Citation: Zheng Xue-Li, Zheng Cong-Ye, Zhou Fan-Ding, Fu Hai-Yan, Yuan Mao-Lin, Li Rui-Xiang, Xu Bin, Chen Hua. Highly active rhodium/phosphorus catalytic system for the hydroformylation of α-methylstyrene[J]. Chinese Chemical Letters, ;2016, 27(5): 678-680. doi: 10.1016/j.cclet.2016.01.028 shu

Highly active rhodium/phosphorus catalytic system for the hydroformylation of α-methylstyrene

a.
Key Laboratory of Green Chemistry and Technology of Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064, China
b.
Key Laboratory of Green Chemistry of Sichuan Institutes of Higher Education, Zigong 643000, China

Corresponding author: Zheng Xue-Li, zhengxueli@scu.edu.cn Chen Hua, scuhchen@scu.edu.cn
Received Date: 13 October 2015
Revised Date: 22 December 2015
Accepted Date: 4 January 2016
Available Online: 25 May 2016

Figures(1)

Rhodium catalyzed hydroformylation of α-methylstyrene was investigated in the presence of monodentate phosphine ligands L1-L6. We found that the phosphine with good π-acceptability could efficiently improve the activity of the α-methylstyrene hydroformylation. The big steric hindrance of α-C in α-methylstyrene enhanced the regioselectivity towards the linear aldehyde, which resulted in 3-phenylbutanal as the predominant product (>99.0%). When tris(N-pyrrolyl)phosphine (L1) modified Rh(acac)(CO)₂ was employed as the catalyst, the TOF could reach up to 5786 h^-1 in the α-methylstyrene hydroformylation at relatively mild conditions (110℃, 6 MPa).
- α-Methylstyrene,
- Hydroformylation,
- Rh complex,
- Phosphine,
- Pyrrole
1. [1]
  Koeken A.C.J., Smeets N.M.B.. A bulky phosphite modified rhodium catalyst for efficient hydroformylation of disubstituted alkenes and macromonomers in supercritical carbon dioxide[J]. Catal. Sci. Tech., 2013,3:1036-1045.
2. [2]
  Kwok T.J., Wink D.J.. Characterization and application of catalytic regioselective hydroformylation with a cationic bis(dioxaphospholane)rhodium catalyst precursor[J]. Organometallics, 1993,12:1954-1959.
3. [3]
  Jackstell R., Klein H., Beller M., Wiese K.D., Röttger D.. Synthesis of pyrrolyl-, indolyl-, and carbazolylphosphanes and their catalytic application as ligands in the hydroformylation of 2-pentene[J]. Eur. J. Org. Chem, 2001:3871-3877.
4. [4]
  Zheng C.Y., Mo M., Liang H.R.. Rhodium/bisphosphite catalytic system for hydroformylation of styrene and its derivatives[J]. Appl. Organomet. Chem., 2013,27:474-478.
5. [5]
  Suomalainen P., Reinius H.K., Riihimaki H.. Hydroformylation of 1-hexene and propene with in situ formed rhodium phosphine catalysts[J]. J. Mol. Catal. A Chem., 2001,169:67-78.
6. [6]
  Gulyas H., Szollosy A., Szabo P., Halmos P., Bakos J.. Preparation of new sulfonated triarylphosphanes:control of the selectivity by structural assistance[J]. Eur. J. Org. Chem, 2003:2775-2781.
7. [7]
  Yan Y.G., Zhang X.W., Zhang X.M.. A tetraphosphorus ligand for highly regioselective isomerization-hydroformylation of internal olefins[J]. J. Am. Chem. Soc., 2006,128:16058-16061.
8. [8]
  Boymans E., Janssen M., Muller C., Lutz M., Vogt D.. Rh-catalyzed linear hydroformylation of styrene[J]. Dalton Trans., 2012,42:137-142.
1. [1]
  Yu Mao , Yilin Liu , Xiaochen Wang , Shengyang Ni , Yi Pan , Yi Wang . Acylfluorination of enynes via phosphine and silver catalysis. Chinese Chemical Letters, 2024, 35(8): 109443-. doi: 10.1016/j.cclet.2023.109443
2. [2]
  Zhuwen Wei , Jiayan Chen , Congzhen Xie , Yang Chen , Shifa Zhu . Divergent de novo construction of α-functionalized pyrrole derivatives via coarctate reaction. Chinese Chemical Letters, 2024, 35(12): 109677-. doi: 10.1016/j.cclet.2024.109677
3. [3]
  Chao Chen , Wenwen Yu , Guangen Huang , Xuelian Ren , Xiangli Chen , Yixin Li , Shenggui Liang , Mengmeng Xu , Mingyue Zheng , Yaxi Yang , He Huang , Wei Tang , Bing Zhou . Asymmetric macrocyclization enabled by Rh(Ⅲ)-catalyzed CH activation: Enantioenriched macrocyclic inhibitor of Zika virus infection. Chinese Chemical Letters, 2024, 35(11): 109574-. doi: 10.1016/j.cclet.2024.109574
4. [4]
  Chao Ma , Cong Lin , Jian Li . MicroED as a powerful technique for the structure determination of complex porous materials. Chinese Journal of Structural Chemistry, 2024, 43(3): 100209-100209. doi: 10.1016/j.cjsc.2023.100209
5. [5]
  Mengjuan Sun , Muye Zhou , Yifang Xiao , Hailei Tang , Jinhua Chen , Ruitao Zhang , Chunjiayu Li , Qi Ya , Qian Chen , Jiasheng Tu , Qiyue Wang , Chunmeng Sun . Reversibly size-switchable polyion complex micelles for antiangiogenic cancer therapy. Chinese Chemical Letters, 2024, 35(7): 109110-. doi: 10.1016/j.cclet.2023.109110
6. [6]
  Yuanjin Chen , Xianghui Shi , Dajiang Huang , Junnian Wei , Zhenfeng Xi . Synthesis and reactivity of cobalt dinitrogen complex supported by nonsymmetrical pincer ligand. Chinese Chemical Letters, 2024, 35(7): 109292-. doi: 10.1016/j.cclet.2023.109292
7. [7]
  Peng Meng , Qian-Cheng Luo , Aidan Brock , Xiaodong Wang , Mahboobeh Shahbazi , Aaron Micallef , John McMurtrie , Dongchen Qi , Yan-Zhen Zheng , Jingsan Xu . Molar ratio induced crystal transformation from coordination complex to coordination polymers. Chinese Chemical Letters, 2024, 35(4): 108542-. doi: 10.1016/j.cclet.2023.108542
8. [8]
  Jingwen Zhao , Jianpu Tang , Zhen Cui , Limin Liu , Dayong Yang , Chi Yao . A DNA micro-complex containing polyaptamer for exosome separation and wound healing. Chinese Chemical Letters, 2024, 35(9): 109303-. doi: 10.1016/j.cclet.2023.109303
9. [9]
  Ya-Ping Liu , Zhi-Rong Gui , Zhen-Wen Zhang , Sai-Kang Wang , Wei Lang , Yanzhu Liu , Qian-Yong Cao . A phenylphenthiazide anchored Tb(Ⅲ)-cyclen complex for fluorescent turn-on sensing of ClO⁻. Chinese Chemical Letters, 2025, 36(2): 109769-. doi: 10.1016/j.cclet.2024.109769
10. [10]
  Shulei Hu , Yu Zhang , Xiong Xie , Luhan Li , Kaixian Chen , Hong Liu , Jiang Wang . Rh(Ⅲ)-catalyzed late-stage C-H alkenylation and macrolactamization for the synthesis of cyclic peptides with unique Trp(C7)-alkene crosslinks. Chinese Chemical Letters, 2024, 35(8): 109408-. doi: 10.1016/j.cclet.2023.109408
11. [11]
  Ying Zhao , Yin-Hang Chai , Tian Chen , Jie Zheng , Ting-Ting Li , Francisco Aznarez , Li-Long Dang , Lu-Fang Ma . Size-controlled synthesis and near-infrared photothermal response of Cp* Rh-based metalla[2]catenanes and rectangular metallamacrocycles. Chinese Chemical Letters, 2024, 35(6): 109298-. doi: 10.1016/j.cclet.2023.109298
12. [12]
  Xinghui Yao , Zhouyu Wang , Da-Gang Yu . Sustainable electrosynthesis: Enantioselective electrochemical Rh(III)/chiral carboxylic acid-catalyzed oxidative CH cyclization coupled with hydrogen evolution reaction. Chinese Chemical Letters, 2024, 35(9): 109916-. doi: 10.1016/j.cclet.2024.109916
13. [13]
  Jianing He , Xiao Wang , Zijian Wang , Ruize Jiang , Ke Wang , Rui Zhang , Huilin Wang , Baokang Geng , Hongyi Gao , Shuyan Song , Hongjie Zhang . Investigation on Cu promotion effect on Ce-based solid solution-anchored Rh single atoms for three-way catalysis. Chinese Chemical Letters, 2025, 36(2): 109640-. doi: 10.1016/j.cclet.2024.109640
14. [14]
  Yingying Yan , Wanhe Jia , Rui Cai , Chun Liu . An AIPE-active fluorinated cationic Pt(Ⅱ) complex for efficient detection of picric acid in aqueous media. Chinese Chemical Letters, 2024, 35(5): 108819-. doi: 10.1016/j.cclet.2023.108819
15. [15]
  Jian Peng , Yue Jiang , Shuangyu Wu , Yanran Cheng , Jingyu Liang , Yixin Wang , Zhuo Li , Sijie Lin . A nonradical oxidation process initiated by Ti-peroxo complex showed high specificity toward the degradation of tetracycline antibiotics. Chinese Chemical Letters, 2024, 35(5): 108903-. doi: 10.1016/j.cclet.2023.108903
16. [16]
  Wenjuan Jin , Zelong Chen , Yi Wang , Jiaxuan Li , Jiahui Li , Yuxin Pei , Zhichao Pei . Nano metal-photosensitizer based on Aza-BODIPY-Cu complex for CDT-enhanced dual phototherapy. Chinese Chemical Letters, 2024, 35(7): 109328-. doi: 10.1016/j.cclet.2023.109328
17. [17]
  Jinyu Guo , Yandai Lin , Shaohua He , Yueqing Chen , Fenglu Li , Renjie Ruan , Gaoxing Pan , Hexin Nan , Jibin Song , Jin Zhang . Utilizing dual-responsive iridium(Ⅲ) complex for hepatocellular carcinoma: Integrating photoacoustic imaging with chemotherapy and photodynamic therapy. Chinese Chemical Letters, 2024, 35(9): 109537-. doi: 10.1016/j.cclet.2024.109537
18. [18]
  Zhengyi Shi , Jie Yin , Yang Xiao , Zhangrong Hou , Fei Song , Jianping Wang , Qingyi Tong , Changxing Qi , Yonghui Zhang . Unprecedented sesquiterpene-polycyclic polyprenylated acylphloroglucinol adduct against acute myeloid leukemia via inhibiting mitochondrial complex Ⅴ. Chinese Chemical Letters, 2024, 35(10): 109458-. doi: 10.1016/j.cclet.2023.109458
19. [19]
  Rong-Nan Yi , Wei-Min He . Electron donor-acceptor complex enabled arylation of dithiocarbamate anions with thianthrenium salts under aqueous micellar conditions. Chinese Chemical Letters, 2024, 35(11): 110194-. doi: 10.1016/j.cclet.2024.110194
20. [20]
  Bing Shen , Tongwei Yuan , Wenshuang Zhang , Yang Chen , Jiaqiang Xu . Complex shell Fe-ZnO derived from ZIF-8 as high-quality acetone MEMS sensor. Chinese Chemical Letters, 2024, 35(11): 109490-. doi: 10.1016/j.cclet.2024.109490

Get Citation

PDF

XML

Metrics

PDF Downloads(2)
Abstract views(629)
HTML views(36)

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