Paper
Organic & Biomolecular Chemistry
resonance structure B with an electrophilic feature in the δ-
position. Next, Et3SiH as the nucleophile attacks the carbon
center of intermediate B to afford C, which gives the resulting
species D by releasing the uranyl catalyst. Finally, D goes
through hydrolysis in the presence of trace amounts of water
Z. F. Chai, T. E. Albrecht-Schmitt and S. Wang, J. Am. Chem.
Soc., 2015, 137, 6144–6147.
9 P. Li, N. A. Vermeulen, X. R. Gong, C. D. Malliakas,
J. F. Stoddart, J. T. Hupp and O. K. Farha, Angew. Chem.,
Int. Ed., 2016, 55, 10358–10362.
to deliver the target molecule 3a together with the generation 10 E. A. Dolgopolova, O. A. Ejegbaywo, C. R. Martin,
of Et3SiOH. Et3SiOH is further dehydrated to Et3SiOSiEt3.
M. D. Smith, W. Setyawan, S. G. Karakalos, C. H. Henager,
H. C. zur Loye and N. B. Shustova, J. Am. Chem. Soc., 2017,
139, 16852–16861.
11 P. Li, N. A. Vermeulen, C. D. Malliakas, D. A. Gomez-
Gualdron, A. J. Howarth, B. L. Mehdi, A. Dohnalkova,
N. D. Browning, M. O’Keeffe and O. K. Farha, Science, 2017,
356, 624–627.
Conclusions
In conclusion, we have developed a new example of a catalytic
transformation of readily available p-QMs using uranyl in the
presence of reductive silane at room temperature. This proto- 12 J. Xie, Y. X. Wang, W. Liu, X. M. Yin, L. H. Chen, Y. M. Zou,
col provides an efficient and practical method to synthesize
diarylmethane derivatives with broad substrate scope and
excellent functional group tolerance. The investigation of the
J. Diwu, Z. F. Chai, T. E. Albrecht-Schmitt, G. K. Liu and
S. A. Wang, Angew. Chem., Int. Ed., 2017, 56, 7500–
7504.
mechanism revealed that uranyl was acting as a powerful 13 Y. X. Wang, X. M. Yin, W. Liu, J. Xie, J. F. Chen,
Lewis acid catalyst for the hydrosilylation process. Further
applications of uranyl in organic synthesis are under investi-
gation in our lab.
M. A. Silver, D. P. Sheng, L. H. Chen, D. W. Juan, N. Liu,
Z. F. Chai, T. E. Albrecht-Schmitt and S. A. Wang, Angew.
Chem., Int. Ed., 2018, 57, 7883–7887.
14 H. D. Burrows and T. J. Kemp, Chem. Soc. Rev., 1974, 3,
139–165.
15 J. G. West, T. A. Bedell and E. J. Sorensen, Angew. Chem.,
Int. Ed., 2016, 55, 8923–8927.
Conflicts of interest
There are no conflicts to declare.
16 L. L. Wu, X. Y. Cao, X. B. Chen, W. H. Fang and M. Dolg,
Angew. Chem., Int. Ed., 2018, 57, 11812–11816.
17 L. Capaldo, D. Merli, M. Fagnoni and D. Ravelli, ACS Catal.,
2019, 9, 3054–3058.
18 T. Mashita, S. Tsushima and K. Takao, ACS Omega, 2019, 4,
7194–7199.
Acknowledgements
This work was supported by the National Science Fund for
Distinguished Young Scholars (No. 21925603), the National 19 P. L. Arnold, J. M. Purkis, R. Rutkauskaite, D. Kovacs,
Natural Science Foundation of China (No. 21806167), the
Science Challenge Project (TZ2016004), and the Youth
Innovation Promotion Association of CAS (2017020).
J. B. Love and J. Austin, ChemCatChem, 2019, 11, 3786–
3790.
20 V. V. Castelli, A. Dalla Cort, L. Mandolini, D. N. Reinhoudt
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