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RSC Advances
DOI: 10.1039/C6RA24144A
COMMUNICATION
Journal Name
6
L6
99.9
conditions: S/C=1000, [Rh]=2.12
3.5
92.9 3.6
10 mol/L, Toluene:3 mL, 5 Mpa,
7
(a) Y. Yan, X. Zhang and X. Zhang, Adv. Synth. Catal., 2007,
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Zhang, Chem. Eur. J., 2010,16, 4938; (d) S. Yu, Y. Chie, Z.
Guan and X. Zhang, Org. Lett., 2008, 10, 3469;
a
-3
×
00 C, 9 h; The conversion of DCPD based on GC; Selectivity for
o
b
c
1
TCDMA or TCDDA; See table 3.
d
tioned above. In contrast, L5 and L6 were of medium steric
hindrance, as a result, their rhodium complex might be less
crowded, thereby good selectivity was obtained by using L5
8
9
(a) C. Chen, Y. Qiao, H. Geng and X. Zhang, Org. Lett., 2013,
1
Wang, H. Lv, and X. Zhang, Org. Chem. Front., 2014, , 947.
5, 1048; (b) C. Chen, P. Li, Z. Hu, H. Wang, H. Zhu, X. Hu, Y.
1
(89.1%) and L6 (92.9%).
(a) M. Feller, Y. Diskin-Posner, L. J. W. Shimon, E. Ben-Ari and
D. Milstein. Organometallics, 2012, 31, 4083; (b) B. Vabre, M.
L. Lambert, A. Petit, D. H. Ess and D. Zargarian, Organo-
metallics, 2012, 31, 6041; (c) W. C. Shih andO. V. Ozerov,
Organometallics, 2015, 34, 459; (d) A. J. Kosanorich, J. H.
In summary, as for the difficult substrates like cyclohexene,
NBD and DCPD, the demand for a simultaneous increase in
mono- or di-) aldehyde selectivity and activity can be satisfied
(
by the L1/Rh system. The performance of L2/Rh system in cycl-
ohexene and NBD could be comparable with L1/Rh at lower
P/Rh molar ratio (5 vs 20), probably attributed to the more
stereo-hindered structural feature, which might also be the re-
ason that L2/Rh system exhibited relatively lower selectivity to
TCDDA in the hydroformylation of bulky DCPD. Owing to the
weaker π-acceptor ability of L3 (vs L1) and less steric hindrance
Reibenspies and O. V. Ozerov, Organometallics, 2016, 35,
13; (e) S. D. Timpa, C. J. Pell and O. V. Ozerov, J. Am. Chem.
Soc., 2014, 136, 14772; (f) H. A. Younus, N. Ahmad, W. Su
and F. Verpoort, Coord. Chem. Rev., 2014, 276, 112; (g) H. A.
Younus, W. Su, N. Ahmad, S. Chen, F. Verpoort. Adv. Synth.
Catal., 2015, 357,283.
0 (a) R. Cohen, M. E. van der Boom, L. J. W. Shimon, H. Ro-
zenberg and D. Milstein. J. Am. Chem. Soc., 2000, 122, 7723;
(b) M.E. Van der Boom and D. Milstein, Chem. Rev., 2003,
5
1
1
(vs L2), as well as the three coordination sites (P, P, N) of L4, L2
1
03, 1759; (c) M. Vogt, A. Nerush, M. A. Iron, G. Leitus, Y.
and L4 gave inferior performance in the hydroformylation of
these substrates. In comparison, L5 and L6 were likely of
medium steric hindrance and afforded good results with
medial P/Rh ratio, except for lower selectivity to dialdehyde in
Diskin-Posner, L. J. W. Shimon, Y. Ben-David, and D. Milstein,
J. Am. Chem. Soc., 2013, 135, 17004.
1 (a) J. Zhang, E. Balaraman, G. Leitus and D. Milstein, Organo-
metallics, 2011, 30, 5716.
NBD made by L5. These results enable the L1/Rh system to be 12 (a) J. Yao, W. T. Wong and G. Jia, J. Organomet. Chem., 2000,
5
98, 228; (b) A. Alzamly, S. Gambarotta and I. Korobkov. Org-
a potential candidate for the hydroformylation of cycloolefins.
anometallics, 2013, 32, 7204; (c) S. Sarkar, K. P. McGowan, S.
Kuppuswamy, I. Ghiviriga, K. A. Abboud and A. S. Veige, J.
Am. Chem. Soc., 2012, 134, 4509; (d) L. Luconi, J. Klosin, A. J.
Smith, S. Germain, E. Schulz, J. Hannedouche, and G. Giam-
bastiani, Dalton Trans., 2013, 42, 16056; (e) L. Chen, P. Ai, J.
Gu, S. Jie and B. G. Li, J. Organomet. Chem., 2012, 716, 55.
3 (a) K. G. Moloy and J. L. Petersen, J. Am. Chem. Soc., 1995,
The authors thank the financial support from the National
Natural Science Foundation of China (No. 201202108), from
the Opening Project of Key Laboratory of Green Chemistry of
Sichuan Institutes of Higher Education (No. LZJ1402), and from
the Sichuan university outstanding scholar research fund (No.
2015SCU04A05)
1
Notes and references
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