10.1002/cctc.201700679
ChemCatChem
COMMUNICATION
residue was diluted with H2O solution (10 mL) and extracted with EtOAc
(3×10 mL). The solvent was then evaporated under vacuum. The crude
products were purified by using column chromatography on silica gel
(pentane/ethyl acetate) to give the pure products 2.
350; i) I. Papagiannouli, K. Iliopoulos, D. Gindre, B. Sahraoui, O.
Krupka, V. Smokal, A. Kolendo, S. Couris, Chem. Phys. Lett. 2012, 554,
107.
[5]
a) Y. Qian, D. Bolina, K. Conde-Knapeb, P. Gillespie, S. Hayden, K.
Huang, A. R. Olivier, T. Sato, Q. Xiang, W. Yun, X. Zhang, Bioorg. Med.
Chem. Lett. 2013, 23, 2936; b) S.J. Foster, P. Bruneau, E. R. Walker, R.
M. McMiillan, Br. J. Pharmacol. 1990, 99, 113; c) E. Pontiki, D.
Hadjipavlou-Litina, Med. Res. Rev. 2008, 28, 39; d) C. W. Bird, J. C. W.
Chng, N. H. Rama, A. Saeed, Synth. Commun. 1991, 21, 545; e) M. V.
Peters, R. S. Stoll, R. Goddard, G. Buth, S. Hecht, J. Org. Chem. 2006,
71, 7840; f) W. Wang, J. Chen, Z. Chen, Y. Zeng, X. Zhang, M. Yan, A.
S. C. Chan, Synthesis 2016, 48, 3551; g) S. Murahashi, S. Horiie, J.
Am. Chem. Soc. 1956, 78, 4816.
General procedure for KIE experiment
In a 25 mL sealed tube, a mixture of azobenzene 1a (27.3 mg, 0.15
mmol), azobenzene-d10 1a-d10 (28.8 mg, 0.15 mmol), PdCl2 (5.3 mg, 0.03
mmol, 10 mol%), Mo(CO)6 (63.4 mg, 0.24 mmol, 0.8 eq.), and BQ (0.6
mmol, 2 eq.) in HOAc (2 mL) was stirred at 100 oC under air. After 16 h,
the mixture was cooled to room temperature. The residue was diluted
with H2O solution (10 mL) and extracted with EtOAc (3×10 mL). The
solvent was then evaporated under vacuum. The crude products were
purified by using column chromatography on silica gel (pentane/ethyl
acetate = 6:1) to give the pure products 2a and 2a-d9.
[6]
[7]
a) L. Kollär, Modern Carbonylation Methods; Wiley-VCH, 2008; b) X.-F.
Wu, H. Neumann, ChemCatChem 2012, 4, 447; c) X.-F. Wu, H.
Neumann, M. Beller, ChemSusChem 2013, 6, 229; d ) X.-F. Wu, RSC
Adv. 2016, 6, 83831; e) R. Skoda-Foldes and L. Kollör, Curr. Org.
Chem. 2002, 6, 1097; f) B. Gabriele, R. Mancuso, G. Salerno, Eur. J
Org. Chem. 2012, 6825; g) S. Sumino, A. Fusano, T. Fukuyama, I. Ryu,
Acc. Chem. Res. 2014, 47, 1563.
One-pot synthesis for cyclocarbonylation products (2a)
In a 25 mL sealed tube, aniline (60.5 mg, 0.65 mmol, 1.3 eq.) was added
to a stirred solution of nitrosobenzene (53.5 mg, 0.5 mmol, 1 eq.) in the
solvent of HOAc (5 mL) at 70 oC. After the reaction mixture heated for 18
h, PdCl2 (8.8 mg, 0.05 mmol, 10 mol%), Mo(CO)6 (105.6 mg, 0.4 mmol,
0.8 eq.), and BQ (1 mmol, 2 eq.) were added into the sealed tube. Then
the reaction was stirred at 100 oC under air for 36 h. The residue was
diluted with H2O solution (10 mL) and extracted with EtOAc (3×10 mL).
The solvent was then evaporated under vacuum. The crude products
were purified by using column chromatography on silica gel
(pentane/ethyl acetate = 6:1) to give the pure product 2a in white solid.
a) L. R. Odell, F. Russo, M. Larhed, Synlett 2012, 685; b) T. Morimoto,
K. Kakiuchi, Angew. Chem. Int. Ed., 2004, 43, 5580; c) L. Wu, Q. Liu, R.
Jackstell, M. Beller, Angew. Chem. Int. Ed., 2014, 53, 6310; d) P.
Gautam, B. M. Bhanage, Catal. Sci. Technol., 2015, 5, 4663; e) B. Sam,
B. Breit, M. J. Krische, Angew. Chem. Int. Ed., 2015, 54, 3267; f) S. D.
Friis, A. T. Lindhardt, T. Skrydstrup, Acc. Chem. Res. 2016, 49, 594.
Chemicals Economic Handbook, IHS Markit, 2016.
[8]
[9]
E. M. Simmons, J. F. Hartwig, Angew. Chem. Int. Ed. 2012, 51, 3066.
Acknowledgements
We thank the Chinese Scholarship Council for financial Support.
We thank the analytical department of Leibniz-Institute for
Catalysis at the University of Rostock for their excellent
analytical service here. We appreciate the general support from
Professor Armin Börner and Professor Matthias Beller in LIKAT.
Keywords: carbonylation • azoarenes • synthetic method •
palladium catalyst • cascade process
[1]
a) M. Hedayatullah, J. P. Dechatre, L. Denivelle, Tetrahedron Lett.
1975, 16, 2039; b) M. Hirano, S. Yakabe, H. Chikamori, J. H. Clark, T.
Morimoto, J. Chem. Soc. 1998, 770; c) A. Shaabani, D. G. Lee,
Tetrahedron Lett. 2001, 42, 5833; d) Y. Saiki, H. Sugiura, K. Nakamura,
M. Yamaguchi, T. Hoshi, J. I. Anzai, J. Am. Chem. Soc. 2003, 125,
9268; e) A. K. Flatt, S. M. Dirk, J. C. Henderson, D. E. Shen, J. Su, M.
A. Reed, J. M. Tour, Tetrahedron 2003, 59, 8555; f) H. Naeimi, J. Safari,
A. Heidarnezhad, Dyes Pigm. 2007, 73, 251; g) C. Zhang, N. Jiao,
Angew. Chem. Int. Ed. 2010, 49, 6174.
[2]
a) W. H. Nutting, R. A. Jewell, H. Rapoport, J. Org. Chem. 1970, 35,
505; b) K. Krageloh, G. H. Anderson, P. J. Stang, J. Am. Chem. Soc.
1984, 106, 6015; c) Z. Liu, M. Jiang, J. Mater. Chem. 2007, 17, 4249;
d) F. Hamon, F. Djedaini-Pilard, F. Barbot, C. Len, Tetrahedron 2009,
65, 10105; e) E. Merino, Chem. Soc. Rev. 2011, 40, 3835; f) H. A.
Dabbagh, A. Teimouri, A. N. Chermahini, Dyes Pigm. 2007, 73, 239; g)
M. Barbero, S. Cadamuro, S. Dughera, C. Giaveno, Eur. J. Org. Chem.
2006, 4884.
[3]
[4]
a) G. V. Teplyakov, L. I. Blyakhman, A. M. Yakubson, J. Appl. Chem.
1982, 55, 1431; b) R. Zhao, C. Tan, Y. Xie, C. Gao, H. Liu, Y. Jiang,
Tetrahedron Lett. 2011, 52, 3805.
a) R. G. Anderson, G. Nickless, Analyst 1967, 92, 207; b) R. D. Athey,
Jr., Eur. Coatings J. 1998, 3, 146; c) D. M. Burland, R. D. Miller, C. A.
Walsh, Chem. Rev. 1994, 94, 31; d) A. J. Harvey, A. D. Abell,
Tetrahedron 2000, 56, 9763; e) W. J. Sandborn, Am. J. Gastroenterol.
2002, 97, 2939; f) K. Hunger, Industrial Dyes. Chemistry, Properties,
Applications, Wiley-VCH, Weinheim, 2003; g) E. Ishow, C. Bellaiche, L.
Bouteiller, K. Nakatani, J. A. Delaire, J. Am. Chem. Soc. 2003, 125,
15744; h) A. Bafana, S. S. Devi, T. Chakrabarti, Environ. Rev. 2011, 19,
For internal use, please do not delete. Submitted_Manuscript
This article is protected by copyright. All rights reserved.