C
T. Yasukawa et al.
Cluster
Synlett
Table 2 Recovery and Reuse of Catalysts
Zhou, J.; Li, X.; Ma, J. New J. Chem. 2014, 38, 4622. (d) Jiao, N.; Li,
Z.; Wang, Y.; Liu, J.; Xia, C. RSC Adv. 2015, 5, 26913. (e) Long, Y.;
Liang, K.; Niu, J.; Tong, X.; Yuan, B.; Ma, J. New J. Chem. 2015, 39,
2988. (f) Gautam, P.; Dhiman, M.; Polshettiwar, V.; Bhanage, B.
M. Green Chem. 2016, 18, 5890. (g) Sun, X.; Zheng, Y.; Sun, L.;
Lin, Q.; Su, H.; Qi, C. Nano-Struct. Nano-Objects 2016, 5, 7.
(h) Zawartka, W.; Pośpiech, P.; Cypryk, M.; Trzeciak, A. M. J. Mol.
Catal. A: Chem. 2016, 417, 76.
O
PPD-100 (2 mol%)
K2CO3 (1.5 equiv)
I
+
PhB(OH)2
Ph
anisole (0.2 M), 100 °C, 5 h
CO balloon
1a
(1.5 equiv)
3aa
2a
Reactivation with H2
Wash with H2O,
MeOH, acetone
(8) (a) Cai, M.; Zheng, G.; Zha, L.; Peng, J. Eur. J. Org. Chem. 2009,
1585. (b) Wan, Y.; Song, F.; Ye, T.; Li, G.; Liu, D.; Lei, Y. Appl.
Organomet. Chem. 2019, 33, e4714.
(9) (a) Niu, J.-R.; Huo, X.; Zhang, F.-W.; Wang, H.-B.; Zhao, P.; Hu,
W.-Q.; Ma, J.; Li, R. ChemCatChem 2013, 5, 349. (b) Niu, J.; Liu,
M.; Wang, P.; Long, Y.; Xie, M.; Li, R.; Ma, J. New J. Chem. 2014,
38, 1471.
Dry in vacuo
Filtration
100 °C, overnight
under H2
Crude
mixture
Catalysts
and K2CO3
Recovered
catalysts
Run
Scale (mmol)
3aa (%)a
1
2
3
4
5
0.80
0.79
0.77
0.76
0.74
96
94
93
92
88
(10) Bhanage, B.; Qureshi, Z.; Deshmukh, K.; Tambade, P. Synthesis
2011, 243.
(11) Khedkar, M. V.; Tambade, P. J.; Qureshi, Z. S.; Bhanage, B. M. Eur.
J. Org. Chem. 2010, 6981.
(12) Wang, Z.-J.; Wang, X.-Y.; Wang, X.; Liang, Z.-W.; Xu, X. Catal.
Commun. 2017, 101, 10.
(13) (a) Favier, I.; Pla, D.; Gómez, M. Chem. Rev. 2020, 120, 1146.
(b) Cong, H.; Porco, J. A. ACS Catal. 2012, 2, 65. (c) Pla, D.; Gómez,
M. ACS Catal. 2016, 6, 3537.
a Determined by GC analysis with 1,3,5-trimethoxybenzene as internal
standard.
(14) (a) Kobayashi, S.; Okumura, M.; Akatsuka, Y.; Miyamura, H.;
Ueno, M.; Oyamada, H. ChemCatChem 2015, 7, 4025.
(b) Miyamura, H.; Suzuki, A.; Yasukawa, T.; Kobayashi, S. J. Am.
Chem. Soc. 2018, 140, 11325.
Funding Information
(15) Miyamura, H.; Yasukawa, T.; Zhu, Z.; Kobayashi, S. Adv. Synth.
Catal. 2020, 362, 353.
(16) Ishiyama, T.; Kizaki, H.; Hayashi, T.; Suzuki, A.; Miyaura, N.
J. Org. Chem. 1998, 63, 4726.
This work was supported in part by a Grant-in-Aid for Scientific Re-
search from JSPS, the University of Tokyo, and MEXT (Japan), JST.
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(17) Carbonylative Suzuki–Miyaura Coupling Reaction; Typical
Procedure (Table 1, Entry 6): Phenylboronic acid (73.2 mg, 0.6
mmol, 1.5 equiv), K2CO3 (82.9 mg, 0.6 mmol, 1.5 equiv), and
PPD-100 (40.0 mg with 0.1 mmol/g loading of Pd, 0.004 mmol,
1 mol%) were combined in a two-neck glass tube equipped with
a magnetic stirring bar. p-Iodotoluene (87.2 mg, 0.4 mmol, 1.0
equiv) was dissolved in anisole (2.0 mL, 0.2 M) and the resulting
solution was added to the glass tube using a syringe. A balloon
of carbon monoxide, equipped with rubber band and a two-way
stopcock, was connected to the glass tube through a needle, and
the bubbling of CO was started by opening the two-way stop-
cock. After starting to input CO, the mixture was stirred for 5
hours at 100 °C. After cooling to room temperature, the reaction
mixture was diluted and washed with diethyl ether and the
solid catalysts were filtrated off with a membrane filter. The
mixture was concentrated, and purified with preparative TLC to
afford the desired product, phenyl(p-tolyl)methanone, in 93%
yield.
Supporting Information
Supporting information for this article is available online at
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References and Notes
(1) Surana, K.; Chaudhary, B.; Diwaker, M.; Sharma, S. MedChem-
Comm 2018, 9, 1803.
(2) Wu, S.-B.; Long, C.; Kennelly, E. J. Nat. Prod. Rep. 2014, 31, 1158.
(3) Boscá, F.; Miranda, M. A. J. Photochem. Photobiol. B 1998, 43, 1.
(4) Gore, P. H. Chem. Rev. 1955, 55, 229.
(5) Ishiyama, T.; Kizaki, H.; Miyaura, N.; Suzuki, A. Tetrahedron Lett.
1993, 34, 7595.
(6) (a) Wu, X.-F.; Neumann, H.; Beller, M. Chem. Soc. Rev. 2011, 40,
4986. (b) Zhu, Z.; Zhang, W.; Gao, Z. Prog. Chem. 2016, 28, 1626.
(7) (a) Cai, M.; Peng, J.; Hao, W.; Ding, G. Green Chem. 2011, 13, 190.
(b) Niu, J.; Xie, M.; Zhu, X.; Long, Y.; Wang, P.; Li, R.; Ma, J. J. Mol.
Catal. A: Chem. 2014, 392, 247. (c) Zhu, X.; Niu, J.; Zhang, F.;
© 2020. Thieme. All rights reserved. Synlett 2020, 31, A–C