10.1002/cctc.201801525
ChemCatChem
FULL PAPER
mesitylene for 1,2-diphenylethane-1,2-diol) (3 mL) were added. The
resulting solution was stirred at 110 °C (or 130 °C for aliphatic alcohols
and 4-chlorobenzene-1,2-diamine, 150 °C for 1,2-diphenylethane-1,2-
diol) for 24 h. After cooling to room temperature, the catalyst was
separated by filtration and washed with ethyl acetate and water. The
filtrate was extracted three times with ethyl acetate (3 × 5 mL). The
combined organic layers were washed with brine, dried over anhydrous
Na2SO4 and concentrated under reduced pressure. The crude product
was purified by flash column chromatography using petroleum ether and
ethyl acetate as the eluent.
Sci. Technol. 2015, 5, 1412-1427; j) S. M. A. H. Siddiki, T. Toyao, K.
Shimizu, Green Chem. 2018, 20, 2933-2952.
[7]
[8]
a) A. Corma, J. Navas, M. J. Sabater, Chem. Rev. 2018, 118,
1410−1459; b) T. D. Nixon, M. K. Whittlesey, J. M. J. Williams, Dalton
Trans. 2009, 753-762; c) H. Wu, J. Wu, Z. Du, Chin. J. Org. Chem.
2017, 37, 1127-1138.
a) B. Gnanaprakasam, J. Zhang, D. Milstein, Angew. Chem. Int. Ed.
2010, 49, 1468-1471; b) B. Gnanaprakasam, E. Balaraman, Y. Ben-
David, D. Milstein, Angew. Chem. Int. Ed. 2011, 50, 12240-12244. c) P.
Hu, Y. Ben-David, D. Milstein, Angew. Chem. Int. Ed. 2016, 55, 1061-
1064; d) R. Cano, D. J. Ramón, M. Yus, J. Org. Chem. 2011, 76, 5547-
5557; e) S. Demir, F. Coşkun, Ì. Özdemir, J. Organomet. Chem. 2014,
755, 134-140; f) F. E. Fernández, M. C. Puerta, P. Valerga,
Organometallics 2012, 31, 6868-6879; g) D. Srimani, Y. Ben-David, D.
Milstein, Angew. Chem. Int. Ed. 2013, 52, 4012-4015.
Acknowledgements
This work was financially supported by the National Natural
Science Foundation of China (Grant Nos. 21471108, 21771131,
21531006 and 21773163), the State Key Laboratory of
Organometallic Chemistry of Shanghai Institute of Organic
Chemistry (2015kf-07), the Priority Academic Program
Development of Jiangsu Higher Education Institutions, the
Natural Science Foundation of Jiangsu Province (BK20161276)
and the Project of Scientific and Technologic Infrastructure of
Suzhou (SZS201708). We are very grateful to the useful
comments and suggestions of the editor and reviewers.
[9]
a) S. Michlik, R. Kempe, Nat. Chem. 2013, 5, 140-144; b) J. Schranck,
A. Tlili, M. Beller, Angew. Chem. Int. Ed. 2013, 52, 7642-7644; c) K.
Iida, T. Miura, J. Ando, S. Saito, Org. Lett. 2013, 15, 1436-1439; d) P.
Daw, S. Chakraborty, J. A. Garg, Y. Ben-David, D. Milstein, Angew.
Chem. Int. Ed. 2016, 55, 14373-14377; e) M. Zhang, X. J. Fang, H.
Neumann, M. Beller, J. Am. Chem. Soc. 2013, 135, 11384-11388.
[10] D. Srimani, Y. Ben-David, D. Milstein, Chem. Commun. 2013, 49, 6632-
6634.
[11] a) R. Ramachandran, G. Prakash, S. Selvamurugan, P.
Viswanathamurthi, J. G. Malecki, V. Ramkumar, Dalton Trans. 2014, 43,
7889-7902; b) M. Bala, P. K. Verma, U. Sharma, N. Kumar, B. Singh,
Green Chem. 2013, 15, 1687-1693; c) T. Kondo, S. Yang, K. T. Huh, M.
Kobayashi, S. Kotachi, Y. Watanabe, Chem. Lett. 1991, 20, 1275-1278.
[12] a) M. O. Chaney, P. V. Demarco, N. D. Jones, J. L. Occolowitz, J. Am.
Chem. Soc. 1974, 96, 1932-1933; b) A. J. Battershill, L. Scott, J. Drugs
2006, 66, 51-83; c) Fungicidal Agents. Kirk-Othmer Encyclopedia of
Chemical Technology, Vol. 11, Wiley, New York, 1980, pp 490-498; d)
M. E. Mason, B. Johnson, M. Hamming, J. Agric. Food Chem. 1966, 14,
454-460; e) Y. Wang, G. A. Sotzing, R. A. Weiss, Chem. Mater. 2008,
20, 2574-2882.
Conflict of interest
The authors declare no conflict of interest.
Keywords: ADC reaction • ATH reaction • Recyclability •
[13] C. E. Song, S. G. Lee, Chem. Rev. 2002, 102, 3495-3524; b) Z. L. Lu,
E. Lindner, H. A. Mayer, Chem. Rev. 2002, 102, 3543-3578; c) M.
Lamblin, L. Nassar-Hardy, J. C. Hierso, E. Fouquet, F. X. Felpin, Adv.
Synth. Catal. 2010, 352, 33-79.
Ruthenium nanoparticles • Selectivity
[1]
[2]
a) M. B. Smith, J. March, Advanced Organic Chemistry, Wiley, New
York, 5th edn, 2001, pp. 499-501; b) R. N. Salvatore, C. H. Yoon, K. W.
Jung, Tetrahedron 2001, 57, 7785-7811.
[14] a) L. He, X. B. Lou, J. Ni, Y. M. Liu, Y. Cao, H. Y. He, K. N. Fan, Chem.
Eur. J. 2010, 16, 13965-13969; b) H. Liu, G. K. Chuah, S. Jaenicke, J.
Catal. 2012, 292, 130-137; c) K. Shimizu, N. Imaiida, K. Kon, S. M. A. H.
Siddiki, A. Satsuma, ACS Catal. 2013, 3, 998-1005; d) Y. Gao, J. Wang,
A. Han, S. Jaenicke, G. K. Chuah, Catal. Sci. Technol. 2016, 6, 3806-
3813; e) H. Yang, Y. Wang, Y. Qin, Y. Chong, Q. Yang, G. Li, L. Zhang,
W. Li, Green Chem. 2011, 13, 1352-1361.
a) K. H. Hopmanna, A. Bayer, Coord. Chem. Rev. 2014, 268, 59-82; b)
N. Fleury-Brégeot, V. Fuente, S. Castillón, C. Claver, ChemCatChem
2010, 2, 1346-1371; c) J. G. Vries, N. Mršic, Catal. Sci. Technol. 2011,
1, 727-735.
[3]
[4]
a) F. Alonso, P. Riente, M. Yus, Acc. Chem. Res. 2011, 44, 379-391; b)
C. F. Lane, Synthesis 1975, 135-146; c) G. W. Gribble, Chem. Soc.
Rev. 1998, 27, 395-404; d) A. F. Abdel-Magid, K. G. Carson, B. D.
Harris, C. A. Maryanoff, R. D. Shah, J. Org. Chem. 1996, 61, 3849-
3862; e) T. Gross, A. M. Seayad, M. Ahmad, M. Beller, Org. Lett. 2002,
4, 2055-2058; f) R. V. Jagadeesh, K. Murugesan, A. S. Alshammari, H.
Neumann, M. Pohl, J. Radnik, M. Beller, Science 2017, 358, 326-332.
a) J. F. Hartwig, Synlett 2006, 1283-1294; b) S. L. Buchwald, C.
Mauger, G. Mignani, U. Scholz, Adv. Synth. Catal. 2006, 348, 23-39; c)
O. Navarro, N. Marion, J. Mei, S. P. Nolan, Chem. Eur. J. 2006, 12,
5142-5148.
[15] S. Wittmann, A. Schätz, R. N. Grass, W. J. Stark, O. Reiser, Angew.
Chem. Int. Ed. 2010, 49, 1867-1870.
[16] a) E. R. Rangel, E. M. Maya, F. Sánchez, J. G. Campa, M. Iglesias,
Green Chem. 2015, 17, 466-473; b) E. Verde-Sesto, E. M. Maya, A. E.
Lozano, J. G. Campa, F. Sánchez, M. Iglesias, J. Mater. Chem. 2012,
22, 24637-24643; c) Q. Sun, Z. Dai, X. Meng, L. Wang, F. S. Xiao, ACS
Catal. 2015, 5, 4556-45671; d) N. B. McKeown, P. M. Budd, Chem. Soc.
Rev. 2006, 35, 675-683; e) E. Verde-Sesto, E. Merino, E. Rangel-
Rangel, A. Corma, M. Iglesias, F. Sánchez, ACS Sustainable Chem.
Eng. 2016, 4, 1078-1084; f) E. Rangel-Rangel, E. Verde-Sesto, A. M.
Rasero-Almansa, M. Iglesias, F. Sánchez, Catal. Sci. Technol. 2016, 6,
6037-6045.
[5]
[6]
a) G. E. Dobereiner, R. H. Crabtree, Chem. Rev. 2010, 110, 681-703;
b) M. H. S. A. Hamid, P. A. Slatford, J. M. J. Williams, Adv. Synth. Catal.
2007, 349, 1555-1575.
[17] a) C. D. Wu, A. Hu, L. Zhang, W. Lin, J. Am. Chem. Soc. 2005, 127,
8940-8941; b) F. Song, C. Wang, J. M. Falkowski, L. Ma, W. Lin, J. Am.
Chem. Soc. 2010, 132, 15390-15398; c) Y. Liu, W. Xuan, Y. Cui, Adv.
Mater. 2010, 22, 4112-4135; d) A. Arnanz, M. Pintado-Sierra, A. Corma,
M. Iglesias, F. Sánchez, Adv. Synth. Catal. 2012, 354, 1347-1355; e) M.
Pintado-Sierra, A. M. Rasero-Almansa, A. Corma, M. Iglesias, F.
Sánchez, J. Catal. 2013, 299, 137-145; f) A. M. Rasero-Almansa, A.
Corma, M. Iglesias, F. Sánchez, ChemCatChem 2013, 5, 3092-3100.
[18] A. Peeters, L. Claes, I. Geukens, I. Stassen, D. D. Vos, Appl. Catal. A
Gen. 2014, 469, 191-197.
a) C. Gunanathan, D. Milstein, Science 2013, 341, 249-260; b) M.
Zhang, H. Neumann, M. Beller, Angew. Chem. Int. Ed. 2013, 52, 597-
601; c) S. Michlik, R. Kempe, Angew. Chem. Int. Ed. 2013, 52, 6326-
6329; d) A. J. Blacker, M. M. Farah, M. I. Hall, S. P. Marsden, O. Saidi,
J. M. J. Williams, Org. Lett. 2009, 11, 2039-2042; e) K. Taguchi, S.
Sakaguchi, Y. Ishii, Tetrahedron Lett. 2005, 46, 4539-4542; f) F. Li, L.
Lu, P. C. Liu, Org. Lett. 2016, 18, 2580-2583; g) T. Hille, T. Irrgang, R.
Kempe, Chem. Eur. J. 2014, 20, 5569-5572; h) C. Gunanathan, Y. Ben-
David, D. Milstein, Science 2007, 317, 790-792; i) K. Shimizu, Catal.
9
This article is protected by copyright. All rights reserved.