Communication
ChemComm
5 (a) Q. Q. Cheng, S.-F. Zhu, Y.-Z. Zhang, X.-L. Xie and Q.-L. Zhou,
J. Am. Chem. Soc., 2013, 135, 14094–14097; (b) X. Li and D. P. Curran,
J. Am. Chem. Soc., 2013, 135, 12076–12081; (c) Q.-Q. Cheng, H. Xu,
S.-F. Zhu and Q.-L. Zhou, Acta Chim. Sin., 2015, 73, 326–329; (d) D. Chen,
X. Zhang, W.-Y. Qi, B. Xu and M.-H. Xu, J. Am. Chem. Soc., 2015, 137,
5268–5271; (e) J.-M. Yang, Z.-Q. Li and S.-F. Zhu, Chin. J. Org. Chem., 2017,
37, 2481–2497; ( f ) T. H. Allen, T. Kawamoto, S. Gardner, S. J. Geib and
D. P. Curran, Org. Lett., 2017, 19, 3680–3683; (g) S. B. J. Kan, X. Huang,
Y. Gumulya, K. Chen and F. H. Arnold, Nature, 2017, 552, 132–136.
6 J.-M. Yang, Y.-T. Zhao, Z.-Q. Li, X.-S. Gu, S.-F. Zhu and Q.-L. Zhou,
ACS Catal., 2018, 8, 7351–7355.
7 (a) J. E. Radcliffe, V. Fasano, R. W. Adams, P. You and M. J. Ingleson,
Chem. Sci., 2019, 10, 1434–1441; (b) S.-C. Ren, F.-L. Zhang, A.-Q. Xu,
Y. Yang, M. Zheng, X. Zhou, Y. Fu and Y.-F. Wang, Nat. Commun.,
2019, 10, 1934–1943; (c) W. Dai, S. J. Geib and D. P. Curran, J. Am.
Chem. Soc., 2019, 141, 12355–12361.
drug molecules. Synthetic application of the products was demon-
strated. Considering the great importance of a-borylcarbonyl com-
pounds in synthetic chemistry, we believe that this transformation
should have broad application prospects.
This work was supported by the Guangzhou key laboratory
of construction and application of new drug screening model
systems (Grant No. 201805010006), the key laboratory of new
drug discovery and evaluation of ordinary universities of
Guangdong province (Grant No. 2017KSYS002), a Start-up
Grant from Guangdong Pharmaceutical University (Grant No.
51377002), the Youth Innovation Talents Project of Colleges
and Universities in Guangdong Province (Grant No. 51377201),
and the Natural Science Foundation of Hunan Province (Grant
No. 12019JJ60071). The authors thank Dr Jia-Qiang Wu in Wuyi
University for helpful discussions.
8 For selected reviews, see: (a) X. Wu, S. Sun, J.-T. Yu and J. Cheng,
Synlett, 2019, 21–29; (b) J. Vaitla and A. Bayer, Synthesis, 2019,
612–628.
9 (a) Y. Xu, X. Yang, X. Zhou, L. Kong and X. Li, Org. Lett., 2017, 19,
4307–4310; (b) M. Barday, C. Janot, N. R. Halcovitch, J. Muir and
¨
C. Aıssa, Angew. Chem., Int. Ed., 2017, 56, 13117–13121; (c) X. Wu,
H. Xiong, S. Sun and J. Cheng, Org. Lett., 2018, 20, 1396–1399;
(d) C. Zhou, F. Fang, Y. Cheng, Y. Li, H. Liu and Y. Zhou, Adv. Synth.
Catal., 2018, 360, 2546–2551; (e) Y. Xu, G. Zheng, X. Yang and X. Li,
Chem. Commun., 2018, 54, 670–673; ( f ) K. S. Halskov, M. R. Witten,
G. L. Hoang, B. Q. Mercado and J. A. Ellman, Org. Lett., 2018, 20,
2464–2467.
Conflicts of interest
There are no conflicts to declare.
Notes and references
10 (a) I. K. Mangion, I. K. Nwamba, M. Shevlin and M. A. Huffman, Org.
Lett., 2009, 11, 3566–3569; (b) R. M. P. Dias and A. C. B. Burtoloso, Org.
Lett., 2016, 18, 3034–3037; (c) G. Chen, X. Zhang, R. Jia, B. Li and X. Fan,
Adv. Synth. Catal., 2018, 360, 3781–3787; (d) X. Wu, Y. Xiao, S. Sun,
J.-T. Yu and J. Cheng, Org. Lett., 2019, 21, 6653–6657; (e) X. Chen,
M. Wang, X. Zhang and X. Fan, Org. Lett., 2019, 21, 2541–2545.
1 (a) D. G. Hall, Boronic Acids, Wiley-VCH, Weinheim, Germany, 2005;
(b) Boronic Acids: Preparation and Applications in Organic Synth-
esis, in Medicine and Materials, ed. D. G. Hall, Wiley-VCH, New York,
2011; (c) H. Wang, C. Grohmann, C. Nimphius and F. Glorius, J. Am.
Chem. Soc., 2012, 134, 19592–19595; (d) S. Hyde, J. Veliks,
´
B. Liegault, D. Grassi, M. Taillefer and V. Gouverneur, Angew. Chem., 11 (a) M. Suleman, Z. Li, P. Lu and Y. Wang, Eur. J. Org. Chem., 2019,
Int. Ed., 2016, 55, 3785–3789; (e) J.-M. Yang, Z.-Q. Li, M.-L. Li, Q. He,
S.-F. Zhu and Q.-L. Zhou, J. Am. Chem. Soc., 2017, 139, 3784–3789;
( f ) J. Wu, P. Lorenzo, S. Zhong, M. Ali, C. P. Butts, E. L. Myers and
V. K. Aggarwal, Nature, 2017, 547, 436–440; (g) S.-C. Ren, F.-L.
Zhang, J. Qi, Y.-S. Huang, A.-Q. Xu, H.-Y. Yan and Y.-F. Wang,
J. Am. Chem. Soc., 2017, 139, 6050–6053; (h) Y.-F. Zeng, W.-W. Ji,
W.-X. Lv, Y. Chen, D.-H. Tan, Q. Li and H. Wang, Angew. Chem., Int.
Ed., 2017, 56, 14707–14711; (i) Y. Pang, Q. He, Z.-Q. Li, J.-M. Yang,
4447–4456; (b) Z. Tang, Y. Zhou and Q. Song, Org. Lett., 2019, 21,
5273–5276; (c) P. Chen, J. Nan, Y. Hu, Q. Ma and Y. Ma, Org. Lett.,
2019, 21, 4812–4815; (d) S. Wen, W. Lv, D. Ba, J. Liu and G. Cheng,
Chem. Sci., 2019, 10, 9104–9108; (e) D. Clare, B. C. Dobson,
¨
P. A. Inglesby and C. Aıssa, Angew. Chem., Int. Ed., 2019, 58,
16198–16202; ( f ) P. Wang, Y. Xu, J. Sun and X. Li, Org. Lett., 2019,
21, 8459–8463; (g) S. Hu, S. Du, Z. Yang, L. Ni and Z. Chen, Adv.
Synth. Catal., 2019, 361, 3124–3136.
J.-H. Yu, S.-F. Zhu and Q.-L. Zhou, J. Am. Chem. Soc., 2018, 140, 12 J. D. Neuhaus, A. Bauer, A. Pinto and N. Maulide, Angew. Chem., Int.
10663–10668; ( j) A. Zeineddine, F. Rekhroukh, E. D. S. Carrizo, Ed., 2018, 57, 16215–16218.
S. Mallet-Ladeira, K. Miqueu, A. Amgoune and D. Bourissou, Angew. 13 (a) A. G. Talero, B. S. Martins and A. C. B. Burtoloso, Org. Lett., 2018,
Chem., Int. Ed., 2018, 57, 1306–1310; (k) H. Wang, Y.-F. Zeng,
W.-X. Lv and D.-H. Tan, Synlett, 2018, 1415–1420; (l) D.-H. Tan,
Y.-H. Cai, Y.-F. Zeng, W.-X. Lv, L. Yang, Q. Li and H. Wang, Angew.
Chem., Int. Ed., 2019, 56, 14707–14711; (m) J. Lv, X. Chen, X.-S. Xue,
B. Zhao, Y. Liang, M. Wang, L. Jin, Y. Yuan, Y. Han, Y. Zhao, Y. Lu,
J. Zhao, W.-Y. Sun, K. N. Houk and Z. Shi, Nature, 2019, 575,
20, 7206–7211; (b) Y. Yuan and X.-F. Wu, Org. Lett., 2019, 21,
5310–5314; (c) H. Jiang, H. Zhang, W. Xiong, C. Qi, W. Wu,
L. Wang and R. Cheng, Org. Lett., 2019, 21, 1125–1129; (d) C. Li,
M. Li, W. Zhong, Y. Jin, J. Li, W. Wu and H. Jiang, Org. Lett., 2019,
21, 872–875; (e) C. Janot, P. Palamini, B. C. Dobson, J. Muir and
¨
C. Aıssa, Org. Lett., 2019, 21, 296–299.
336–340; (n) D. Kaiser, A. Noble, V. Fasano and V. K. Aggarwal, 14 Note: when we are preparing the manuscript, a very closely related
J. Am. Chem. Soc., 2019, 141, 14104–14109; (o) A. Fawcett, T. Biberger
and V. K. Aggarwal, Nat. Chem., 2019, 11, 117–122.
work was reported by Wu group. See: J. Li, H. He, M. Huang, Y. Chen,
Y. Luo, K. Yan, Q. Wang and Y. Wu, Org. Lett., 2019, 21, 9005–9008.
2 For reviews, see: (a) Z. He, A. Zajdlik and A. K. Yudin, Acc. Chem. 15 Y. Yang and S. L. Buchwald, Angew. Chem., Int. Ed., 2014, 53,
Res., 2014, 47, 1029–1040; (b) Z. He, A. Zajdlik and A. K. Yudin,
Dalton Trans., 2014, 43, 11434–11451.
8677–8681.
16 K. Yang and Q. Song, Green Chem., 2016, 18, 932–936.
3 E. W. H. Ng, K.-H. Low and P. Chiu, J. Am. Chem. Soc., 2018, 140, 17 R. J. Armstrong, W. Niwetmarin and V. K. Aggarwal, Org. Lett., 2017,
3537–3541. 19, 2762–2765.
4 (a) Z. He and A. K. Yudin, J. Am. Chem. Soc., 2011, 133, 13770–13773; 18 (a) Y. Xu, X. Zhou, G. Zheng and X. Li, Org. Lett., 2017, 19,
(b) J. Li and M. D. Burke, J. Am. Chem. Soc., 2011, 133, 13774–13777;
(c) W.-X. Lv, Y.-F. Zeng, Q. Li, Y. Chen, D.-H. Tan, L. Yang and
H. Wang, Angew. Chem., Int. Ed., 2016, 55, 10069–10073.
5256–5259; (b) J. Vaitla, A. Bayer and K. H. Hopmann, Angew. Chem.,
Int. Ed., 2017, 56, 4277–4281; (c) Y.-Y. Xing, J.-B. Liu, C.-Z. Sun,
F. Huang and D.-Z. Chen, J. Org. Chem., 2018, 83, 4545–4553.
Chem. Commun.
This journal is ©The Royal Society of Chemistry 2019