Page 7 of 8
Journal of the American Chemical Society
Reactivity Pattern of Frustrated 2-Aminophenylboranes. J. Am. Chem. Soc.
2016, 138, 4860.
b) Esteruelas, M. A.; Olivàn, M.; Vélez, A. POP-Rhodium-Promoted C-H
and B-H Bond Activation and C-B Bond Formation. Organometallics 2015,
34, 1911.
1
2
3
4
5
6
7
8
b) Iashin, V.; Chernichenko, K.; Pápai, I.; Repo, T. Atom-Efficient
Synthesis of Alkynylfluoroborates Using BF3-Based Frustrated Lewis
Pairs. Angew. Chem. Int. Ed. 2016, 55, 14146.
c) Yin, Q.; Klare, H. F. T.; Oestreich, M. Catalytic Friedel – Crafts C-H
Borylation of Electron-Rich Arenes: Dramatic Rate Acceleration by Added
Alkenes. Angew. Chem. Int. Ed. 2017, 56, 3712.
d) Del Grosso, A.; Pritchard, R. G.; Muryn, C. A.; Ingleson, M. J. Chelate
Restrained Boron Cations for Intermolecular Electrophilic Arene
Borylation. Organometallics 2010, 29, 241.
e) Chen, S.; Li, B.; Wang, X.; Huang, Y.; Li, J.; Zhu, H.; Zhao, L.; Frenking,
J.; Roesky, H. W. A C(sp2)-H Dehydrogenation of Heteroarenes and Arenes
by a Functionalized Aluminum Hydride. Chem. Eur. J. 2017, 23, 13633.
f) Liu, Y.; Kehr, G.; Daniliuc, C. G.; Erker, G. Metal-Free Arene and
Heteroarene Borylation Catalyzed by Strongly Electrophilic Bis-boranes.
Chem. Eur. J. 2017, 23, 12141.
c) Press, L. P.; Kosanovich, A. J.; Mcculloch, B. J.; Ozerov, O. V. High-
Turnover Aromatic C-H Borylation Catalyzed by POCOP-Type Pincer
Complexes of Iridium. J. Am. Chem. Soc. 2016, 138, 9487.
d) Ren, H.; Zhou, Y.; Bai, Y.; Cui, C.; Driess, M. Cobalt-Catalyzed
Regioselective Borylation of Arenes : N-Heterocyclic Silylene as an
Electron Donor in the Metal-Mediated Activation of C-H Bonds. Chem.
Eur. J. 2017, 23, 5663.
16 A recent computational study on the B-C bond dissociation enthalpies was
recently published: Wang, J. Y.; Zheng, W. R.; Ding, L. L.; Wang, Y. X.
Computational study on C-B hemolytic bond dissociation enthalpies of
organoboron compounds. New J. Chem. 2017, 41, 1346.
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
37
38
39
40
41
42
43
44
45
46
47
48
49
50
51
52
53
54
55
56
57
58
59
60
17
Marciniec, B.; Jankowska, M.; Pietraszuk, C. New catalytic route to
functionalized vinylboronates. Chem. Commun. 2005, 663.
18
Lee, Y.; Baek, S.; Park, J.; Kim, S.-T.; Tussupbayev, S.; Kim, J.; Baik,
g) Zhang, S.; Han, Y.; He, J.; Zhang, Y. B(C6F5)3-Catalyzed C3-Selective
C-H Borylation of Indoles: Synthesis, Intermediates, and Reaction
Mechanism. J. Org. Chem. 2018, 83, 1377.
M.;
Cho,
S.
H.
Chemoselective
Coupling
of
1,1-
Bis[(pinacolato)boryl]alkanes for the Transition-Metal-Free Borylation of
Aryl and Vinyl Halides: A Combined Experimental and Theoretical
Investigation. J. Am. Chem. Soc. 2017, 139, 976.
11 a) Xu, L.; Wang, G.; Zhang, S.; Wang, H.; Wang, L.; Liu, L.; Jiao, J.; Li,
P. Recent advances in catalytic C-H borylation reactions. Tetrahedron
2017, 73, 7123.
19 Rochette, É.; Boutin, H.; Fontaine, F.-G. Frustrated Lewis Pair Catalyzed
S-H Bond Borylation. Organometallics 2017, 36, 2870.
20
b) Mkhalid, I. A. I.; Barnard, J. H.; Marder, T. B.; Murphy, J. M.; Hartwig,
J. F. C-H Activation for the Construction of C-B Bonds. Chem. Rev. 2009,
110, 890.
a) Lee, C.-I.; Zhou, J.; Ozerov, O. V. Catalytic Dehydrogenative
Borylation of Terminal Alkynes by a SiNN Pincer Complex of Iridium. J.
Am. Chem. Soc. 2013, 135, 3560.
12 a) Cho, J.; Tse, M. K.; Holmes, D.; Maleczka Jr., R. E.; Smith III, M. R.
Remarkably Selective Iridium Catalysts for the Elaboration of Aromatic C-
H Bonds. Science 2002, 295, 305.
b) Romero, E. A.; Jazzar, R.; Bertrand, G. Copper-catalyzed
dehydrogenative borylation of terminal alkynes with pinacolborane. Chem.
Sci. 2017, 8, 165.
21
b) Ishiyama, T.; Takagi, J.; Ishida, K.; Miyaura, N.; Anastasi, N. R.;
Hartwig, J. F. Mild Iridium-Catalyzed Borylation of Arenes. High Turnover
Numbers, Room Temperature Reactions, and Isolation of a Potential
Intermediate. J. Am. Chem. Soc. 2002, 124, 390.
Hasenbeck, M.; Müller, T.; Gellrich, U. Metal-free gem selective
Dimerization of Terminal Alkynes catalyzed by a Pyridonate Borane
Complex. Catal. Sci. Technol. 2019, 9, 2438.
22 a) Wrackmeyer, B. 1,1-organoboration of alkynylsilicon, -germanium, -
tin and –lead compounds. Coord. Chem. Rev. 1995, 145, 125.
b) Kher, G.; Erker, G. Advanced 1,1-carboboration reactions with
pentafluorophenylboranes. Chem. Sci. 2016, 7, 56.
13
Obligacion, J. V; Semproni, S. P.; Chirik, P. J. Cobalt-Catalyzed C-H
Borylation. J. Am. Chem. Soc. 2014, 136, 4133.
14 a) Bagutski, V.; Del Grosso, A.; Carrillo, J. A.; Cade, I. A.; Helm, M. D.;
Lawson, J. R.; Singleton, P. J.; Solomon, S. A.; Marcelli, T.; Ingleson, M.
J. Mechanistic Studies into Amine-Mediated Electrophilic Arene
Borylation and Its Application in MIDA Boronate Synthesis. J. Am. Chem.
Soc. 2013, 135, 474.
23
Zhu, C.; Ma, S. Studies on Palladium-Catalyzed Synthesis of
Dihydrocycloocta[b]indoles and their Thermal Reactivities with Maleimide
or Maleic Anhydride. Adv. Synth. Catal. 2014, 356, 3897.
24
a) Jacobs, E. A.; Chandrasekar, R.; Smith, D. A.; White, C. M.;
b) Prokofjevs, A.; Kampf, J. W.; Vedejs, E. A Boronium Ion with
Exceptional Electrophilicity. Angew. Chem. Int. Ed. 2011, 50, 2098.
c) Del Grosso, A.; Singleton, P. J.; Muryn, C. A.; Ingleson, M. J. Pinacol
Boronates by Direct Arene Borylation with Borenium Cations. Angew.
Chem. Int. Ed. 2011, 50, 2102.
Bochmann, M.; Lancaster, S. J. Facile Hydroboration with Dimethylsulfide
Adducts of Mono- and Bis-(Pentafluorophenyl)Borane. J. Organomet.
Chem. 2013, 730, 44.
b) Dureen, M. A.; Welch, G. C.; Gilbert, T. M.; Stephan, D. W. Heterolytic
Cleavage of Disulfides by Frustrated Lewis Paris. Inorg. Chem. 2009, 48,
9910.
15 a) Hatanaka, T.; Ohki, Y.; Tatsumi, K. C-H Bond Activation/Borylation
of Furans and Thiophenes Catalyzed by a Half-Sandwich Iron N-
Heterocyclic Carbene Complex. Chem. Asian J. 2010, 5, 1657.
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