Citation: Jiasheng Qian, Zhi-Hao Chen, Yuan Liu, Yin Li, Qingjiang Li, Shi-Liang Huang, Honggen Wang. Synthesis of allenyl-B(MIDA) via hydrazination/fragmentation reaction of B(MIDA)-propargylic alcohol[J]. Chinese Chemical Letters, ;2023, 34(1): 107479. doi: 10.1016/j.cclet.2022.04.077 shu

Synthesis of allenyl-B(MIDA) via hydrazination/fragmentation reaction of B(MIDA)-propargylic alcohol

Guangdong Key Laboratory of Chiral Molecule and Drug Discovery, School of Pharmaceutical Sciences, Sun Yat-Sen University, Guangzhou 510006, China

lsshsl@mail.sysu.edu.cn

wanghg3@mail.sysu.edu.cn

Received Date: 29 March 2022
Revised Date: 26 April 2022
Accepted Date: 28 April 2022
Available Online: 5 May 2022

Figures(5)

Allenylboronates represent a very intriguing class of organoborons but are challenging to synthesis. In addition, these compounds are typically unstable, rendering the separation difficult. We report herein a practical and concise route to a new class of stable, easy-separable allenyl B(MIDA) via a hydrazination/fragmentation of B(MIDA)-propargylic alcohols. The synthesis of optically active allenyl B(MIDA) was also achieved. Interesting reactivity of the resulting product was observed.
- Allenyl boronate,
- Mitsunobu reaction,
- Mida boronates,
- Hydrazination,
- Fragmentation,
- Chirality transfer
1. [1]
  J.A. Marshall, J.Org. Chem.72 (2007) 8153–8166 doi: 10.1021/jo070787c
2. [2]
  D.S. Barnett, S.E. Schaus, Org. Lett. 13 (2011) 4020–4023 doi: 10.1021/ol201535b
3. [3]
  C.H. Ding, X.L. Hou, Chem. Rev. 111 (2011) 1914–1937 doi: 10.1021/cr100284m
4. [4]
  A.S. Tsai, M. Chen, W.R. Roush, Org. Lett. 15 (2013) 1568–1571 doi: 10.1021/ol4003459
5. [5]
  F. Liepouri, G. Bernasconi, N.A. Petasis, Org. Lett. 17 (2015) 1628–1631 doi: 10.1021/acs.orglett.5b00024
6. [6]
  S. Yu, S. Ma, Chem. Commun., 47 (2011) 5384–5418 doi: 10.1039/c0cc05640e
7. [7]
  S. Koyama, F. Takahashi, H. Saito, H. Yorimitsu, Org. Lett. 23 (2021) 8590–8594 doi: 10.1021/acs.orglett.1c03316
8. [8]
  Y. Matsumoto, M. Naito, T. Hayashi, Organometallics 11 (1992) 2732–2734 doi: 10.1021/om00043a075
9. [9]
  Y. Matsumoto, M. Naito, Y. Uozumi, T. Hayashi, J. Chem. Soc. Chem. Commun. (1993) 1468–1469
10. [10]
  D.W. Gao, Y. Xiao, M. Liu, et al., ACS Catal. 8 (2018) 3650–3654 doi: 10.1021/acscatal.8b00626
11. [11]
  Y. Huang, J. del Pozo, S. Torker, A.H. Hoveyda, J. Am. Chem. Soc. 140 (2018) 2643–2655 doi: 10.1021/jacs.7b13296
12. [12]
  H.L. Sang, S. Yu, S. Ge, Org. Chem. Front. 5 (2018) 1284–1287 doi: 10.1039/C8QO00167G
13. [13]
  H. Ito, Y. Sasaki, M. Sawamura, J. Am. Chem. Soc. 130 (2008) 15774–15775 doi: 10.1021/ja806602h
14. [14]
  T.S.N. Zhao, Y. Yang, T. Lessing, K.J. Szabo, J. Am. Chem. Soc. 136 (2014) 7563–7566 doi: 10.1021/ja502792s
15. [15]
  L. Mao, K.J. Szabo, T.B. MarderOrg. Lett. 19 (2017) 1204–1207 doi: 10.1021/acs.orglett.7b00256
16. [16]
  J. Zhao, S.J.T. Jonker, D.N. Meyer, et al., Chem. Sci. 9 (2018) 3305–3312 doi: 10.1039/C7SC05123A
17. [17]
  L. Mao, C. Li, L. Xiang, et al., J. Org. Chem. 85 (2020) 2823–2831 doi: 10.1021/acs.joc.9b03319
18. [18]
  H. Miura, Y. Hachiya, H. Nishio, et al., ACS Catal. 11 (2021) 758–766 doi: 10.1021/acscatal.0c03771
19. [19]
  F.W. Friese, A. Studer, Angew. Chem. Int. Ed. 58 (2019) 9561–9564 doi: 10.1002/anie.201904028
20. [20]
  S.A. Gonsales, Z.C. Mueller, F. Zhao, et al., J. Am. Chem. Soc. 143 (2021) 20640–20644 doi: 10.1021/jacs.1c11453
21. [21]
  T.C. Mancilla, R. Contreras, B. Wrackmeyer, J. Organomet. Chem. 307 (1986) 1–6 doi: 10.1016/0022-328X(86)80169-3
22. [22]
  Z. He, A.K. Yudin, J. Am. Chem. Soc. 133 (2011) 13770–13773 doi: 10.1021/ja205910d
23. [23]
  Z. He, P. Trinchera, S. Adachi, J.D. St Denis, A.K. Yudin, Angew. Chem. Int. Ed. 51 (2012) 11092–11096 doi: 10.1002/anie.201206501
24. [24]
  S. Adachi, S.K. Liew, C.F. Lee, et al., Org. Lett. 17 (2015) 5594–5597 doi: 10.1021/acs.orglett.5b02741
25. [25]
  M.L. Lepage, S. Lai, N. Peressin, et al., Angew. Chem. Int. Ed. 56 (2017) 15257–15261 doi: 10.1002/anie.201707125
26. [26]
  J. Taguchi, T. Ikeda, R. Takahashi, et al., Angew. Chem. Int. Ed. 56 (2017) 13847–13851 doi: 10.1002/anie.201707933
27. [27]
  D.H. Tan, Y.H. Cai, Y.F. Zeng, et al., Angew. Chem. Int. Ed. 58 (2019) 13784–13788 doi: 10.1002/anie.201907349
28. [28]
  Y.M. Ivon, I.V. Mazurenko, Y.O. Kuchkovska, Z.V. Voitenko, O.O. Grygorenko, Angew. Chem. Int. Ed. 59 (2020) 18016–18022 doi: 10.1002/anie.202007651
29. [29]
  Q. Wang, M. Biosca, F. Himo, K.J. Szabo, Angew. Chem. Int. Ed. 60 (2021) 26327–26331 doi: 10.1002/anie.202109461
30. [30]
  W.X. Lv, Y. Li, Y.H. Cai, et al., Chem. Sci. 13 (2022) 2981–2984 doi: 10.1039/d1sc06508d
31. [31]
  L. Yang, D.H. Tan, W.X. Fan, et al., Angew. Chem. Int. Ed. 60 (2021) 3454–3458 doi: 10.1002/anie.202011872
32. [32]
  Y.M. Ivon, Y.O. Kuchkovska, Z.V. Voitenko, O.O. Grygorenko, Eur. J. Org. Chem. 2020 (2020) 3367–3377 doi: 10.1002/ejoc.202000078
33. [33]
  Y.F. Zeng, X.G. Liu, D.H. Tan, et al., Chem. Commun. 56 (2020) 4332–4335 doi: 10.1039/d0cc00722f
34. [34]
  S. Li, M. Li, S.S. Li, J. Wang, Chem. Commun. 58 (2022) 399–402 doi: 10.1039/d1cc06170d
35. [35]
  Q.I. Churches, J.F. Hooper, C.A. Hutton, J. Org. Chem. 80 (2015) 5428–5435 doi: 10.1021/acs.joc.5b00182
36. [36]
  A.M. Kelly, P.J. Chen, J. Klubnick, D.J. Blair, M.D. Burke, Org. Lett. 22 (2020) 9408–9414 doi: 10.1021/acs.orglett.0c02449
37. [37]
  S.J. Lee, T.M. Anderson, M.D. Burke, Angew. Chem. Int. Ed. 49 (2010) 8860–8863 doi: 10.1002/anie.201004911
38. [38]
  J.R. Struble, S.J. Lee, M.D. Burke, Tetrahedron 66 (2010) 4710–4718 doi: 10.1016/j.tet.2010.04.020
39. [39]
  E.M. Woerly, A.H. Cherney, E.K. Davis, M.D. Burke, J. Am. Chem. Soc. 132 (2010) 6941–6943 doi: 10.1021/ja102721p
40. [40]
  J. Li, S.G. Ballmer, E.P. Gillis, et al., Science 347 (2015) 1221–1226 doi: 10.1126/science.aaa5414
41. [41]
  A.G. Myers, B. Zheng, J. Am. Chem. Soc. 118 (1996) 4492–4493 doi: 10.1021/ja960443w
42. [42]
  M. Movassaghi, O.K. Ahmad, J. Org. Chem. 72 (2007) 1838–1841 doi: 10.1021/jo062325p
43. [43]
  X.F. Ren, J.L. Xu, S.H. Chen, Chin. J. Org. Chem. 26 (2006) 454–461
44. [44]
  Z. Liu, P. Liao, X. Bi, Chem. Eur. J. 20 (2014) 17277–17281 doi: 10.1002/chem.201404692
45. [45]
  S. Ma, Acc. Chem. Res. 42 (2009) 1679–1688 doi: 10.1021/ar900153r
46. [46]
  X.L. Han, P.P. Lin, Q. Li, Chin. Chem. Lett. 30 (2019) 1495–1502 doi: 10.1016/j.cclet.2019.04.027
47. [47]
  K. Li, M. Nie, W. Tang, Green Synth. Catal. 1 (2020) 171–174 doi: 10.1016/j.gresc.2020.08.003
48. [48]
  G.Z. Tian, X.L. Wang, J. Hu, et al., Chin. Chem. Lett. 26 (2015) 922–930 doi: 10.1016/j.cclet.2015.04.026
49. [49]
  K. Ishizawa, S. Majima, X.F. Wei, et al., J. Org. Chem. 84 (2019) 10615–10628 doi: 10.1021/acs.joc.9b00887
1. [1]
  Yiming Yang , Lichao Sun , Qingfeng Zhang . Plasmonic nanocrystals with intrinsic chirality: Biomolecule-directed synthesis and applications. Chinese Journal of Structural Chemistry, 2025, 44(1): 100467-100467. doi: 10.1016/j.cjsc.2024.100467
2. [2]
  Sifan Du , Yuan Wang , Fulin Wang , Tianyu Wang , Li Zhang , Minghua Liu . Evolution of hollow nanosphere to microtube in the self-assembly of chiral dansyl derivatives and inversed circularly polarized luminescence. Chinese Chemical Letters, 2024, 35(7): 109256-. doi: 10.1016/j.cclet.2023.109256
3. [3]
  Xue-Zhi Wang , Yi-Tong Liu , Chuang-Wei Zhou , Bei Wang , Dong Luo , Mo Xie , Meng-Ying Sun , Yong-Liang Huang , Jie Luo , Yan Wu , Shuixing Zhang , Xiao-Ping Zhou , Dan Li . Amplified circularly polarized luminescence of chiral metal-organic frameworks via post-synthetic installing pillars. Chinese Chemical Letters, 2024, 35(10): 109380-. doi: 10.1016/j.cclet.2023.109380
4. [4]
  Yiqian Jiang , Zihan Yang , Xiuru Bi , Nan Yao , Peiqing Zhao , Xu Meng . Mediated electron transfer process in α-MnO₂ catalyzed Fenton-like reaction for oxytetracycline degradation. Chinese Chemical Letters, 2024, 35(8): 109331-. doi: 10.1016/j.cclet.2023.109331
5. [5]
  Quanyou Guo , Yue Yang , Tingting Hu , Hongqi Chu , Lijun Liao , Xuepeng Wang , Zhenzi Li , Liping Guo , Wei Zhou . Regulating local electron transfer environment of covalent triazine frameworks through F, N co-modification towards optimized oxygen reduction reaction. Chinese Chemical Letters, 2025, 36(1): 110235-. doi: 10.1016/j.cclet.2024.110235
6. [6]
  Bowen Wang , Longwu Sun , Qianqian Cao , Xinzhi Li , Jianai Chen , Shizhao Wang , Miaolin Ke , Fener Chen . Cu-catalyzed three-component CSP coupling for the synthesis of trisubstituted allenyl phosphorothioates. Chinese Chemical Letters, 2024, 35(12): 109617-. doi: 10.1016/j.cclet.2024.109617
7. [7]
  Liangfeng Yang , Liang Zeng , Yanping Zhu , Qiuan Wang , Jinheng Li . Copper-catalyzed photoredox 1,4-amidocyanation of 1,3-enynes with N-amidopyridin-1-ium salts and TMSCN: Facile access to α-amido allenyl nitriles. Chinese Chemical Letters, 2024, 35(11): 109685-. doi: 10.1016/j.cclet.2024.109685
8. [8]
  Mei Peng , Wei-Min He . Photochemical synthesis and group transfer reactions of azoxy compounds. Chinese Chemical Letters, 2024, 35(8): 109899-. doi: 10.1016/j.cclet.2024.109899
9. [9]
  Ming Huang , Xiuju Cai , Yan Liu , Zhuofeng Ke . Base-controlled NHC-Ru-catalyzed transfer hydrogenation and α-methylation/transfer hydrogenation of ketones using methanol. Chinese Chemical Letters, 2024, 35(7): 109323-. doi: 10.1016/j.cclet.2023.109323
10. [10]
  Minghao Hu , Tianci Xie , Yuqiang Hu , Longjie Li , Ting Wang , Tongbo Wu . Allosteric DNAzyme-based encoder for molecular information transfer. Chinese Chemical Letters, 2024, 35(7): 109232-. doi: 10.1016/j.cclet.2023.109232
11. [11]
  Chenghao Ge , Peng Wang , Pei Yuan , Tai Wu , Rongjun Zhao , Rong Huang , Lin Xie , Yong Hua . Tuning hot carrier transfer dynamics by perovskite surface modification. Chinese Chemical Letters, 2024, 35(10): 109352-. doi: 10.1016/j.cclet.2023.109352
12. [12]
  Er-Meng Wang , Ziyi Wang , Xu Ban , Xiaowei Zhao , Yanli Yin , Zhiyong Jiang . Chemoselective photocatalytic sulfenylamination of alkenes with sulfenamides via energy transfer. Chinese Chemical Letters, 2024, 35(12): 109843-. doi: 10.1016/j.cclet.2024.109843
13. [13]
  Rui Wang , Yang Liang , Julius Rebek Jr. , Yang Yu . Stabilization and detection of labile reaction intermediates in supramolecular containers. Chinese Chemical Letters, 2024, 35(6): 109228-. doi: 10.1016/j.cclet.2023.109228
14. [14]
  Xin Li , Zhen Xu , Donglei Bu , Jinming Cai , Huamei Chen , Qi Chen , Ting Chen , Fang Cheng , Lifeng Chi , Wenjie Dong , Zhenchao Dong , Shixuan Du , Qitang Fan , Xing Fan , Qiang Fu , Song Gao , Jing Guo , Weijun Guo , Yang He , Shimin Hou , Ying Jiang , Huihui Kong , Baojun Li , Dengyuan Li , Jie Li , Qing Li , Ruoning Li , Shuying Li , Yuxuan Lin , Mengxi Liu , Peinian Liu , Yanyan Liu , Jingtao Lü , Chuanxu Ma , Haoyang Pan , JinLiang Pan , Minghu Pan , Xiaohui Qiu , Ziyong Shen , Shijing Tan , Bing Wang , Dong Wang , Li Wang , Lili Wang , Tao Wang , Xiang Wang , Xingyue Wang , Xueyan Wang , Yansong Wang , Yu Wang , Kai Wu , Wei Xu , Na Xue , Linghao Yan , Fan Yang , Zhiyong Yang , Chi Zhang , Xue Zhang , Yang Zhang , Yao Zhang , Xiong Zhou , Junfa Zhu , Yajie Zhang , Feixue Gao , Yongfeng Wang . Recent progress on surface chemistry Ⅰ: Assembly and reaction. Chinese Chemical Letters, 2024, 35(12): 110055-. doi: 10.1016/j.cclet.2024.110055
15. [15]
  Kexin Yuan , Yulei Liu , Haoran Feng , Yi Liu , Jun Cheng , Beiyang Luo , Qinglian Wu , Xinyu Zhang , Ying Wang , Xian Bao , Wanqian Guo , Jun Ma . Unlocking the potential of thin-film composite reverse osmosis membrane performance: Insights from mass transfer modeling. Chinese Chemical Letters, 2024, 35(5): 109022-. doi: 10.1016/j.cclet.2023.109022
16. [16]
  Zhao-Xia Lian , Xue-Zhi Wang , Chuang-Wei Zhou , Jiayu Li , Ming-De Li , Xiao-Ping Zhou , Dan Li . Producing circularly polarized luminescence by radiative energy transfer from achiral metal-organic cage to chiral organic molecules. Chinese Chemical Letters, 2024, 35(8): 109063-. doi: 10.1016/j.cclet.2023.109063
17. [17]
  Chunxiu Yu , Zelin Wu , Hongle Shi , Lingyun Gu , Kexin Chen , Chuan-Shu He , Yang Liu , Heng Zhang , Peng Zhou , Zhaokun Xiong , Bo Lai . Insights into the electron transfer mechanisms of peroxydisulfate activation by modified metal-free acetylene black for degradation of sulfisoxazole. Chinese Chemical Letters, 2024, 35(8): 109334-. doi: 10.1016/j.cclet.2023.109334
18. [18]
  Haoyang Wang , Ronghao Zhang , Yanlun Ren , Li Zhang . A convenient method for measuring gas-liquid volumetric mass transfer coefficient in micro reactors. Chinese Chemical Letters, 2024, 35(4): 108833-. doi: 10.1016/j.cclet.2023.108833
19. [19]
  Chaoqun Ma , Yuebo Wang , Ning Han , Rongzhen Zhang , Hui Liu , Xiaofeng Sun , Lingbao Xing . Carbon dot-based artificial light-harvesting systems with sequential energy transfer and white light emission for photocatalysis. Chinese Chemical Letters, 2024, 35(4): 108632-. doi: 10.1016/j.cclet.2023.108632
20. [20]
  Xiao-Ya Yuan , Cong-Cong Wang , Bing Yu . Recent advances in FeCl₃-photocatalyzed organic reactions via hydrogen-atom transfer. Chinese Chemical Letters, 2024, 35(9): 109517-. doi: 10.1016/j.cclet.2024.109517

Get Citation

PDF

XML

Metrics

PDF Downloads(9)
Abstract views(638)
HTML views(60)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142