10.1002/cssc.201900928
ChemSusChem
COMMUNICATION
[8]
a) V. P. Naydyonov, V. G. Syromyatnikov, Funct. Mater. 2002, 9,
508-512; b) H. Niu, H. Kang, J. Cai, C. Wang, X. Bai, W. Wang,
Polym. Chem. 2011, 2, 2804-2817; c) V. Sannasi, D. Jeyakumar,
ChemistrySelect 2018, 3, 1004-1014; For a review see: d) T.
Manifar, S. Rohani, Can. J. Chem. Eng. 2004, 82, 323-334.
O. Drzyzga, Chemosphere 2003, 53, 809-818.
organic layer was extracted with EtOAc (2 × 20 mL) and the
combined organic phases were washed with brine and dried over
sodium sulfate. The solvent was removed in vacuo and the
residue was purified by column chromatography using a hexane:
ethyl acetate system (5:1). [a] Activated at 130 °C under vacuum
for 2 h.
[9]
[10]
R. W. Layer, in Kirk‐Othmer Encyclopedia of Chemical Technology,
2000.
[11]
[12]
H. Batmani, N. Noroozi Pesyan, F. Havasi, Appl. Organomet. Chem.
2018, 32, n/a.
a) Q. Yang, X. Lei, Z. Yin, Z. Deng, Y. Peng, Synthesis 2019, 51,
538-544; b) Y. Han, M. Zhang, Y.-Q. Zhang, Z.-H. Zhang, Green
Chem. 2018, 20, 4891-4900; c) V. Hardouin Duparc, G. L. Bano, F.
Schaper, ACS Catal. 2018, 8, 7308-7325; d) S. Liu, L. Xu, Asian J.
Org. Chem. 2018, 7, 1856-1863.
Acknowledgments
We acknowledge the Canada Research Chair Foundation (to
C.J.Li), the CFI, FQRNT Center for Green Chemistry and
Catalysis, NSERC and McGill University for financial support. The
authors thank Z. Qiu for experimental advice and A. A. H.
Elmehriki for proofreading. A.D.-H. thanks CONACYT for financial
support.
[13]
a) Z. Yi, M. Huang, Y. Wan, X. Zhu, Synthesis 2018, 50, 3911-3920;
b) Q. A. Lo, D. Sale, D. C. Braddock, R. P. Davies, ACS Catal. 2018,
8, 101-109; c) R. B. Sonawane, N. K. Rasal, D. S. Bhange, S. V.
Jagtap, ChemCatChem 2018, 10, 3907-3913.
a) S. M. Crawford, C. A. Wheaton, V. Mishra, M. Stradiotto, Can. J.
Chem. 2018, 96, 578-586; b) A. Mukherjee, D. A. Hrovat, M. G.
Richmond, S. Bhattacharya, Dalton Trans. 2018, 47, 10264-10272.
T. V. Nykaza, J. C. Cooper, G. Li, N. Mahieu, A. Ramirez, M. R.
Luzung, A. T. Radosevich, J. Am. Chem. Soc. 2018, 140, 15200-
15205.
[14]
[15]
Keywords: phenol • hydrogen borrowing • amine diarylation •
palladium catalysis • heterogeneous catalysis
[16]
[17]
[18]
M. Xiong, Z. Gao, X. Liang, P. Cai, H. Zhu, Y. Pan, Chem. Commun.
2018, 54, 9679-9682.
Z.-Y. Tian, X.-X. Ming, H.-B. Teng, Y.-T. Hu, C.-P. Zhang, Chem. -
Eur. J. 2018, 24, 13744-13748.
[1]
a) K. Katoh, M. Kumasaki, Y. Wada, M. Arai, Sci. Technol. Energ.
Mater. 2007, 68, 9-13; b) A. B. Shehata, M. A. Hassan, M. A. Nour,
J. Hazard. Mater. 2003, 102, 121-136.
a) F. M. Moghaddam, R. Pourkaveh, M. Gholamtajari, Appl.
Organomet. Chem. 2018, 32; b) G. Singh, M. Kumar, V. Bhalla,
Green Chem. 2018, 20, 5346-5357.
a) Y. Shimomoto, R. Matsubara, M. Hayashi, Adv. Synth. Catal.
2018, 360, 3297-3305; b) For a review see: S. A. Girard, H. Huang,
F. Zhou, G.-J. Deng, C.-J. Li, Org. Chem. Front. 2015, 2, 279-287.
a) D. Maiti, Chem. Commun. 2011, 47, 8340-8342.b) K. Nejati, S.
Ahmadi, M. Nikpassand, P. D. Kheirollahi Nezhad, E. Vessally, RSC
Adv. 2018, 8, 19125-19143.c) W. Xu, Z. Huang, X. Ji, J.-P. Lumb,
ACS Catal. 2019, Ahead of Print.
H. Zeng, Z. Qiu, A. Domínguez-Huerta, Z. Hearne, Z. Chen, C.-J.
Li, ACS Catal. 2017, 7, 510-519.
a) Z. Chen, H. Zeng, S. A. Girard, F. Wang, N. Chen, C.-J. Li,
Angew. Chem. 2015, 54, 14487-14491; b) Z. Qiu, J.-S. Li, C.-J. Li,
Chem. Sci. 2017, 8, 6954-6958; c) A. Dominguez Huerta, I.
Perepichka, C.-J. Li, CommsChem 2018, 1.
[2]
[3]
M. M. Mutlu, G. Erdogdu, J. Anal. Chem. 2011, 66, 660-665.
a) N. E. Gapper, M. L. A. T. M. Hertog, J. Lee, D. A. Buchanan, R.
S. Leisso, Z. Fei, G. Qu, J. J. Giovannoni, J. W. Johnston, R. J.
Schaffer, B. M. Nicolai, J. P. Mattheis, C. B. Watkins, D. R. Rudell,
BMC Plant Biol. 2017, 17, 77/71-77/18; b) J. Lee, J. P. Mattheis, D.
R. Rudell, Postharvest Biol. Technol. 2012, 68, 32-42; c) R. Leisso,
D. Buchanan, J. Lee, J. Mattheis, D. Rudell, J. Agric. Food Chem.
2013, 61, 1373-1387.
[19]
[20]
[4]
[5]
L. Wang, D. Zhang, H. Wu, Y. Xie, G. Dong, Proc. Inst. Mech.
Eng., Part J. 2017, 231, 1527-1536.
M.-R. Chao, W.-M. Li, L.-L. Zhu, H.-H. Ma, X.-B. Wang, Chem. Pap.
[21]
[22]
2015, 69, 1004-1011.
[6]
a) J. Cui, S. Zhang, Color. Technol. 2018, 134, 381-389; b) A. R.
Salimi Beni, M. Karami, B. Hosseinzadeh, R. Ghahary, J. Mater.
Sci.: Mater. Electron. 2018, 29, 6323-6336; c) X. Wang, Z. Zhong,
S. Zhao, T. Guo, J.-X. Jiang, J. Zou, L. Ying, J. Peng, Y. Cao, Org.
Electron. 2018, 55, 157-164.
[23]
[24]
J.-S. Li, Z. Qiu, C.-J. Li, Adv. Synth. Catal. 2017, 359, 3648-3653.
Z. Dobrovolná, L. Červený, Res. Chem. Intermed. 2000, 26, 489-
497.
[7]
L. Janovec, J. Janockova, M. Matejova, E. Konkolova, H. Paulikova,
D. Lichancova, L. Junosova, S. Hamulakova, J. Imrich, M.
Kozurkova, Bioorg. Chem. 2019, 83, 487-499.
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