4 FLP-Mediated C–H-Activation
161
References
1. Frankowski KJ, Liu R, Milligan GL, Moeller KD, Aubé J (2015) Practical Electrochemical
Anodic Oxidation of Polycyclic Lactams for Late Stage Functionalization. Angew Chem Int
Ed 54:10555–10558. https://doi.org/10.1002/anie.201504775
2. Abrams DJ, Provencher PA, Sorensen EJ (2018) Recent Applications of C-H Functionalization
in Complex Natural Product Synthesis. Chem Soc Rev 47:8925–8967. https://doi.org/10.1039/
c8cs00716k
3. Davies DL, Donald SMA, Macgregor SA (2005) Computational Study of the Mechanism of
Cyclometalation by Palladium Acetate. J Am Chem Soc 127:13754–13755. https://doi.org/
10.1021/ja052047w
4. Wheland GW (1942) A Quantum Mechanical Investigation of the Orientation of Substituents
in Aromatic Molecules. J Am Chem Soc 64:900–908. https://doi.org/10.1021/ja01256a047
5. Nguyen P, Blom HP, Westcott SA, Taylor NJ, Marder TB (1993) Synthesis and Structures of
the First Transition-Metal Tris(boryl) Complexes: (η 6 -Arene)Ir(BO 2 C 6 H 4 ) 3 . J Am Chem Soc
115:9329–9330. https://doi.org/10.1021/ja00073a075
6. Cho JY, Tse MK, Holmes D, Maleczka Jr. RE, Smith MR III (2002) Remarkably Selective
Iridium Catalysts for the Elaboration of Aromatic C-H Bonds. Science 295:305–308. https://
doi.org/10.1126/science.1067074
7. Iverson CN, Smith MR (1999) Stoichiometric and Catalytic B-C Bond Formation from Unactivated Hydrocarbons and Boranes. J Am Chem Soc 121:7696–7697. https://doi.org/10.1021/
ja991258w
8. Cho JY, Iverson CN, Smith MR (2000) Steric and Chelate Directing Effects in Aromatic
Borylation. J Am Chem Soc 122:12868–12869. https://doi.org/10.1021/ja0013069
9. Chen H, Schlecht S, Semple TC, Hartwig JF (2000) Thermal, Catalytic, Regiospecific Functionalization of Alkanes. Science 287:1995–1997. https://doi.org/10.1126/science.287.5460.
1995
10. Ishiyama T, Nobuta Y, Hartwig JF, Miyaura N (2003) Room Temperature Borylation of Arenes
and Heteroarenes Using Stoichiometric Amounts of Pinacolborane Catalyzed by Iridium
Complexes in an Inert Solvent. Chem Commun 2924–2925. https://doi.org/10.1039/B311103B
11. Ishiyama T, Takagi J, Ishida K, Miyaura N, Anastasi, NR, Hartwig JF (2002) Mild IridiumCatalyzed Borylation of Arenes. High Turnover Numbers, Room Temperature Reactions, and
Isolation of a Potential Intermediate. J Am Chem Soc 124:390–391. https://doi.org/10.1021/
ja0173019
12. Takagi J, Sato K, Hartwig JF, Ishiyama T, Miyaura N (2002) Iridium-Catalyzed C-H
Coupling Reaction of Heteroaromatic Compounds with Bis(pinacolato)diboron: Regioselective Synthesis of Heteroarylboronates. Tetrahedron Lett 43:5649–5651. https://doi.org/10.
1016/S0040-4039(02)01135-8
13. Ishiyama T, Miyaura N (2006) Iridium-Catalyzed Borylation of Arenes and Heteroarenes via
C-H activation. Pure Appl Chem 78:1369–1375. https://doi.org/10.1351/pac200678071369
14. Larsen MA, Hartwig JF (2014) Iridium-Catalyzed C-H Borylation of Heteroarenes: Scope,
Regioselectivity, Application to Late-Stage Functionalization, and Mechanism. J Am Chem
Soc 136:4287–4299. https://doi.org/10.1021/ja412563e
15. Vanchura BA, Preshlock SM, Roosen PC, Kallepalli VA, Staples RJ, Maleczka Jr. RE,
Singleton DA, Smith MR III (2010) Electronic Effects in Iridium C-H Borylations: Insights
from Unencumbered Substrates and Variation of Boryl Ligand Substituents. Chem Commun
46:7724–7726. https://doi.org/10.1039/c0cc02041a
16. Ryabov AD, Sakodinskaya IK, Yatsimirsky AK (1985) Kinetics and Mechanism of OrthoPalladation of Ring-Substituted N,N-Dimethylbenzylamines. J Chem Soc, Dalton Trans 2629–
2638. https://doi.org/10.1039/DT9850002629
17. García-Cuadrado D, De Mendoza P, Braga AAC, Maseras F, Echavarren AM (2007) ProtonAbstraction Mechanism in the Palladium-Catalyzed Intramolecular Arylation: Substituent
Effects. J Am Chem Soc 129:6880–6886. h https://doi.org/10.1021/ja071034a
161
References
1. Frankowski KJ, Liu R, Milligan GL, Moeller KD, Aubé J (2015) Practical Electrochemical
Anodic Oxidation of Polycyclic Lactams for Late Stage Functionalization. Angew Chem Int
Ed 54:10555–10558. https://doi.org/10.1002/anie.201504775
2. Abrams DJ, Provencher PA, Sorensen EJ (2018) Recent Applications of C-H Functionalization
in Complex Natural Product Synthesis. Chem Soc Rev 47:8925–8967. https://doi.org/10.1039/
c8cs00716k
3. Davies DL, Donald SMA, Macgregor SA (2005) Computational Study of the Mechanism of
Cyclometalation by Palladium Acetate. J Am Chem Soc 127:13754–13755. https://doi.org/
10.1021/ja052047w
4. Wheland GW (1942) A Quantum Mechanical Investigation of the Orientation of Substituents
in Aromatic Molecules. J Am Chem Soc 64:900–908. https://doi.org/10.1021/ja01256a047
5. Nguyen P, Blom HP, Westcott SA, Taylor NJ, Marder TB (1993) Synthesis and Structures of
the First Transition-Metal Tris(boryl) Complexes: (η 6 -Arene)Ir(BO 2 C 6 H 4 ) 3 . J Am Chem Soc
115:9329–9330. https://doi.org/10.1021/ja00073a075
6. Cho JY, Tse MK, Holmes D, Maleczka Jr. RE, Smith MR III (2002) Remarkably Selective
Iridium Catalysts for the Elaboration of Aromatic C-H Bonds. Science 295:305–308. https://
doi.org/10.1126/science.1067074
7. Iverson CN, Smith MR (1999) Stoichiometric and Catalytic B-C Bond Formation from Unactivated Hydrocarbons and Boranes. J Am Chem Soc 121:7696–7697. https://doi.org/10.1021/
ja991258w
8. Cho JY, Iverson CN, Smith MR (2000) Steric and Chelate Directing Effects in Aromatic
Borylation. J Am Chem Soc 122:12868–12869. https://doi.org/10.1021/ja0013069
9. Chen H, Schlecht S, Semple TC, Hartwig JF (2000) Thermal, Catalytic, Regiospecific Functionalization of Alkanes. Science 287:1995–1997. https://doi.org/10.1126/science.287.5460.
1995
10. Ishiyama T, Nobuta Y, Hartwig JF, Miyaura N (2003) Room Temperature Borylation of Arenes
and Heteroarenes Using Stoichiometric Amounts of Pinacolborane Catalyzed by Iridium
Complexes in an Inert Solvent. Chem Commun 2924–2925. https://doi.org/10.1039/B311103B
11. Ishiyama T, Takagi J, Ishida K, Miyaura N, Anastasi, NR, Hartwig JF (2002) Mild IridiumCatalyzed Borylation of Arenes. High Turnover Numbers, Room Temperature Reactions, and
Isolation of a Potential Intermediate. J Am Chem Soc 124:390–391. https://doi.org/10.1021/
ja0173019
12. Takagi J, Sato K, Hartwig JF, Ishiyama T, Miyaura N (2002) Iridium-Catalyzed C-H
Coupling Reaction of Heteroaromatic Compounds with Bis(pinacolato)diboron: Regioselective Synthesis of Heteroarylboronates. Tetrahedron Lett 43:5649–5651. https://doi.org/10.
1016/S0040-4039(02)01135-8
13. Ishiyama T, Miyaura N (2006) Iridium-Catalyzed Borylation of Arenes and Heteroarenes via
C-H activation. Pure Appl Chem 78:1369–1375. https://doi.org/10.1351/pac200678071369
14. Larsen MA, Hartwig JF (2014) Iridium-Catalyzed C-H Borylation of Heteroarenes: Scope,
Regioselectivity, Application to Late-Stage Functionalization, and Mechanism. J Am Chem
Soc 136:4287–4299. https://doi.org/10.1021/ja412563e
15. Vanchura BA, Preshlock SM, Roosen PC, Kallepalli VA, Staples RJ, Maleczka Jr. RE,
Singleton DA, Smith MR III (2010) Electronic Effects in Iridium C-H Borylations: Insights
from Unencumbered Substrates and Variation of Boryl Ligand Substituents. Chem Commun
46:7724–7726. https://doi.org/10.1039/c0cc02041a
16. Ryabov AD, Sakodinskaya IK, Yatsimirsky AK (1985) Kinetics and Mechanism of OrthoPalladation of Ring-Substituted N,N-Dimethylbenzylamines. J Chem Soc, Dalton Trans 2629–
2638. https://doi.org/10.1039/DT9850002629
17. García-Cuadrado D, De Mendoza P, Braga AAC, Maseras F, Echavarren AM (2007) ProtonAbstraction Mechanism in the Palladium-Catalyzed Intramolecular Arylation: Substituent
Effects. J Am Chem Soc 129:6880–6886. h https://doi.org/10.1021/ja071034a