162
Y. Soltani and F.-G. Fontaine
18. García-Cuadrado D, Braga AAC, Maseras F, Echavarren AM (2006) Proton Abstraction Mechanism for the Palladium-Catalyzed Intramolecular Arylation. J Am Chem Soc 128:1066–1067.
https://doi.org/10.1021/ja056165v
19. Lafrance M, Fagnou K (2006) Palladium-Catalyzed Benzene Arylation: Incorporation of
Catalytic Pivalic Acid as a Proton Shuttle and a Key Element in Catalyst Design. J Am Chem
Soc 128:16496–16497. https://doi.org/10.1021/ja067144j
20. Lafrance M, Rowley CN, Woo TK, Fagnou K (2006) Catalytic Intermolecular Direct Arylation
of Perfluorobenzenes. J Am Chem Soc 128:8754–8756. https://doi.org/10.1021/ja062509l
21. U. S. Food and Drug Administration/Center for Biologics Evaluation and Research, CDER
(2015) Guidance for Industry Q3D Elemental Impurities. Food Drug Adm 1–85
22. Usluer Ö, Abbas M, Wantz G, Vignau L, Hirsch L, Grana E, Brochon C, Cloutet E, Hadziioannou G (2014) Metal Residues in Semiconducting Polymers: Impact on the Performance
of Organic Electronic Devices. ACS Macro Lett 3:1134–1138. https://doi.org/10.1021/mz5
00590d
23. Welch GC, Juan RRS, Masuda JD, Stephan DW (2006) Reversible, Metal-Free Hydrogen
Activation. Science 314:1124–1126. https://doi.org/10.1126/science.1134230
24. Fontaine FG, Stephan DW (2017) On the Concept of Frustrated Lewis Pairs. Philos Trans R
Soc A Math Phys Eng Sci 375:1–8. https://doi.org/10.1098/rsta.2017.0004
25. Muetterties EL (1959) Synthesis of Aryldichloroboranes. J Am Chem Soc 81:2597–2597.
https://doi.org/10.1021/ja01519a079
26. Muetterties EL, Tebbe FN (1968) Dichloroboronation of Aromatic Hydrocarbons. Mechanistic
Aspects. Inorg Chem 7:2663–2664. https://doi.org/10.1021/ic50070a048
27. Muetterties EL (1967) The Chemistry of Boron and its Compounds. Wiley, New York
28. Muetterties EL (1960) Synthesis of Organoboranes. J Am Chem Soc 82:4163–4166. https://
doi.org/10.1021/ja01501a010
29. Bagutski V, Del Grosso A, Carrillo JA, Cade IA, Helm MD, Lawson JR, Singleton PJ, Solomon
SA, Marcelli T, Ingleson MJ (2013) Mechanistic Studies into Amine-Mediated Electrophilic
Arene Borylation and its Application in MIDA Boronate Synthesis. J Am Chem Soc 135:474–
487. https://doi.org/10.1021/ja3100963
30. Davis FA, Dewar MJS (1960) New Heteroaromatic Compounds. A Derivative of 10,9Borathiarophenanthrene. J Org Chem 25:3511–3515. https://doi.org/10.1021/ja01015a039
31. Genaev AM, Nagy SM, Salnikov GE, Shubin VG (2000) Intramolecular Borylation Reaction
Catalyzed by Lewis Acid: Preparation of 1H-2,1-Benzazaborole Derivatives. Chem Commun
1587–1588. https://doi.org/10.1039/B003999N
32. Ishida N, Moriya T, Goya T, Murakami M (2010) Synthesis of Pyridine-Borane Complexes
via Electrophilic Aromatic Borylation. J Org Chem 75:8709–8712. https://doi.org/10.1021/
jo101920p
33. Del Grosso A, Pritchard RG, Muryn CA., Ingleson MJ, (2010) Chelate Restrained Boron
Cations for Intermolecular Electrophilic Arene Borylation. Organometallics 29:241–249.
https://doi.org/10.1021/om900893g
34. Del Grosso A, Singleton PJ, Muryn CA, Ingleson MJ (2011) Pinacol Boronates by Direct
Arene Borylation with Borenium Cations. Angew Chem Int Ed 50:2102–2106. https://doi.
org/10.1002/anie.201006196
35. Solomon SA, Del Grosso A, Clark ER, Bagutski V, McDouall JJW, Ingleson MJ (2012) Reactivity of Lewis Acid Activated Diaza- and Dithiaboroles in Electrophilic Arene Borylation.
Organometallics 31:1908–1916. https://doi.org/10.1021/om201228e
36. Del Grosso A, Helm MD, Solomon SA, Caras-Quintero D, Ingleson MJ (2011) Simple Inexpensive Boron Electrophiles for Direct Arene Borylation. Chem Commun 47:12459–12461.
https://doi.org/10.1039/c1cc14226g
37. Del Grosso A, Carrillo JA, Ingleson MJ (2015) Regioselective Electrophilic Borylation of
Haloarenes. Chem Commun 51:2878–2881. https://doi.org/10.1039/c4cc10153g
38. Prokofjevs A, Kampf JW, Vedejs E (2011) A Boronium Ion with Exceptional Electrophilicity.
Angew Chem Int Ed 50:2098–2101. https://doi.org/10.1002/anie.201005663
Y. Soltani and F.-G. Fontaine
18. García-Cuadrado D, Braga AAC, Maseras F, Echavarren AM (2006) Proton Abstraction Mechanism for the Palladium-Catalyzed Intramolecular Arylation. J Am Chem Soc 128:1066–1067.
https://doi.org/10.1021/ja056165v
19. Lafrance M, Fagnou K (2006) Palladium-Catalyzed Benzene Arylation: Incorporation of
Catalytic Pivalic Acid as a Proton Shuttle and a Key Element in Catalyst Design. J Am Chem
Soc 128:16496–16497. https://doi.org/10.1021/ja067144j
20. Lafrance M, Rowley CN, Woo TK, Fagnou K (2006) Catalytic Intermolecular Direct Arylation
of Perfluorobenzenes. J Am Chem Soc 128:8754–8756. https://doi.org/10.1021/ja062509l
21. U. S. Food and Drug Administration/Center for Biologics Evaluation and Research, CDER
(2015) Guidance for Industry Q3D Elemental Impurities. Food Drug Adm 1–85
22. Usluer Ö, Abbas M, Wantz G, Vignau L, Hirsch L, Grana E, Brochon C, Cloutet E, Hadziioannou G (2014) Metal Residues in Semiconducting Polymers: Impact on the Performance
of Organic Electronic Devices. ACS Macro Lett 3:1134–1138. https://doi.org/10.1021/mz5
00590d
23. Welch GC, Juan RRS, Masuda JD, Stephan DW (2006) Reversible, Metal-Free Hydrogen
Activation. Science 314:1124–1126. https://doi.org/10.1126/science.1134230
24. Fontaine FG, Stephan DW (2017) On the Concept of Frustrated Lewis Pairs. Philos Trans R
Soc A Math Phys Eng Sci 375:1–8. https://doi.org/10.1098/rsta.2017.0004
25. Muetterties EL (1959) Synthesis of Aryldichloroboranes. J Am Chem Soc 81:2597–2597.
https://doi.org/10.1021/ja01519a079
26. Muetterties EL, Tebbe FN (1968) Dichloroboronation of Aromatic Hydrocarbons. Mechanistic
Aspects. Inorg Chem 7:2663–2664. https://doi.org/10.1021/ic50070a048
27. Muetterties EL (1967) The Chemistry of Boron and its Compounds. Wiley, New York
28. Muetterties EL (1960) Synthesis of Organoboranes. J Am Chem Soc 82:4163–4166. https://
doi.org/10.1021/ja01501a010
29. Bagutski V, Del Grosso A, Carrillo JA, Cade IA, Helm MD, Lawson JR, Singleton PJ, Solomon
SA, Marcelli T, Ingleson MJ (2013) Mechanistic Studies into Amine-Mediated Electrophilic
Arene Borylation and its Application in MIDA Boronate Synthesis. J Am Chem Soc 135:474–
487. https://doi.org/10.1021/ja3100963
30. Davis FA, Dewar MJS (1960) New Heteroaromatic Compounds. A Derivative of 10,9Borathiarophenanthrene. J Org Chem 25:3511–3515. https://doi.org/10.1021/ja01015a039
31. Genaev AM, Nagy SM, Salnikov GE, Shubin VG (2000) Intramolecular Borylation Reaction
Catalyzed by Lewis Acid: Preparation of 1H-2,1-Benzazaborole Derivatives. Chem Commun
1587–1588. https://doi.org/10.1039/B003999N
32. Ishida N, Moriya T, Goya T, Murakami M (2010) Synthesis of Pyridine-Borane Complexes
via Electrophilic Aromatic Borylation. J Org Chem 75:8709–8712. https://doi.org/10.1021/
jo101920p
33. Del Grosso A, Pritchard RG, Muryn CA., Ingleson MJ, (2010) Chelate Restrained Boron
Cations for Intermolecular Electrophilic Arene Borylation. Organometallics 29:241–249.
https://doi.org/10.1021/om900893g
34. Del Grosso A, Singleton PJ, Muryn CA, Ingleson MJ (2011) Pinacol Boronates by Direct
Arene Borylation with Borenium Cations. Angew Chem Int Ed 50:2102–2106. https://doi.
org/10.1002/anie.201006196
35. Solomon SA, Del Grosso A, Clark ER, Bagutski V, McDouall JJW, Ingleson MJ (2012) Reactivity of Lewis Acid Activated Diaza- and Dithiaboroles in Electrophilic Arene Borylation.
Organometallics 31:1908–1916. https://doi.org/10.1021/om201228e
36. Del Grosso A, Helm MD, Solomon SA, Caras-Quintero D, Ingleson MJ (2011) Simple Inexpensive Boron Electrophiles for Direct Arene Borylation. Chem Commun 47:12459–12461.
https://doi.org/10.1039/c1cc14226g
37. Del Grosso A, Carrillo JA, Ingleson MJ (2015) Regioselective Electrophilic Borylation of
Haloarenes. Chem Commun 51:2878–2881. https://doi.org/10.1039/c4cc10153g
38. Prokofjevs A, Kampf JW, Vedejs E (2011) A Boronium Ion with Exceptional Electrophilicity.
Angew Chem Int Ed 50:2098–2101. https://doi.org/10.1002/anie.201005663