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P. M. Kathe et al.
Cluster
Synlett
scope, point to the robustness of the protocol, which is suit-
able for both aryl and alkyl ethers. Moreover, a deprotec-
tion of an N-allylamide has been achieved.
(7) (a) Huang, G.; Ke, M.; Tao, Y.; Chen, F. J. Org. Chem. 2020, 85,
5321; corrigendum: J. Org. Chem.; 2020, 85, 6830. (b) Gao, W.;
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Funding Information
Financial support from the German Academic Exchange Service New
Delhi, the Deutscher Akademischer Austauschdienst (fellowship for
P.K.), and the University of Tübingen is gratefully acknowledged.GermanAcademic
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(8) Ghosh, B.; Kulkarni, S. S. Chem. Asian J. 2020, 15, 450.
(9) Ikeuchi, K.; Murasawa, K.; Ohara, K.; Yamada, H. Org. Lett. 2019,
21, 6638.
(10) Kathe, P. M.; Caciuleanu, A.; Berkefeld, A.; Fleischer, I. J. Org.
Chem. 2020, 85, 15183.
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Supporting Information
Supporting information for this article is available online at
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(16) 2-Methoxyphenol (2a): Typical Procedure
In a glove box, a flame-dried 15 mL Schlenk tube was charged
with [Ni(PMe3)4H]N(SO2CF3)2 (1.6 mg, 2.48 mol, 1 mol%). The
Schlenk tube was removed from the glove box and anhyd THF
(1.5 mL, 0.16 M) was added. 1-(Allyloxy)-2-methoxybenzene
(1a; 41.1 mg, 0.250 mmol, 1 equiv) was then added under an
argon counterflow and the mixture was stirred at RT for 30 min.
TsOH·H2O (1 equiv) was added, and the mixture was refluxed
for 1 h. The reaction was quenched by addition of EtOAc (2 mL)
and H2O (2 mL), and the mixture was transferred to a separatory
funnel. The aqueous phase was extracted with EtOAc (3 × 5 mL),
and the combined organic phases were dried (MgSO4). Rotary
evaporation gave pure 2a, without any chromatographic purifi-
cation, as a light-brown oil; yield: 26.1 mg (0.21 mmol, 84%).
The NMR spectral data matched those reported in the litera-
ture.17 Note: The glove box setup for the reaction is not neces-
sary: the catalyst can be stored on the bench under an inert
atmosphere.
(17) Song, L. X.; Wang, H. M.; Yang, Y.; Xu, P. Bull. Chem. Soc. Jpn.
2007, 80, 2185.
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1839. (b) Corey, E. J.; Suggs, J. W. J. Org. Chem. 1973, 38, 3224.
(c) Varela-Álvarez, A.; Sordo, J. A.; Piedra, E.; Nebra, N.;
Cadierno, V.; Gimeno, J. Chem. Eur. J. 2011, 17, 10583.
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