164
Y. Soltani and F.-G. Fontaine
59. Baker RT, Nguyen P, Marder TB, Westcott SA (1995) Transition Metal Catalyzed Diboration
of Vinylarenes. Angew Chem Int Ed 34:1336–1338. https://doi.org/10.1002/anie.199513361
60. Pubill-Ulldemolins C, Bonet A, Bo C, Gulyás H, Fernández E (2012) Activation of Diboron
Reagents with Brønsted Bases and Alcohols: An Experimental and Theoretical Perspective of
the Organocatalytic Boron Conjugate Addition Reaction. Chem Eur J 18:1121–1126. https://
doi.org/10.1002/chem.201102209
61. Sanz X, Lee GM, Pubill-Ulldemolins C, Bonet A, Gulyás H, Westcott SA, Bo C, Fernández
E (2013) Metal-Free Borylative Ring-Opening of Vinyl Epoxides and Aziridines. Org Biomol
Chem 11:7004–7010. https://doi.org/10.1039/c3ob41328d
62. Furukawa S, Kobayashi J, Kawashima T (2009) Development of a Sila-Friedel-Crafts Reaction
and Its Application to the Synthesis of Dibenzosilole Derivatives. J Am Chem Soc 131:14192–
14193. https://doi.org/10.1021/ja906566r
63. Furukawa S, Kobayashi J, Kawashima T (2010) Application of the Sila-Friedel-Crafts Reaction
to the Synthesis of π-Extended Silole Derivatives and their Properties. Dalton Trans 39:9329–
9336. https://doi.org/10.1039/c0dt00136h
64. Curless LD, Ingleson MJ (2014) B(C 6 F 5 ) 3 - Catalyzed Synthesis of Benzofused-Siloles.
Organometallics 33:7241–7246. https://doi.org/10.1021/om501033p
65. Curless LD, Clark ER, Dunsford JJ, Ingleson MJ (2014) E-H (E = R 3 Si or H) Bond Activation by B(C 6 F 5 ) 3 and Heteroarenes; Competitive Dehydrosilylation, Hydrosilylation and
Hydrogenation. Chem Commun 50:5270–5272. https://doi.org/10.1039/c3cc47372d
66. Ma Y, Wang B, Zhang L, Hou Z (2016) Boron-Catalyzed Aromatic C−H Bond Silylation with
Hydrosilanes. J Am Chem Soc 138:3663–3666. https://doi.org/10.1021/jacs.6b01349
67. Han Y, Zhang S, He J, Zhang Y (2018) Switchable C-H Silylation of Indoles Catalyzed by
a Thermally Induced Frustrated Lewis Pair. ACS Catal 8:8765–8773. https://doi.org/10.1021/
acscatal.8b01847
68. Dureen MA, Stephan DW (2009) Terminal Alkyne Activation by Frustrated and Classical
Lewis Acid/Phosphine Pairs. J Am Chem Soc 131:8396–8397. https://doi.org/10.1021/ja9
03650w
69. Moemming CM, Froemel S, Kehr G, Fröhlich R, Grimme S, Erker G (2009) Reactions of an
Intramolecular Frustrated Lewis Pair with Unsaturated Substrates: Evidence for a Concerted
Olefin Addition Reaction. J Am Chem Soc 131:12280–12289. https://doi.org/10.1021/ja9
03511s
70. Jiang C, Blacque O, Berke H (2010) Activation of Terminal Alkynes by Frustrated Lewis Pairs.
Organometallics 29:125–133. https://doi.org/10.1021/om9008636
71. Menard G, Stephan DW (2012) C-H Activation of Isobutylene Using Frustrated Lewis Pairs:
Aluminum and Boron sigma-Allyl Complexes. Angew Chem Int Ed 51:4409–4412. https://
doi.org/10.1002/anie.201200328
72. Voss T, Mahdi T, Otten E, Fröhlich R, Kehr G, Stephan DW, Erker G (2012) Frustrated
Lewis Pair Behavior of Intermolecular Amine/B(C 6 F 5 ) 3 Pairs. Organometallics 31:2367–2378.
https://doi.org/10.1021/om300017u
73. Iashin V, Chernichenko K, Pápai I, Repo T (2016) Atom-Efficient Synthesis of Alkynylfluoroborates Using BF 3 -Based Frustrated Lewis Pairs. Angew Chem Int Ed 55:14146–14150.
https://doi.org/10.1002/anie.201608520
74. Chernichenko K, Madarász Á, Pápai I, Nieger M, Leskelä M, Repo T (2013) A FrustratedLewis-Pair Approach to Catalytic Reduction of Alkynes to cis-Alkenes. Nat Chem 5:718–
723. https://doi.org/10.1038/nchem.1693
75. Lu G, Zhao L, Li H, Huang F, Wang Z-X (2010) Reversible Heterolytic Methane Activation of
Metal-Free Closed-Shell Molecules: A Computational Proof-of-Principle Study. Eur J Inorg
Chem 2254–2260. https://doi.org/10.1002/ejic.201000242
76. Frömel S, Daniliuc CG, Bannwarth C, Grimme S, Bussmann K, Kehr G, Erker G (2016) Indirect
Synthesis of a Pair of Formal Methane Activation Products at a Phosphane/Borane Frustrated
Lewis Pair. Dalton Trans 45:19230–19233. https://doi.org/10.1039/c6dt04206f
77. Rochette É, Courtemanche MA, Fontaine F-G (2017) Frustrated Lewis Pair Mediated Csp 3 −H
Activation. Chem Eur J 23:3567–3571. https://doi.org/10.1002/chem.201700390
Y. Soltani and F.-G. Fontaine
59. Baker RT, Nguyen P, Marder TB, Westcott SA (1995) Transition Metal Catalyzed Diboration
of Vinylarenes. Angew Chem Int Ed 34:1336–1338. https://doi.org/10.1002/anie.199513361
60. Pubill-Ulldemolins C, Bonet A, Bo C, Gulyás H, Fernández E (2012) Activation of Diboron
Reagents with Brønsted Bases and Alcohols: An Experimental and Theoretical Perspective of
the Organocatalytic Boron Conjugate Addition Reaction. Chem Eur J 18:1121–1126. https://
doi.org/10.1002/chem.201102209
61. Sanz X, Lee GM, Pubill-Ulldemolins C, Bonet A, Gulyás H, Westcott SA, Bo C, Fernández
E (2013) Metal-Free Borylative Ring-Opening of Vinyl Epoxides and Aziridines. Org Biomol
Chem 11:7004–7010. https://doi.org/10.1039/c3ob41328d
62. Furukawa S, Kobayashi J, Kawashima T (2009) Development of a Sila-Friedel-Crafts Reaction
and Its Application to the Synthesis of Dibenzosilole Derivatives. J Am Chem Soc 131:14192–
14193. https://doi.org/10.1021/ja906566r
63. Furukawa S, Kobayashi J, Kawashima T (2010) Application of the Sila-Friedel-Crafts Reaction
to the Synthesis of π-Extended Silole Derivatives and their Properties. Dalton Trans 39:9329–
9336. https://doi.org/10.1039/c0dt00136h
64. Curless LD, Ingleson MJ (2014) B(C 6 F 5 ) 3 - Catalyzed Synthesis of Benzofused-Siloles.
Organometallics 33:7241–7246. https://doi.org/10.1021/om501033p
65. Curless LD, Clark ER, Dunsford JJ, Ingleson MJ (2014) E-H (E = R 3 Si or H) Bond Activation by B(C 6 F 5 ) 3 and Heteroarenes; Competitive Dehydrosilylation, Hydrosilylation and
Hydrogenation. Chem Commun 50:5270–5272. https://doi.org/10.1039/c3cc47372d
66. Ma Y, Wang B, Zhang L, Hou Z (2016) Boron-Catalyzed Aromatic C−H Bond Silylation with
Hydrosilanes. J Am Chem Soc 138:3663–3666. https://doi.org/10.1021/jacs.6b01349
67. Han Y, Zhang S, He J, Zhang Y (2018) Switchable C-H Silylation of Indoles Catalyzed by
a Thermally Induced Frustrated Lewis Pair. ACS Catal 8:8765–8773. https://doi.org/10.1021/
acscatal.8b01847
68. Dureen MA, Stephan DW (2009) Terminal Alkyne Activation by Frustrated and Classical
Lewis Acid/Phosphine Pairs. J Am Chem Soc 131:8396–8397. https://doi.org/10.1021/ja9
03650w
69. Moemming CM, Froemel S, Kehr G, Fröhlich R, Grimme S, Erker G (2009) Reactions of an
Intramolecular Frustrated Lewis Pair with Unsaturated Substrates: Evidence for a Concerted
Olefin Addition Reaction. J Am Chem Soc 131:12280–12289. https://doi.org/10.1021/ja9
03511s
70. Jiang C, Blacque O, Berke H (2010) Activation of Terminal Alkynes by Frustrated Lewis Pairs.
Organometallics 29:125–133. https://doi.org/10.1021/om9008636
71. Menard G, Stephan DW (2012) C-H Activation of Isobutylene Using Frustrated Lewis Pairs:
Aluminum and Boron sigma-Allyl Complexes. Angew Chem Int Ed 51:4409–4412. https://
doi.org/10.1002/anie.201200328
72. Voss T, Mahdi T, Otten E, Fröhlich R, Kehr G, Stephan DW, Erker G (2012) Frustrated
Lewis Pair Behavior of Intermolecular Amine/B(C 6 F 5 ) 3 Pairs. Organometallics 31:2367–2378.
https://doi.org/10.1021/om300017u
73. Iashin V, Chernichenko K, Pápai I, Repo T (2016) Atom-Efficient Synthesis of Alkynylfluoroborates Using BF 3 -Based Frustrated Lewis Pairs. Angew Chem Int Ed 55:14146–14150.
https://doi.org/10.1002/anie.201608520
74. Chernichenko K, Madarász Á, Pápai I, Nieger M, Leskelä M, Repo T (2013) A FrustratedLewis-Pair Approach to Catalytic Reduction of Alkynes to cis-Alkenes. Nat Chem 5:718–
723. https://doi.org/10.1038/nchem.1693
75. Lu G, Zhao L, Li H, Huang F, Wang Z-X (2010) Reversible Heterolytic Methane Activation of
Metal-Free Closed-Shell Molecules: A Computational Proof-of-Principle Study. Eur J Inorg
Chem 2254–2260. https://doi.org/10.1002/ejic.201000242
76. Frömel S, Daniliuc CG, Bannwarth C, Grimme S, Bussmann K, Kehr G, Erker G (2016) Indirect
Synthesis of a Pair of Formal Methane Activation Products at a Phosphane/Borane Frustrated
Lewis Pair. Dalton Trans 45:19230–19233. https://doi.org/10.1039/c6dt04206f
77. Rochette É, Courtemanche MA, Fontaine F-G (2017) Frustrated Lewis Pair Mediated Csp 3 −H
Activation. Chem Eur J 23:3567–3571. https://doi.org/10.1002/chem.201700390