1 Frustrated Lewis Pair Catalysis: An Introduction
27
123. Chan JZ, Yao W, Hastings BT, Lok CK, Wasa M (2016) Direct Mannich-Type Reactions Promoted by Frustrated Lewis Acid/Brønsted Base Catalysts. Angew Chem Int Ed
55(44):13877–13881. https://doi.org/10.1002/anie.201608583
124. Pérez M, Mahdi T, Hounjet LJ, Stephan DW (2015) Electrophilic Phosphonium Cations
(EPCs) Catalyzed Hydroarylation and Hydrosulfuration of Olefins. Chem Commun
51:11301–11304. https://doi.org/10.1039/C5CC03572D
125. LaFortune JHW, Bayne JM, Johnstone TC, Fan L, Stephan DW (2017) Catalytic Double
Hydroarylation of Alkynes to 9,9-Disubstituted 9,10-Dihydroacridine Derivatives by an Electrophilic Phenoxyphosphonium Dication. Chem Commun 53:13312–13315. https://doi.org/
10.1039/C7CC08037A
126. Guo J, Cheong O, Bamford KL, Zhou J, Stephan DW (2020) Frustrated Lewis Pair-Catalyzed
Double Hydroarylation of Alkynes with N-Substituted Pyrroles. Chem Commun 56:18551858. https://doi.org/10.1039/C9CC08654D
127. Dureen MA, Stephan DW (2009) Terminal Alkyne Activation by Frustrated and Classical
Lewis Acid/Phosphine Pairs. J Am Chem Soc 131(24):8396–8398. https://doi.org/10.1021/
ja903650w
128. Legare MA, Courtemanche MA, Rochette E, Fontaine FG (2015) Metal-Free Catalytic C-H
Bond Activation and Borylation of Heteroarenes. Science 349(6247):513–516. https://doi.
org/10.1126/science.aab3591
129. Legare MA, Rochette E, Legare Lavergne J, Bouchard N, Fontaine FG (2016) Bench-Stable
Frustrated Lewis Pair Chemistry: Fluoroborate Salts as Precatalysts for the C-H Borylation
of Heteroarenes. Chem Commun 52(31):5387–5390. https://doi.org/10.1039/c6cc01267a
130. Chernichenko K, Lindqvist M, Kotai B, Nieger M, Sorochkina K, Papai I, Repo T
(2016) Metal-Free sp 2 -C-H Borylation as a Common Reactivity Pattern of Frustrated 2Aminophenylboranes. J Am Chem Soc 138(14):4860–4868. https://doi.org/10.1021/jacs.
6b00819
131. Legare Lavergne J, Jayaraman A, Misal Castro LC, Rochette E, Fontaine F-G (2017) MetalFree Borylation of Heteroarenes Using Ambiphilic Aminoboranes: On the Importance of
Sterics in Frustrated Lewis Pair C-H Bond Activation. J Am Chem Soc 139(41):14714–14723.
https://doi.org/10.1021/jacs.7b08143
132. Jayaraman A, Misal Castro LC, Desrosiers V, Fontaine FG (2018) Metal-Free Borylative Dearomatization of Indoles: Exploring the Divergent Reactivity of Aminoborane C-H
Borylation Catalysts. Chem Sci 9(22):5057–5063. https://doi.org/10.1039/c8sc01093e
133. Xu T, Chen EY (2014) Probing Site Cooperativity of Frustrated Phosphine/Borane Lewis
Pairs by a Polymerization Study. J Am Chem Soc 136(5):1774–1777. https://doi.org/10.
1021/ja412445n
134. Zhang YT, Miyake GM, John MG, Falivene L, Caporaso L, Cavallo L, Chen EYX (2012)
Lewis Pair Polymerization by Classical and Frustrated Lewis Pairs: Acid, Base and Monomer
Scope and Polymerization Mechanism. Dalton Trans 41(30):9119–9134. https://doi.org/10.
1039/C2dt30427a
135. Zhang YT, Miyake GM, Chen EYX (2010) Alane-Based Classical and Frustrated Lewis Pairs
in Polymer Synthesis: Rapid Polymerization of MMA and Naturally Renewable Methylene
Butyrolactones into High-Molecular-Weight Polymers. Angew Chem Int Ed 49(52):10158–
10162. https://doi.org/10.1002/anie.201005534
136. He JH, Zhang YT, Chen EYX (2014) Synthesis of Pyridine- and 2-Oxazoline-Functionalized
Vinyl Polymers by Alane-Based Frustrated Lewis Pairs. Synlett 25(11):1534–1538. https://
doi.org/10.1055/s-0033-1341248
137. Holtrichter-Rossmann T, Isermann J, Rosener C, Cramer B, Daniliuc CG, Kosters J, Letzel
M, Wurthwein EU, Uhl W (2013) An Aluminum-Nitrogen Based Lewis Pair as an Effective
Catalyst for the Oligomerization of Cyanamides: Formation of Acyclic C-N Oligomers Instead
of Thermodynamically Favored Cyclic Aromatic Trimers. Angew Chem Int Ed 52(28):7135–
7138. https://doi.org/10.1002/anie.201301970
138. Sajid M, Stute A, Cardenas AJP, Culotta BJ, Hepperle JAM, Warren TH, Schirmer B, Grimme
S, Studer A, Daniliuc CG, Frohlich R, Petersen JL, Kehr G, Erker G (2012) N,N-Addition
27
123. Chan JZ, Yao W, Hastings BT, Lok CK, Wasa M (2016) Direct Mannich-Type Reactions Promoted by Frustrated Lewis Acid/Brønsted Base Catalysts. Angew Chem Int Ed
55(44):13877–13881. https://doi.org/10.1002/anie.201608583
124. Pérez M, Mahdi T, Hounjet LJ, Stephan DW (2015) Electrophilic Phosphonium Cations
(EPCs) Catalyzed Hydroarylation and Hydrosulfuration of Olefins. Chem Commun
51:11301–11304. https://doi.org/10.1039/C5CC03572D
125. LaFortune JHW, Bayne JM, Johnstone TC, Fan L, Stephan DW (2017) Catalytic Double
Hydroarylation of Alkynes to 9,9-Disubstituted 9,10-Dihydroacridine Derivatives by an Electrophilic Phenoxyphosphonium Dication. Chem Commun 53:13312–13315. https://doi.org/
10.1039/C7CC08037A
126. Guo J, Cheong O, Bamford KL, Zhou J, Stephan DW (2020) Frustrated Lewis Pair-Catalyzed
Double Hydroarylation of Alkynes with N-Substituted Pyrroles. Chem Commun 56:18551858. https://doi.org/10.1039/C9CC08654D
127. Dureen MA, Stephan DW (2009) Terminal Alkyne Activation by Frustrated and Classical
Lewis Acid/Phosphine Pairs. J Am Chem Soc 131(24):8396–8398. https://doi.org/10.1021/
ja903650w
128. Legare MA, Courtemanche MA, Rochette E, Fontaine FG (2015) Metal-Free Catalytic C-H
Bond Activation and Borylation of Heteroarenes. Science 349(6247):513–516. https://doi.
org/10.1126/science.aab3591
129. Legare MA, Rochette E, Legare Lavergne J, Bouchard N, Fontaine FG (2016) Bench-Stable
Frustrated Lewis Pair Chemistry: Fluoroborate Salts as Precatalysts for the C-H Borylation
of Heteroarenes. Chem Commun 52(31):5387–5390. https://doi.org/10.1039/c6cc01267a
130. Chernichenko K, Lindqvist M, Kotai B, Nieger M, Sorochkina K, Papai I, Repo T
(2016) Metal-Free sp 2 -C-H Borylation as a Common Reactivity Pattern of Frustrated 2Aminophenylboranes. J Am Chem Soc 138(14):4860–4868. https://doi.org/10.1021/jacs.
6b00819
131. Legare Lavergne J, Jayaraman A, Misal Castro LC, Rochette E, Fontaine F-G (2017) MetalFree Borylation of Heteroarenes Using Ambiphilic Aminoboranes: On the Importance of
Sterics in Frustrated Lewis Pair C-H Bond Activation. J Am Chem Soc 139(41):14714–14723.
https://doi.org/10.1021/jacs.7b08143
132. Jayaraman A, Misal Castro LC, Desrosiers V, Fontaine FG (2018) Metal-Free Borylative Dearomatization of Indoles: Exploring the Divergent Reactivity of Aminoborane C-H
Borylation Catalysts. Chem Sci 9(22):5057–5063. https://doi.org/10.1039/c8sc01093e
133. Xu T, Chen EY (2014) Probing Site Cooperativity of Frustrated Phosphine/Borane Lewis
Pairs by a Polymerization Study. J Am Chem Soc 136(5):1774–1777. https://doi.org/10.
1021/ja412445n
134. Zhang YT, Miyake GM, John MG, Falivene L, Caporaso L, Cavallo L, Chen EYX (2012)
Lewis Pair Polymerization by Classical and Frustrated Lewis Pairs: Acid, Base and Monomer
Scope and Polymerization Mechanism. Dalton Trans 41(30):9119–9134. https://doi.org/10.
1039/C2dt30427a
135. Zhang YT, Miyake GM, Chen EYX (2010) Alane-Based Classical and Frustrated Lewis Pairs
in Polymer Synthesis: Rapid Polymerization of MMA and Naturally Renewable Methylene
Butyrolactones into High-Molecular-Weight Polymers. Angew Chem Int Ed 49(52):10158–
10162. https://doi.org/10.1002/anie.201005534
136. He JH, Zhang YT, Chen EYX (2014) Synthesis of Pyridine- and 2-Oxazoline-Functionalized
Vinyl Polymers by Alane-Based Frustrated Lewis Pairs. Synlett 25(11):1534–1538. https://
doi.org/10.1055/s-0033-1341248
137. Holtrichter-Rossmann T, Isermann J, Rosener C, Cramer B, Daniliuc CG, Kosters J, Letzel
M, Wurthwein EU, Uhl W (2013) An Aluminum-Nitrogen Based Lewis Pair as an Effective
Catalyst for the Oligomerization of Cyanamides: Formation of Acyclic C-N Oligomers Instead
of Thermodynamically Favored Cyclic Aromatic Trimers. Angew Chem Int Ed 52(28):7135–
7138. https://doi.org/10.1002/anie.201301970
138. Sajid M, Stute A, Cardenas AJP, Culotta BJ, Hepperle JAM, Warren TH, Schirmer B, Grimme
S, Studer A, Daniliuc CG, Frohlich R, Petersen JL, Kehr G, Erker G (2012) N,N-Addition