Citation: SUN Yan, LIU Rui-Ting, WENG Lin-Hong, ZHOU Xi-Geng. Syntheses, Cycloaminocarbonylation and Amidination of Rare Earth o-Aminobenzamido Dianion Complexes Bearing Cyclopentadienyl Co-ligand[J]. Chinese Journal of Inorganic Chemistry, ;2017, 33(11): 2124-2138. doi: 10.11862/CJIC.2017.255 shu

Syntheses, Cycloaminocarbonylation and Amidination of Rare Earth o-Aminobenzamido Dianion Complexes Bearing Cyclopentadienyl Co-ligand

1.
Department of Chemistry, Shanghai Key Laboratory of Molecular Catalysis and Innovative Materials, Fudan University, Shanghai 200433, China
2.
State Key Laboratory of Organometallic Chemistry, Shanghai 200032, China

Corresponding author: ZHOU Xi-Geng, xgzhou@fudan.edu.cn
Received Date: 1 September 2017
Revised Date: 22 September 2017

Figures(11)

Treatment of Cp₃Ln with o-aminobenzamide followed by crystallization in a HMPA and toluene mixture affords the tetranuclear organolanthanide complexes [CpLn(μ-η²:η²-NHC₆H₄CONH)(μ₃-η¹:η¹:η²-NHC₆H₄CONH)LnCp(HMPA)}₂ (Ln=Yb, 1a; Er, 1b; Y, 1c). Reaction of 1 with PhNCO (n_PhNCO/n₁=4) in toluene gives the dianionic quinazolyldiolate (Quo) complexes [Cp₂Ln(μ₃-η²:η²:η¹-Quo)]₃Ln(HMPA)₂ (Ln=Yb, 2a; Er, 2b; Y, 2c), indicating that one isocyanate molecule can undergo the tandem reaction with both NH and CONH of 1 to construct a quinazoly-ldiolate skeleton, companying with the elimination of PhNH₂. However, 1a~1c react with ⁱPrN=C=NⁱPr under the same conditions to give only the single ArNH addition products {Cp₂Ln[μ-η¹:η¹:η²-ⁱPrNC(NHⁱPr)NC₆H₄ CONH]}₃Ln(HMPA)₃ (Ln=Yb, 3a; Er, 3b; Y, 3c). Furthermore, treatment of Cp₃Ln with o-aminobenzamide followed by reacting with ⁱPrN=C=NⁱPr gave {CpLn[μ-η¹:η²:η²-NHCOC₆H₄NC(NHⁱPr)NⁱPr]}₂ (Ln=Yb, 4a; Er, 4b; Y, 4c). Noticeably, HMPA could induce the transformation of 4 into 3 by a ligand redistribution.
- lanthanide complexes,
- cycloaminocarbonylation,
- isocyanate,
- o-aminobenzamide,
- addition
1. [1]
  (a) Molander G A, Romero J A C. Chem. Rev., 2002, 102(6): 2161-2185
  (b)Muller T E, Hultzsch K C, Yus M. Chem. Rev., 2008, 108 (9): 3795-3892
  (c)Bartoli G, Marcantoni E, Marcolini M, et al. Chem. Rev., 2010, 110(10): 6104-6143
  (d)Zeng X M. Chem. Rev., 2013, 113(8): 6864-6900
2. [2]
  (a) Evans W J, Davis B L. Chem. Rev., 2002, 102(6): 2119-2136
  (b)Zhou X G, Zhu M. J. Organomet. Chem., 2002, 647(1/2): 28-49
  (c)Hong S, Marks T J. Acc. Chem. Res., 2004, 37(9): 673-686
  (d)Zhang J, Zhou X G. Dalton Trans., 2011, 40(38): 9637-9648
  (e)Liu R T, Zhou X G. Chem. Commun., 2013, 49(31): 3171-3187
3. [3]
  (a) Jeske G, Lauke H, Mauermann H, et al. J. Am. Chem. Soc., 1985, 107(26): 8091-8103
  (b)Cui D M, Nishiura M, Hou Z M. Angew. Chem. Int. Ed., 2005, 44(6): 959-962
  (c)Wang B L, Wang D, Cui D M, et al. Organometallics, 2007, 26(13): 3167-3172
  (d)Kaneko H, Nagae H, Tsurugi H, et al. J. Am. Chem. Soc., 2011, 133(49): 19626-19629
  (e)Zhou S L, Wang H Y, Ping J, et al. Organometallics, 2012, 31(5): 1696-1702
  (f)Hong L C, Lin W J, Zhou X G, et al. Chem. Commun., 2013, 49(49): 5589-5591
4. [4]
  (a) Li W B, Xue M Q, Xu F, et al. Dalton Trans., 2012, 41(27): 8252-8260
  (b)Basalov I V, Lyubov D M, Fukin G K, et al. Angew. Chem. Int. Ed., 2012, 51(14): 3444-3447
  (c)Sun J L, Berg D J, Twamley B. Organometallics, 2008, 27 (4): 683-690
  (d)Yang Y, Cui D M, Chen X S. Dalton Trans., 2010, 39(16): 3959-3967
  (e)Li X Q, Hong J Q, Zhou X G, et al. Organometallics, 2010, 29(20): 4606-4610
  (f)Pi C F, Li X Q, Zhang L L, et al. Inorg. Chem., 2010, 49 (17): 7632-7634
  (g)Zhang Z X, Bu X L, Zhang J, et al. Organometallics, 2010, 29(9): 2111-2117
  (h)Lu E L, Chen Y F, Leng X B. Organometallics, 2011, 30 (20): 5433-5441
  (i)Casely I J, Ziller J W, Evans W J. Organometallics, 2011, 30(18): 4873-4881
5. [5]
  (a) Liu R T, Zhang C M, Zhu Z Y, et al. Chem. Eur. J., 2006, 12 (26): 6940-6952
  (b)Li X Q, Liu R T, Zhang Z X, et al. Organometallics, 2010, 29(15): 3298-3302
  (c)Chu J X, Lu E L, Liu Z X, et al. Angew. Chem. Int. Ed., 2011, 50(33): 7677-7680
  (d)Shao Y L, Zhang F J, Zhang J, et al. Angew. Chem. Int. Ed., 2016, 55(38): 11485-11489
  (e)Hong J Q, Li Z H, Chen Z N, et al. Dalton Trans., 2016, 45(15): 6641-6649
  (f)Huang S J, Shao Y L, Zhang L X, et al. Angew. Chem. Int. Ed., 2015, 54(48): 14452-14456
  (g)Luo Y, Teng H L, Nishiura M, et al. Angew. Chem. Int. Ed., 2017, 56(31): 9207-9210
6. [6]
  (a) Yasuda H, Yamamoto H, Yokota K, et al. J. Am. Chem. Soc., 1992, 114(12): 4908-4910
  (b)Giardello M A, Yamamoto Y, Brard L, et al. J. Am. Chem. Soc., 1995, 117(11): 3276-3277
  (c)Zhang W X, Nishiura M, Hou Z M. Angew. Chem. Int. Ed., 2008, 47(50): 9700-9703
  (d)Yang J Y, Shen H, Xie Z W. J. Organomet. Chem., 2015, 798: 204-208
  (e)Xu L, Zhai M K, Wang F, et al. Dalton Trans., 2016, 45 (43): 17108-17112
  (f)Song G Y, Wang B L, Nishiura M, et al. Chem. Eur. J., 2015, 21(23): 8394-8398
  (g)Xu P F, Yao Y M, Xu X. Chem. Eur. J., 2017, 23(6): 1263-1267
7. [7]
  (a) Molander G A, Romero J A C. Chem. Rev., 2002, 102(6): 2161-2185
  (b)Konkol M, Kondracka M, Voth P, et al. Organometallics, 2008, 27(15): 3774-3784
  (c)Ohashi M, Konkol M, Rosal D, et al. J. Am. Chem. Soc., 2008, 130(22): 6920-6921
  (d)Barros N, Eisenstein O, Maron L. Dalton Trans., 2010, 39 (44): 10757-10767
  (e)Abinet E, Spaniol T P, Okuda J. Chem. Asian J., 2011, 6 (2): 389-391
8. [8]
  (a) Lauterwasser F, Hayes P G, Piers W E, et al. Adv. Synth. Catal., 2011, 353(8): 1384-1390
  (b)Zhang Y Y, Yao W, Li H, et al. Organometallics, 2012, 31 (13): 4670-4679
  (c)Trambitas A G, Melcher D, Hartenstein L, et al. Inorg. Chem., 2012, 51(12): 6753-6761
  (d)Reznichenko A L, Hultzsch K C. Organometallics, 2013, 32(5): 1394-1408
  (e)Huang S J, Shao Y L, Zhang L X, et al. Angew. Chem. Int. Ed., 2015, 54(48): 14452-14456
  (f)Hong S, Marks T J. Acc. Chem. Res., 2004, 37(9): 673-686
9. [9]
  (a) Yu X H, Seo S Y, Marks T J. J. Am. Chem. Soc., 2007, 129(23): 7244-7245
  (b)Seo S Y, Yu X H, Marks T J. J. Am. Chem. Soc., 2009, 131(1): 263-276
10. [10]
  (a) Weiss C J, Marks T J. Dalton Trans., 2010, 39: 6576-6588
  (b)Weiss C J, Wobser S D, Marks T J. Organometallics, 2010, 29(23): 6308-6320
11. [11]
  (a) Douglass M R, Stern C L, Marks T J. J. Am. Chem. Soc., 2001, 123(42): 10221-10238
  (b)Takaki K, Koshoji G, Komeyama K, et al. J. Org. Chem., 2003, 68(17): 6554-6565
  (c)Kawaoka A M, Marks T J. J. Am. Chem. Soc., 2004, 126 (40): 12764-12765
  (d)Hu H F, Cui C M. Organometallics, 2012, 31(3): 1208-1211
  (e)Behrle A C, Schmidt J A R. Organometallics, 2013, 32(5): 1141-1149
12. [12]
  (a) Hung S C, Wen Y F, Chang J W, et al. J. Org. Chem., 2002, 67(4): 1308-1313
  (b)Schumann H, Heim A, Demtschuk J, et al. Organometallics, 2003, 22(1): 118-128
  (c)Yuan Y Y, Wang X F, Li Y X, et al. Organometallics, 2011, 30(16): 4330-4341
13. [13]
  (a) Guan B T, Hou Z M. J. Am. Chem. Soc., 2011, 133(45): 18086-18089
  (b)Oyamada J, Hou Z M. Angew. Chem. Int. Ed., 2012, 51: 12828-12832
  (c)Guan B T, Wang B L, Nishiura M, et al. Angew. Chem. Int. Ed., 2013, 52: 4418-4421
  (d)Shi X C, Nishiura M, Hou Z M. J. Am. Chem. Soc., 2016, 138: 61476150
  (e)Arnold P L, McMullon M W, Rieb J, et al. Angew. Chem. Int. Ed., 2015, 55: 82-100
14. [14]
  (a) Monsaert S, Vila A L, Drozdzak R, et al. Chem. Soc. Rev., 2009, 38: 3360-3372
  (b)Leitao E M, van der Eide E F, Romero P E, et al. J. Am. Chem. Soc., 2010, 132(8): 2784-2794
  (c)Woodward C P, Spiccia N D, Jackson W R, et al. Chem. Commun., 2011, 47: 779-781
15. [15]
  (a) Shima T, Hou Z M. J. Am. Chem. Soc., 2006, 128(25): 8124-8125
  (b)Zhou J L, Chu J X, Zhang Y Y, et al. Angew. Chem. Int. Ed., 2013, 52(15): 4243-4246
16. [16]
  (a) Zhang W X, Wang Z, Nishiura M, et al. J. Am. Chem. Soc., 2011, 133(15): 5712-5715
  (b)Hong J Q, Zhang L X, Yu X Y, et al. Chem. Eur. J., 2011, 17(7): 2130-2137
  (c)Hong J Q, Zhang L X, Wang K, et al. Chem. Eur. J., 2013, 19(24): 7865-7873
17. [17]
  (a) Masui H, Fuse S, Takahashi T. Org. Lett., 2012, 14(16): 4090-4093
  (b)Campbell M J, Toste F D. Chem. Sci., 2011, 2(7): 1369-1378
  (c)Attanasi O A, de Crescentini L, Favi G S. et al. Org. Lett., 2011, 13(3): 353-355
  (d)Groenendaal B, Vugts D J, Schmitz R F, et al. J. Org. Chem., 2008, 73(2): 719-722
  (e)Church T L, Byrne C M, Lobkovsky E B, et al. J. Am. Chem. Soc., 2007, 129(26): 8156-8162
18. [18]
  (a) Braunstein P, Nobel D. Chem. Rev., 1989, 89(8): 1927-1945
  (b)Kuninobu Y, Tokunaga Y, Kawata A, et al. J. Am. Chem. Soc., 2006, 128(1): 202-209
  (c)Paul F, Moulin S, Piechaczyk O, et al. J. Am. Chem. Soc., 2007, 129(23): 7294-7304
  (d)Zhu X C, Fan J X, Wu Y J, et al. Organometallics, 2009, 28 (13): 3882-3888
  (e)Sharpe H R, Geer A M, Williams H E L, et al. Chem. Commun., 2017, 53(5): 937-940
19. [19]
  (a) Evans W J, Forrestal K J, Ziller J W. J. Am. Chem. Soc., 1998, 120(36): 9273-9282
  (b)Shen Q, Li H R, Yao C S, et al. Organometallics, 2001, 20(14): 3070-3073
  (c)Shen Q, Yao Y M. J. Organomet. Chem., 2002, 647(1/2): 180-189
  (d)Han Y N, Zhang J, Han F Y, et al. Organometallics, 2009, 28(13): 3916-3921
  (e)Yi W Y, Zhang J, Li M, et al. Inorg. Chem., 2011, 50(22): 11813-11824
20. [20]
  (a) Zhang J, Ma L P, Cai R F, et al. Organometallics, 2005, 24(4): 738-742
  (b)Du Z, Zhou H, Yao H, et al. Chem. Commun., 2011, 47 (12): 3595-3597
21. [21]
  Tardif O, Hashizume D, Hou Z M. J. Am. Chem. Soc., 2004, 126(26):8080-8081 doi: 10.1021/ja047889u
22. [22]
  Qian C T, Ye C Q, Lu H Z, et al. J. Organomet. Chem., 1983, 247(2):161-170 doi: 10.1016/S0022-328X(00)98751-5
23. [23]
  SAINTPlus, Data Reduction and Correction Program Ver. 6. 02a, Bruker AXS, Madison, WI, 2000.
24. [24]
  Sheldrick G M. SADABS, A Program for Empirical Absorption Correction, University of Göttingen, Germany, 1998.
25. [25]
  Sheldrick G M. SHELXL-97, Program for the Refinement of Crystal Structures, University of Göttingen, Germany, 1997.
26. [26]
  (a) Sun Y, Zhang Z X, Wang X, et al. Organometallics, 2009, 28(21): 6320-6330
  (b)Sun Y, Zhang Z X, Wang X, et al. Dalton Trans., 2010, 39(1): 221-226
  (c)Zhang J, Han Y N, Han F Y, et al. Inorg. Chem., 2008, 47(13): 5552-5554
27. [27]
  (a) Pi C F, Liu R T, Zheng P Z, et al. Inorg. Chem., 2007, 46 (13): 5252-5259
  (b)Pi C F, Zhu Z Y, Weng L H, et al. Chem. Commun., 2007 (21): 2190-2192
  (c)Pi C F, Zhang Z X, Pang Z, et al. Organometallics, 2007, 26(8): 1934-1946
28. [28]
  (a) Evans W J, Ulibarri T A, Chamberlain L R, et al. Orga-nometallics, 1990, 9(7): 2124-2130
  (b)Evans W J, Foster S E. J. Organomet. Chem., 1992, 433 (1/2): 79-94
  (c)Venugopal A, Kamps I, Bojer D, et al. Dalton Trans., 2009(29): 5755-5765
29. [29]
  (a) Willis M C, Snell R H, Fletcher A J, et al. Org. Lett., 2006, 8(22): 5089-5091
  (b)Vorbrueggen H, Krolikiewicz K. Tetrahedron, 1994, 50 (22): 6549-6558
  (c)Li J R, Chen X A, Shi D X, et al. Org. Lett., 2009, 11(6): 1193-1196
  (d)Patil Y P, Tambade P J, Deshmukh K M, et al. Catal. Today, 2009, 148(3/4): 355-360
30. [30]
  Zhou X G, Huang Z E, Cai R F, et al. J. Organomet. Chem., 1998, 563(1/2):101-112
31. [31]
  Allen F H, Kennard O, Watson D G, et al. J. Chem. Soc., Perkin Trans., 1987(12):S1-S19 doi: 10.1039/p298700ba001
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