Citation: Qian Chang Ding, Yun Feng Du, Xin Sheng Li, Dong Cheng Xu. Convenient synthesis of chiral H₄-BINOL via direct hydrogenation of BINOL[J]. Chinese Chemical Letters, ;2010, 21(11): 1277-1280. doi: 10.1016/j.cclet.2010.07.013 shu

Convenient synthesis of chiral H₄-BINOL via direct hydrogenation of BINOL

Zhejiang Key Laboratory for Reactive Chemistry on Solid Surfaces, Institute of Physical Chemistry, Zhejiang Normal University, Jinhua, 321004, China

Received Date: 19 January 2010

Fund Project: The project was supported by the Science and Technology Department of Zhejiang Province (no.2008C21041) and was partially supported by the NSFC (no.20572101).

A simple, highly effective hydrogenation of chiral BINOL to provide H₄-BINOL in multigram scale with good yield (up to 78% yield) was developed. A series of heterogeneous catalysts was tested in the hydrogenation; the best result was obtained with 5% Pd/C in EtOH under the H₂ pressure of 50 bar for 2 h. This method is a more useful method for practical synthesis of optically pure H₄-BINOL than other available methods.
- Hydrogenation,
- 1,1'-Bi-2-naphthol,
- 5,6,7,8-Tetrahydro-1,1'-bi-2-naphthol,
- Chiral,
- Pd/C
1. [1]
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2. [2]
  Lingyun Shen , Shenxiang Yin , Qingshu Zheng , Zheming Sun , Wei Wang , Tao Tu . A rechargeable and portable hydrogen storage system grounded on soda water. Chinese Chemical Letters, 2025, 36(3): 110580-. doi: 10.1016/j.cclet.2024.110580
3. [3]
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4. [4]
  Ruixue Liu , Xiaobing Ding , Qiwei Lang , Gen-Qiang Chen , Xumu Zhang . Enantioselective and divergent construction of chiral amino alcohols and oxazolidin-2-ones via Ir-f-phamidol-catalyzed dynamic kinetic asymmetric hydrogenation. Chinese Chemical Letters, 2025, 36(3): 110037-. doi: 10.1016/j.cclet.2024.110037
5. [5]
  Hai-Yang Song , Jun Jiang , Yu-Hang Song , Min-Hang Zhou , Chao Wu , Xiang Chen , Wei-Min He . Supporting-electrolyte-free electrochemical [2 + 2 + 1] annulation of benzo[d]isothiazole 1,1-dioxides, N-arylglycines and paraformaldehyde. Chinese Chemical Letters, 2024, 35(6): 109246-. doi: 10.1016/j.cclet.2023.109246
6. [6]
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7. [7]
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8. [8]
  Mengjun Zhao , Yuhao Guo , Na Li , Tingjiang Yan . Deciphering the structural evolution and real active ingredients of iron oxides in photocatalytic CO2 hydrogenation. Chinese Journal of Structural Chemistry, 2024, 43(8): 100348-100348. doi: 10.1016/j.cjsc.2024.100348
9. [9]
  Sanmei Wang , Dengxin Yan , Wenhua Zhang , Liangbing Wang . Graphene-supported isolated platinum atoms and platinum dimers for CO₂ hydrogenation: Catalytic activity and selectivity variations. Chinese Chemical Letters, 2025, 36(4): 110611-. doi: 10.1016/j.cclet.2024.110611
10. [10]
  Huihua GONG , Tianhua CUI , Li JI , Jichuan ZHANG , Liyuan ZHANG , Yan CHEN , Zhenye WANG , Jiaqi XU , Ruixiang LI . Hydrogenation of CO₂ to formate catalyzed by N-heterocyclic carbene-nitrogen-phosphine chelated iridium(Ⅰ) complexes. Chinese Journal of Inorganic Chemistry, 2025, 41(12): 2609-2620. doi: 10.11862/CJIC.20250170
11. [11]
  Guilan He , Yaofeng Yuan . 手性二茂铁双膦配体Xyliphos的合成及应用. University Chemistry, 2025, 40(8): 130-137. doi: 10.12461/PKU.DXHX202409122
12. [12]
  Long Jin , Jian Han , Dongmei Fang , Min Wang , Jian Liao . Pd-catalyzed asymmetric carbonyl alkynylation: Synthesis of axial chiral ynones. Chinese Chemical Letters, 2024, 35(6): 109212-. doi: 10.1016/j.cclet.2023.109212
13. [13]
  Yang Liu , Jing Liang , Mengzhu Zheng , Haoze Song , Lixia Chen , Hua Li . PD-L1/SHP2 dual PROTACs inhibit melanoma by enhancing T-cell killing activity. Chinese Chemical Letters, 2025, 36(6): 110317-. doi: 10.1016/j.cclet.2024.110317
14. [14]
  Zixuan Zhu , Xianjin Shi , Yongfang Rao , Yu Huang . Recent progress of MgO-based materials in CO₂ adsorption and conversion: Modification methods, reaction condition, and CO₂ hydrogenation. Chinese Chemical Letters, 2024, 35(5): 108954-. doi: 10.1016/j.cclet.2023.108954
15. [15]
  An Lu , Yuhao Guo , Yi Yan , Lin Zhai , Xiangyu Wang , Weiran Cao , Zijie Li , Zhixia Zhao , Yujie Shi , Yuanjun Zhu , Xiaoyan Liu , Huining He , Zhiyu Wang , Jian-Cheng Wang . Nanomedicine integrating the lipidic derivative of 5-fluorouracil, miriplatin and PD-L1 siRNA for enhancing tumor therapy. Chinese Chemical Letters, 2024, 35(6): 108928-. doi: 10.1016/j.cclet.2023.108928
16. [16]
  Jiang Gong , Fengling Zheng , Hanqing Zhang , Weihan Shu , Hao Wang , Ni Zhang , Pengbing Huang , Chuancai Zhang , Bin Dai . The interfacial effect of SiO₂-Ni₃Mo₃N efficiently catalyzes the low-temperature hydrogenation of dimethyl oxalate to ethanol. Chinese Chemical Letters, 2025, 36(8): 111122-. doi: 10.1016/j.cclet.2025.111122
17. [17]
  Hailian Tang , Siyuan Chen , Qiaoyun Liu , Guoyi Bai , Botao Qiao , Liu Fei . Stabilized Rh/hydroxyapatite Catalyst for Furfuryl Alcohol Hydrogenation: Application of Oxidative Strong Metal-Support Interactions in Reducing Conditions. Acta Physico-Chimica Sinica, 2025, 41(4): 100036-0. doi: 10.3866/PKU.WHXB202408004
18. [18]
  Qin Cheng , Ming Huang , Qingqing Ye , Bangwei Deng , Fan Dong . Indium-based electrocatalysts for CO₂ reduction to C1 products. Chinese Chemical Letters, 2024, 35(6): 109112-. doi: 10.1016/j.cclet.2023.109112
19. [19]
  Xin Li , Jia-Min Lu , Bo Li , Chen Zhao , Bei-Bei Yang , Li Li . Chiroptical sensing for remote chiral amines via a C–H activation reaction. Chinese Chemical Letters, 2025, 36(5): 110310-. doi: 10.1016/j.cclet.2024.110310
20. [20]
  Mao-Fan Li , Ming‐Yu Guo , De-Xuan Liu , Xiao-Xian Chen , Wei-Jian Xu , Wei-Xiong Zhang . Multi-stimuli responsive behaviors in a new chiral hybrid nitroprusside salt (R-3-hydroxypyrrolidinium)₂[Fe(CN)₅(NO)]. Chinese Chemical Letters, 2024, 35(12): 109507-. doi: 10.1016/j.cclet.2024.109507