10.1002/ejic.201900692
European Journal of Inorganic Chemistry
FULL PAPER
3206-3209; (c) W.-C. Chen, Y.-C. Hsu, C.-Y. Lee, G. P. A. Yap,
T.-G. Ong, Organometallics 2013, 32, 2435-2442.
(a) W.-C. Chen, C.-Y. Lee, B.-C. Lin, Y.-C. Hsu, J.-S. Shen, C.-P.
Hsu, G. P. A. Yap, T.-G. Ong, J. Am. Chem. Soc. 2014, 136, 914-
917; (b) W.-C. Chen, J.-S. Shen, T. Jurca, C.-J. Peng, Y.-H. Lin,
Y.-P. Wang, W.-C. Shih, G. P. A. Yap, T.-G. Ong, Angew. Chem.,
Int. Ed. 2015, 54, 15207-15212; (c) W.-C. Chen, W.-C. Shih, T.
Jurca, L. Zhao, D. M. Andrada, C.-J. Peng, C.-C. Chang, S.-k. Liu,
Y.-P. Wang, Y.-S. Wen, G. P. A. Yap, C.-P. Hsu, G. Frenking, T.-
G. Ong, J. Am. Chem. Soc. 2017, 139, 12830-12836.
Y.-C. Hsu, V. C.-C. Wang, K.-C. Au-Yeung, C.-Y. Tsai, C.-C.
Chang, B.-C. Lin, Y.-T. Chan, C.-P. Hsu, G. P. A. Yap, T. Jurca, T.-
G. Ong, Angew. Chem., Int. Ed. 2018, 57, 4622-4626.
A.-H. Liu, Y.-L. Dang, H. Zhou, J.-J. Zhang, X.-B. Lu,
ChemCatChem 2018, 10, 2686-2692.
J. E. Walley, G. Breiner, G. Wang, D. A. Dickie, A. Molino, J. L.
Dutton, D. J. D. Wilson, J. R. J. Gilliard, Chem. Commun. 2019,
55, 1967-1970.
(a) W.-C. Shih, Y.-T. Chiang, Q. Wang, M.-C. Wu, G. P. A. Yap, L.
Zhao, T.-G. Ong, Organometallics 2017, 36, 4287-4297; (b)
Y.-C. Hsu, J.-S. Shen, B.-C. Lin, W.-C. Chen, Y.-T. Chan, W.-M.
Ching, G. P. A. Yap, C.-P. Hsu, T.-G. Ong, Angew. Chem., Int. Ed.
2015, 54, 2420-2424.
(a) C. C. Roberts, D. M. Matías, M. J. Goldfogel, S. J. Meek, J.
Am. Chem. Soc. 2015, 137, 6488-6491; (b) M. J. Goldfogel, C.
C. Roberts, S. J. Meek, J. Am. Chem. Soc. 2014, 136, 6227-
6230.
C. Pranckevicius, L. Fan, D. W. Stephan, J. Am. Chem. Soc.
2015, 137, 5582-5589.
A. L. Liberman-Martin, R. H. Grubbs, Organometallics 2017,
36, 4091-4094.
(a) K. Tamao, K. Sumitani, M. Kumada, J. Am. Chem. Soc.
1972, 94, 4374-4376; (b) R. J. P. Corriu, J. P. Masse, J. Chem.
Soc., Chem. Commun. 1972, 144a-144a.
Notes
The authors declare no competing financial interest.
[3]
[4]
Keywords: nickel • carbodicarbene • C‒O Cleavage •
Grignard reagent • anisole
Experimental section
General Information
All air-sensitive manipulations were performed under an
1
atmosphere of N2 using Schlenk technique or in a glovebox. H
and 13C NMR Spectra were recorded on Bruker Avance 400 or
500 MHz spectrometer using the residual proton of the
[5]
[6]
1
deuterated solvent as a reference (CDCl3, H NMR: 7.24 ppm.
13C NMR: 77.0 ppm). Chemical shifts are reported in ppm (δ);
coupling constants J, are reported in Hz. Standard abbreviations
are used: s = singlet, d = doublet, dd = doublet of doublets, t =
triplet, q = quartet, and m = multiplet. Column chromatography
was performed by using silica gel (spherical, 40-63 mesh).
Analytical TLC was performed on Merck silica gel plates with
QF-254 indicator. GC analyses were performed on an Agilent
Technologies 7890 GC instrument. High resolution mass
Spectrum were obtained with a JEOL, JMS-700 (EI, ESI or
APCI) spectrometer with a resolution of 8000(3000) (5% valley
definition). Single crystals of 3aa, 3ka, and 5na were collected
from concentrated CH2Cl2 solution layered with hexane. A
suitable crystal was selected for data collection under N2 stream
at 100 K on a 'Bruker APEX-II CCD' diffractometer. The crystal
was kept at 100 K during data collection. Using Olex2, the
structure was solved with the SHELXT structure solution
program using Intrinsic Phasing and refined using the SHELXT
refinement package of Least Squares minimization. All reagents
were purchased from Acros, Alfa Aesar, Sigma-Aldrich, and TCI
and used without further purification. Reagent grade solvents
were used for chromatography.
[7]
[8]
[9]
[10]
[11]
[12]
[13]
E. Wenkert, E. L. Michelotti, C. S. Swindell, J. Am. Chem. Soc.
1979, 101, 2246-2247.
(a) D.-G. Yu, B.-J. Li, Z.-J. Shi, Acc. Chem. Res. 2010, 43, 1486-
1495; (b) B. M. Rosen, K. W. Quasdorf, D. A. Wilson, N. Zhang,
A.-M. Resmerita, N. K. Garg, V. Percec, Chem. Rev. 2011, 111,
1346-1416; (c) J. Cornella, C. Zarate, R. Martin, Chem. Soc.
Rev. 2014, 43, 8081-8097; (d) M. Tobisu, N. Chatani, Acc.
Chem. Res. 2015, 48, 1717-1726; (e) H. Zeng, Z. Qiu, A.
Domínguez-Huerta, Z. Hearne, Z. Chen, C.-J. Li, ACS Catal.
2017, 7, 510-519.
J. W. Dankwardt, Angew. Chem., Int. Ed. 2004, 43, 2428-2432.
(a) B.-T. Guan, S.-K. Xiang, B.-Q. Wang, Z.-P. Sun, Y. Wang, K.-
Q. Zhao, Z.-J. Shi, J. Am. Chem. Soc. 2008, 130, 3268-3269; (b)
B.-T. Guan, S.-K. Xiang, T. Wu, Z.-P. Sun, B.-Q. Wang, K.-Q.
Zhao, Z.-J. Shi, Chem. Commun. 2008, 1437-1439.
D.-G. Yu, B.-J. Li, S.-F. Zheng, B.-T. Guan, B.-Q. Wang, Z.-J. Shi,
Angew. Chem., Int. Ed. 2010, 49, 4566-4570.
Representative procedure for nickel-catalyzed Kumada
cross-coupling
In a N2-filled glove-box, a 4 mL oven-dried tube equipped with a
stir bar was charged with Ni(cod)2 (0.05 mmol, 14 mg), and C1-
CDC (0.05 mmol, 18 mg) in 0.7 mL m-xylene and stirred for 10
min
at
ambient
temperature.
Sequentially,
2-
[14]
[15]
methoxynaphthalene (0.50 mmol, 79 mg), and p-tolylMgBr (1.0
M in THF, 0.75 mmol, 0.75 mL) were added. Reaction mixture
was sealed and removed from the glove-box and maintained at
60 °C for 4 h in an oil-bath. After cooling the reaction mixture to
room temperature, it was quenched by 2-3 drops of water, and
purified by flash chromatography using hexanes. The product
was isolated in 95% yield. Any deviations from this protocol are
specified in the table’s footnote.
[16]
[17]
[18]
L.-G. Xie, Z.-X. Wang, Chem. Eur. J. 2011, 17, 4972-4975.
P. Leowanawat, N. Zhang, V. Percec, J. Org. Chem. 2012, 77,
1018-1025.
[19]
[20]
G. J. Harkness, M. L. Clarke, Catal. Sci. Technol. 2018, 8, 328-
334.
[1]
(a) S. Díez-González, N. Marion, S. P. Nolan, Chem. Rev. 2009,
109, 3612-3676; (b) B. Maji, Asian J. Org. Chem. 2018, 7, 70-
84; (c) V. P. Reddy, A. Vadapalli, E. Sinn, N. Hosmane, J.
Organomet. Chem. 2013, 747, 43-50; (d) T. N. Tekavec, J.
Louie, in N-Heterocyclic Carbenes in Transition Metal
Catalysis (Ed.: F. Glorius), Springer Berlin Heidelberg, Berlin,
Heidelberg, 2007, pp. 159-192; (e) P.-C. Chiang, J. W. Bode,
in N-Heterocyclic Carbenes: From Laboratory Curiosities to
Efficient Synthetic Tools, The Royal Society of Chemistry,
2011, pp. 399-435; (f) A. P. Prakasham, P. Ghosh, Inorg.
Chim. Acta 2015, 431, 61-100.
(a) M. Tobisu, T. Takahira, T. Morioka, N. Chatani, J. Am.
Chem. Soc. 2016, 138, 6711-6714; (b) M. Tobisu, T. Takahira,
A. Ohtsuki, N. Chatani, Org. Lett. 2015, 17, 680-683.
T. Hostier, Z. Neouchy, V. Ferey, D. Gomez Pardo, J. Cossy,
Org. Lett. 2018, 20, 1815-1818.
(a) E. M. Wiensch, D. P. Todd, J. Montgomery, ACS Catal.
2017, 7, 5568-5571; (b) M. Tobisu, A. Yasutome, H. Kinuta,
K. Nakamura, N. Chatani, Org. Lett. 2014, 16, 5572-5575; (c)
M. J. Iglesias, A. Prieto, M. C. Nicasio, Org. Lett. 2012, 14,
4318-4321.
[21]
[22]
[2]
(a) S.-k. Liu, W.-C. Shih, W.-C. Chen, T.-G. Ong, ChemCatChem
2018, 10, 1483-1498; (b) C. A. Dyker, V. Lavallo, B.
Donnadieu, G. Bertrand, Angew. Chem., Int. Ed. 2008, 47,
[23]
[24]
Z.-C. Cao, Q.-Y. Luo, Z.-J. Shi, Org. Lett. 2016, 18, 5978-5981.
M. Tobisu, A. Yasutome, K. Yamakawa, T. Shimasaki, N.
Chatani, Tetrahedron 2012, 68, 5157-5161.
This article is protected by copyright. All rights reserved.