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COMMUNICATION
Journal Name
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In conclusion, we have developed an efficient method for the
Murphy, J. Lawrence, K. Kawamura, C. Incarvito and J.
DOI: 10.1039/D0CC02889D
synthesis of o-borylphenols through the Ru-catalyzed regio- and
Hartwig, J. Am. Chem. Soc., 2006, 128, 13684–13685. b) A.
Cook, S. Schimler, A. Matzger and M. Sanford, Science,
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site-selective sp C–H borylation of aryl phosphinites utilizing
phosphorus as a removable directing group. The reaction was
also applicable to aryl phosphites, enabling a highly useful one-
pot borylation reaction using phenol as a starting material.
These results open up new utilization of ruthenium catalysis in
the directed C–H borylation chemistry.
2
016, 351, 1421–1424. c) W. Yao, J. Yang and F.
Hao, Chemsuschem, 2019, 13, 121–125. d) ref 11e.
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4 K. Fukuda, N. Iwasawa and J. Takaya, Angew. Chem. Int. Ed.,
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019, 58, 2850–2853.
5 a) R. Bedford and M. Limmert, J. Org. Chem., 2003, 68, 8669–
682. b) S. Oi, S. Watanabe, S. Fukita and Y.
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This research was supported by JSPS KAKENHI Grant Numbers
Inoue, Tetrahedron Lett., 2003, 44, 8665–8668. c) R. Bedford,
S. Coles, M. Hursthouse and M. Limmert, Angew. Chem. Int.
Ed., 2003, 42, 112–114. d) M. Carrión and D. Cole-
Hamilton, Chem. Commun., 2006, 4527–4529. e) R. Bedford,
M. Betham, A. Caffyn, J. Charmant, L. Lewis-Alleyne, P. Long,
D. Polo-Cerón and S. Prashar, Chem. Commun., 2008, 990–
92. f) Q.-S. Liu, D.-Y. Wang, J.-F. Yang, Z.-Y. Ma and M.
Ye, Tetrahedron, 2017, 73, 3591–3595.
6 A double borylation product was not formed possibly due to
steric repulsion in the second C–H activation step. The
excellent selectivity for the mono-borylation was also
observed in the borylation of arylphosphines (ref 14).
17 The reaction of 2-pyridyl diphenylphosphinite did not proceed.
4 2
8 Strong reductant and oxidant such as LiAlH and I are used
for the removal of carbamate and thiomethyl ether groups in
ref 6 and 7.
9 A similar mechanism involving a reversible C–H activation step
was also proposed in the previously reported C–H borylation
reaction of tertiary phosphines. See ref 14.
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7H03019 (Gran-in-Aid for Scientific Research (B)), 18H04646
(
Hybrid Catalysis), and JST, PRESTO Grant Number JY290145,
Japan.
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Conflicts of interest
There are no conflicts to declare.
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Notes and references
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Ortho-selective borylation of anisole derivatives was reported.
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Catal., 2018, 8, 5017–5022.
0 In the cases of coordinative directing groups, regioisomers
borylated at meta- and para-positions were often obtained
depending on a substituent on the arene. See ref 6 and 7.
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2 An electrophilic borylation reaction of indoles and pyrroles
with borenium ions catalyzed by ruthenium complexes was
reported, see; T. Stahl, K. Müther, Y. Ohki, K. Tatsumi and M.
Oestreich, J. Am. Chem. Soc., 2013, 135, 10978–10981.
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