JW, Vedejs E (2013) Electrophilic C-H Borylation
and Related Reactions of B-H Boron Cations. Organometallics 32:6701–6711. https://doi.org/
10.1021/om400651p
52. Yin Q, Klare HFT, Oestreich M (2017) Catalytic Friedel-Crafts C-H Borylation of ElectronRich Arenes: Dramatic Rate Acceleration by Added Alkenes. Angew Chem Int Ed 56:3712–
3717. https://doi.org/10.1002/anie.201611536
53. Kitani F, Takita R, Imahori T, Uchiyama M (2017) Catalytic Aromatic Borylation via in situGenerated Borenium Species. Heterocycles 95:158–166. https://doi.org/10.3987/COM-16S(S)43
54. Gribble GW, Lord PD, Skotnicki J, Dietz SE, Eaton JT, Johnson J (1974) Reactions of Sodium
Borohydride in Acidic Media. I. Reduction of Indoles and Alkylation of Aromatic Amines
with Carboxylic Acids. J Am Chem Soc 96:7812–7814. https://doi.org/10.1021/ja00832a035
55. Jayaraman A, Powell-Davies H, Fontaine F-G (2019) Revisiting the Reduction of Indoles by
Hydroboranes: A Combined Experimental and Computational Study. Tetrahedron 75:2118–
2127. https://doi.org/10.1016/j.tet.2019.02.048
56. Wakamiya A, Yamaguchi S (2015) Designs of Functional π-Electron Materials Based on the
Characteristic Features of Boron. Bull Chem Soc Jpn 88:1357–1377. https://doi.org/10.1246/
bcsj.20150151
57. Maier AFG, Tussing S, Schneider T, Flörke U, Qu, Z-W, Grimme S, Paradies J (2016) Frustrated
Lewis Pair Catalyzed Dehydrogenative Oxidation of Indolines and Other Heterocycles. Angew
Chem Int Ed 55:12219–12223. https://doi.org/10.1002/anie.201606426
58. Zhang Q, Qin S, Yin Y, Hu J, Zhang H (2018) Boron(III)-Catalyzed C 2 -Selective C−H Borylation of Heteroarenes. Angew Chem Int Ed 57:14891–14895. https://doi.org/10.1002/anie.
201808590
163
39. Hatakeyama T, Hashimoto S, Seki S, Nakamura M (2011) Synthesis of BN-Fused Polycyclic Aromatics via Tandem Intramolecular Electrophilic Arene Borylation. J Am Chem Soc
133:18614–18617. https://doi.org/10.1021/ja208950c
40. Lepeltier M, Lukoyanova O, Jacobson A, Jeeva S, Perepichka DF (2010) New AzaborineThiophene Heteroacenes. Chem Commun 46:7007–7009. https://doi.org/10.1039/c0cc01963a
41. Agou T, Kobayashi J, Kawashima T (2006) Syntheses, Structure, and Optical Properties of
Ladder-Type Fused Azaborines. Org Lett 8:2241–2244. https://doi.org/10.1021/ol060539n
42. Campbell PG, Marwitz AJV, Liu SY (2012) Recent Advances in Azaborine Chemistry. Angew
Chemie - Int Ed 51:6074–6092. https://doi.org/10.1002/anie.201200063
43. Taniguchi T, Yamaguchi S (2010) A Study of 1,2-Dihydro-1,2-azaborine in a π-Conjugated
System. Organometallics 29:5732–5735. https://doi.org/10.1021/om100408m
44. Qiang P, Sun Z, Wan M, Wang X, Thiruvengadam P, Bingi C, Wei W, Zhu W, Wu D, Zhang
F (2019) Successive Annulation to Fully Zigzag-Edged Polycyclic Heteroaromatic Hydrocarbons with Strong Blue-Green Electroluminescence. Org Lett 21:4575–4579. https://doi.org/
10.1021/acs.orglett.9b01487
45. Geim AK, Novoselov KS (2007) The Rise of Graphene. Nat Mater 6:183–191. https://doi.org/
10.1038/nmat1849
46. Wang XY, Wang JY, Pei J (2015) BN Heterosuperbenzenes: Synthesis and Properties. Chem
Eur J 21:3528–3539. https://doi.org/10.1002/chem.201405627
47. Sivaev IB, Bregadze VI (2014) Lewis Acidity of Boron Compounds. Coord Chem Rev 270–
271:75–88. https://doi.org/10.1016/j.ccr.2013.10.017
48. Parks DJ, Piers WE (1996) Tris(pentafluorophenyl)boron-Catalyzed Hydrosilation of Aromatic
Aldehydes, Ketones, and Esters. J Am Chem Soc 118:9440–9441. https://doi.org/10.1021/ja9
61536g
49. Rendler S, Oestreich M (2008) Conclusive Evidence for an S N 2-Si Mechanism in the
B(C 6 F 5 ) 3 -Catalyzed Hydrosilylation of Carbonyl Compounds: Implications for the Related
Hydrogenation. Angew Chem Int Ed 47:5997–6000. https://doi.org/10.1002/anie.200801675
50. De Vries TS, Prokofjevs A, Harvey JN, Vedejs E (2009) Superelectrophilic Intermediates in
Nitrogen-Directed Aromatic Borylation. J Am Chem Soc 131:14679–14687. https://doi.org/
10.1021/ja905369n
51. Prokofjevs A, Jermaks J, Borovika A, Kampf JW, Vedejs E (2013) Electrophilic C-H Borylation
and Related Reactions of B-H Boron Cations. Organometallics 32:6701–6711. https://doi.org/
10.1021/om400651p
52. Yin Q, Klare HFT, Oestreich M (2017) Catalytic Friedel-Crafts C-H Borylation of ElectronRich Arenes: Dramatic Rate Acceleration by Added Alkenes. Angew Chem Int Ed 56:3712–
3717. https://doi.org/10.1002/anie.201611536
53. Kitani F, Takita R, Imahori T, Uchiyama M (2017) Catalytic Aromatic Borylation via in situGenerated Borenium Species. Heterocycles 95:158–166. https://doi.org/10.3987/COM-16S(S)43
54. Gribble GW, Lord PD, Skotnicki J, Dietz SE, Eaton JT, Johnson J (1974) Reactions of Sodium
Borohydride in Acidic Media. I. Reduction of Indoles and Alkylation of Aromatic Amines
with Carboxylic Acids. J Am Chem Soc 96:7812–7814. https://doi.org/10.1021/ja00832a035
55. Jayaraman A, Powell-Davies H, Fontaine F-G (2019) Revisiting the Reduction of Indoles by
Hydroboranes: A Combined Experimental and Computational Study. Tetrahedron 75:2118–
2127. https://doi.org/10.1016/j.tet.2019.02.048
56. Wakamiya A, Yamaguchi S (2015) Designs of Functional π-Electron Materials Based on the
Characteristic Features of Boron. Bull Chem Soc Jpn 88:1357–1377. https://doi.org/10.1246/
bcsj.20150151
57. Maier AFG, Tussing S, Schneider T, Flörke U, Qu, Z-W, Grimme S, Paradies J (2016) Frustrated
Lewis Pair Catalyzed Dehydrogenative Oxidation of Indolines and Other Heterocycles. Angew
Chem Int Ed 55:12219–12223. https://doi.org/10.1002/anie.201606426
58. Zhang Q, Qin S, Yin Y, Hu J, Zhang H (2018) Boron(III)-Catalyzed C 2 -Selective C−H Borylation of Heteroarenes. Angew Chem Int Ed 57:14891–14895. https://doi.org/10.1002/anie.
201808590