Citation: Ma Xiantao, Yu Jing, Ma Ruitian, Yan Ran, Zhang Zhenlei. Palladium-Catalyzed Dehydrative Cross Couplings of Stabilized Phosphorus Ylides with Allylic Alcohols[J]. Chinese Journal of Organic Chemistry, ;2019, 39(3): 830-835. doi: 10.6023/cjoc201812051 shu

Palladium-Catalyzed Dehydrative Cross Couplings of Stabilized Phosphorus Ylides with Allylic Alcohols

Ma Xiantao ^a,, ,
Yu Jing ^a ,
Ma Ruitian ^a ,
Yan Ran ^a ,
Zhang Zhenlei ^a,b,,

a.
College of Chemistry and Chemical Engineering, Xinyang Normal University, Xinyang 464000
b.
School of Chemistry and Material Engineering, Fuyang Normal University, Fuyang 236037

Corresponding author: Ma Xiantao, xiantaoma@126.com Zhang Zhenlei, helenken@mail.ustc.edu.cn
Received Date: 31 December 2018
Revised Date: 27 January 2019
Available Online: 22 March 2019
Fund Project: Project supported by the Scientific Research Project of Henan Province (No. 19B150018), the Nanhu Scholars Program for Young Scholars of Xinyang Normal University and the Young Core Instructor Program of Xinyang Normal University (No. 2018GGJS-05)the Nanhu Scholars Program for Young Scholars of Xinyang Normal University and the Young Core Instructor Program of Xinyang Normal University 2018GGJS-05the Scientific Research Project of Henan Province 19B150018

Figures(2)

A dehydrative cross coupling of ketone-stabilized phosphorus ylides with the readily available allylic alcohols followed by an one-pot Wittig reaction is developed. A range of functional 1, 4-dienes could be obtained in 52%~95% isolated yields in the presence of 5 mol% Pd(PPh₃) ₄ and 20 mol% B(OH) ₃. The same method can be extended to ester or nitrile-stabi-lized phosphorus ylides, affording the corresponding 1, 4-dienes in moderate yields.
- stabilized phosphorus ylides,
- allylic alcohols,
- dehydrative cross couplings,
- palladium catalysis
1. [1]
  (a) Jie, M. S. F. L. K.; Pasha, M. K.; Syed-Rahmatulla, M. S. K. Nat. Prod. Rep. 1997, 14, 163.
  (b) Fürstner, A.; Nevado, C.; Waser, M.; Tremblay, M.; Chevrier, C.; Teplý, F.; Aï ssa, C.; Moulin, E.; Müller, O. J. Am. Chem. Soc. 2007, 129, 9150.
  (c) Wilson, M. C.; Nam, S.-J.; Gulder, T. A. M.; Kauffman, C. A.; Jensen, P. R.; Fenical, W.; Moore, B. S. J. Am. Chem. Soc. 2011, 133, 1971.
2. [2]
  (a) Macklin, T. K.; Micalizio, G. C. Nat. Chem. 2010, 2, 638.
  (b) Sharma, R. K.; RajanBabu, T. V. J. Am. Chem. Soc. 2010, 132, 3295.
  (c) Trost, B. M.; Luan, X. J. Am. Chem. Soc. 2011, 133, 1706.
  (d) McCammant, M. S.; Liao, L.; Sigman, M. S. J. Am. Chem. Soc. 2013, 135, 4167.
  (e) Jin, W.; Yang, Q.; Wu, P.; Chen, J.; Yu, Z. Adv. Synth. Catal. 2014, 360, 2097.
3. [3]
  (a) Miyaura, N.; Yano, T.; Suzuki, A. Tetrahedron Lett. 1980, 21, 2865.
  (b) Kabalka, G. W.; Al-Masum, M. Org. Lett. 2006, 8, 11.
  (c) Lee, Y.; Akiyama, K.; Gillingham, D. G.; Brown, M. K.; Hoveyda, A. H. J. Am. Chem. Soc. 2008, 130, 446.
  (d) Akiyama, K.; Gao, F.; Hoveyda, A. H. Angew. Chem., Int. Ed. 2010, 49, 419.
  (e) Gao, F.; Lee, K. P.; McGrath, Y.; Hoveyda, A. H. J. Am. Chem. Soc. 2010, 132, 14315.
  (f) Gao, F.; Carr, J. L.; Hoveyda, A. H. Angew. Chem., Int. Ed. 2012, 51, 6613.
  (g) Huang, Y.; Fañ anás-Mastral, M.; Minnaard, A. J.; Feringa, B. L. Chem. Commun. 2013, 49, 3309.
  (h) Hamilton, J. Y.; Sarlah, D.; Carreira, E. M. J. Am. Chem. Soc. 2013, 135, 994.
  (i) Gao, F.; Carr, J. L.; Hoveyda, A. H. J. Am. Chem. Soc. 2014, 136, 2149.
  (j) Sidera, M.; Fletcher, S. P. Chem. Commun. 2015, 51, 5044.
  (k) Zhurkin, F. E.; Hu, X. J. Org. Chem. 2016, 81, 5795.
  (l) Yang, B.; Wang, Z.-X. J. Org. Chem. 2017, 82, 4542.
4. [4]
  (a) Cornella, J.; Zarate, C.; Martin, R. Chem. Soc. Rev. 2014, 43, 8081.
  (b) Matsubara, R.; Jamison, T. F. J. Am. Chem. Soc. 2010, 132, 6880.
  (c) Matsubara, R.; Jamison, T. F. Chem. Asian J. 2011, 6, 1860.
  (d) Ye, K.-Y.; He, H.; Liu, W.-B.; Dai, L.-X.; Helmchen, G.; You, S.-L. J. Am. Chem. Soc. 2011, 133, 19006.
  (e) Hamilton, J. Y.; Sarlah, D.; Carreira, E. M. J. Am. Chem. Soc. 2014, 13 6, 2006.
  (f) Gumrukcu, Y.; de Bruin, B.; Reek, J. N. H. Chem.-Eur. J. 2014, 20, 10905.
5. [5]
  (a) Thadani, A. N.; Rawal, V. H. Org. Lett. 2002, 4, 4317.
  (b) Chen, X.; Chen, D.; Lu, Z.; Kong, L.; Zhu, G.-G. J. Org. Chem. 2011, 76, 6338.
  (c) Wen, Y.; Jiang, H.-F. Tetrahedron Lett. 2013, 54, 4034.
  (d) Todd, D. P.; Thompson, B. B.; Nett, A. J.; Montgomery, J. J. Am. Chem. Soc. 2015, 137, 12788
  (e) Mateos, J.; Rivera-Chao, E.; Fañ anás-Mastral, M. ACS Catal. 2017, 7, 5340.
6. [6]
  For rare examples for terminal skipped dienes synthesis, see: (a) Basavaiah, D.; Kumaragurubaran, N.; Sharada, D. S. Tetrahedron Lett. 2001, 42, 85.
  (b) Basavaiah, D.; Sharada, D. S.; Kumaragurubaran, N.; Reddy, R. M. J. Org. Chem. 2002, 67, 7135.
  (c) Li, Y.-Q.; Wang, H.-J.; Huang, Z.-Z. J. Org. Chem. 2016, 81, 4429.
7. [7]
8. [8]
  (a) Liu, W.-B.; He, H.; Dai, L.-X.; You, S.-L. Chem.-Eur. J. 2010, 16, 7376.
  (b) Ma, X.-T.; Wang, Y.; Dai, R.-H.; Liu, C.-R.; Tian, S.-K. J. Org. Chem. 2013, 78, 11071.
9. [9]
  For reviews, see: (a) Bandini, M. Angew. Chem., Int. Ed. 2011, 50, 994.
  (b) Sundararaju, B.; Achard, M.; Bruneau, C. Chem. Soc. Rev. 2012, 41, 4467.
  (c) Butta, N. A.; Zhang, W. Chem. Soc. Rev. 2015, 44, 7929.
  (d) Ferraccioli, R.; Pignataro, L. Curr. Org. Chem. 2015, 19, 106. For selected recent examples:
  (e) Shen, D.; Chen, Q.; Yan, P.; Zeng, X.; Zhong, G. Angew. Chem., Int. Ed. 2017, 129, 3290.
  (f) Wu, F.-P.; Peng, J.-B.; Fu, L.-Y.; Qi, X.; Wu, X.-F. Org. Lett 2017, 19, 5474.
  (g) Su, Y.-L.; Han, Z.-Y.; Li, Y.-H.; Gong, L.-Z. ACS Catal. 2017, 7, 7917.
  (h) Jia, X.-G.; Guo, P.; Duan, J.; Shu, X.-Z. Chem. Sci. 2018, 9, 640.
10. [10]
  Ma, X.; Yu, J.; Han, C.; Zhou, Q.; Ren, M.; Li, L.; Tang, L. Adv. Synth. Catal. 2019, https://doi.org/10.1002/adsc.201801266.
11. [11]
  (a) Ma, X.-T.; Dai, R.-H.; Zhang, J.; Gu, Y.; Tian, S.-K. Adv. Synth. Catal. 2014, 356, 2984.
  (b) Ma, X.; Yu, L.; Su, C.; Yang, Y.; Li, H.; Xu, Q. Adv. Synth. Catal. 2017, 359, 1649.
  (c) Ma, X.; Xu, Q.; Li, H.; Su, C.; Yu, L.; Zhang, X.; Cao, H.; Han, L.-B. Green Chem. 2018, 20, 3408.
  (d) Ma, X.; Su, C.; Xu, Q. Top. Curr. Chem. 2016, 374, 27.
12. [12]
  Kaszynski, P.; Friedli, A. C.; Michl, J. J. Am. Chem. Soc. 1992, 114, 601. doi: 10.1021/ja00028a029
13. [13]
  Liu, H.-J.; Wynn, H. Tetrahedron Lett. 1982, 23, 3151. doi: 10.1016/S0040-4039(00)88582-2
1. [1]
  Tingbo Wang , Yao Luo , Bingyan Hu , Ruiyuan Liu , Jing Miao , Huizhe Lu . Quantitative Computational Study on the Claisen Rearrangement Reaction of Allyl Phenyl Ethers: An Introduction to a Computational Chemistry Experiment. University Chemistry, 2024, 39(11): 278-285. doi: 10.12461/PKU.DXHX202403082
2. [2]
  Haoyu Sun , Dun Li , Yuanyuan Min , Yingying Wang , Yanyun Ma , Yiqun Zheng , Hongwen Huang . Hierarchical Palladium-Copper-Silver Porous Nanoflowers as Efficient Electrocatalysts for CO₂ Reduction to C₂₊ Products. Acta Physico-Chimica Sinica, 2024, 40(6): 2307007-0. doi: 10.3866/PKU.WHXB202307007
3. [3]
  Renxiao Liang , Zhe Zhong , Zhangling Jin , Lijuan Shi , Yixia Jia . A Palladium/Chiral Phosphoric Acid Relay Catalysis for the One-Pot Three-Step Synthesis of Chiral Tetrahydroquinoline. University Chemistry, 2024, 39(5): 209-217. doi: 10.3866/PKU.DXHX202311024
4. [4]
  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): 2408004-0. doi: 10.3866/PKU.WHXB202408004
5. [5]
  Lili Jiang , Shaoyu Zheng , Xuejiao Liu , Xiaomin Xie . Copper-Catalyzed Oxidative Coupling Reactions for the Synthesis of Aryl Sulfones: A Fundamental and Exploratory Experiment for Undergraduate Teaching. University Chemistry, 2025, 40(7): 267-276. doi: 10.12461/PKU.DXHX202408004
6. [6]
  Yi Yang , Xin Zhou , Miaoli Gu , Bei Cheng , Zhen Wu , Jianjun Zhang . Femtosecond transient absorption spectroscopy investigation on ultrafast electron transfer in S-scheme ZnO/CdIn₂S₄ photocatalyst for H₂O₂ production and benzylamine oxidation. Acta Physico-Chimica Sinica, 2025, 41(6): 100064-0. doi: 10.1016/j.actphy.2025.100064
7. [7]
  Aili Feng , Xin Lu , Peng Liu , Dongju Zhang . Computational Chemistry Study of Acid-Catalyzed Esterification Reactions between Carboxylic Acids and Alcohols. University Chemistry, 2025, 40(3): 92-99. doi: 10.12461/PKU.DXHX202405072
8. [8]
  Zhanggui DUAN , Yi PEI , Shanshan ZHENG , Zhaoyang WANG , Yongguang WANG , Junjie WANG , Yang HU , Chunxin LÜ , Wei ZHONG . Preparation of UiO-66-NH₂ supported copper catalyst and its catalytic activity on alcohol oxidation. Chinese Journal of Inorganic Chemistry, 2024, 40(3): 496-506. doi: 10.11862/CJIC.20230317
9. [9]
  Zhuoming Liang , Ming Chen , Zhiwen Zheng , Kai Chen . Multidimensional Studies on Ketone-Enol Tautomerism of 1,3-Diketones By ¹H NMR. University Chemistry, 2024, 39(7): 361-367. doi: 10.3866/PKU.DXHX202311029
10. [10]
  Yajin Li , Huimin Liu , Lan Ma , Jiaxiong Liu , Dehua He . Photothermal Synthesis of Glycerol Carbonate via Glycerol Carbonylation with CO₂ over Au/Co₃O₄-ZnO Catalyst. Acta Physico-Chimica Sinica, 2024, 40(9): 2308005-0. doi: 10.3866/PKU.WHXB202308005
11. [11]
  Zhuo WANG , Junshan ZHANG , Shaoyan YANG , Lingyan ZHOU , Yedi LI , Yuanpei LAN . Preparation and photocatalytic performance of CeO₂-reduced graphene oxide by thermal decomposition. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1708-1718. doi: 10.11862/CJIC.20240067
12. [12]
  Yiping HUANG , Liqin TANG , Yufan JI , Cheng CHEN , Shuangtao LI , Jingjing HUANG , Xuechao GAO , Xuehong GU . Hollow fiber NaA zeolite membrane for deep dehydration of ethanol solvent by vapor permeation. Chinese Journal of Inorganic Chemistry, 2025, 41(2): 225-234. doi: 10.11862/CJIC.20240224
13. [13]
  Yifeng TAN , Ping CAO , Kai MA , Jingtong LI , Yuheng WANG . Synthesis of pentaerythritol tetra(2-ethylthylhexoate) catalyzed by h-MoO₃/SiO₂. Chinese Journal of Inorganic Chemistry, 2024, 40(11): 2155-2162. doi: 10.11862/CJIC.20240147
14. [14]
  Yuanyuan Ping , Wangqing Kong . 光催化碳氢键官能团化合成1-苯基-1,2-乙二醇. University Chemistry, 2025, 40(6): 238-247. doi: 10.12461/PKU.DXHX202408092
15. [15]
  Mengyang LI , Hao XU , Zhonghao NIU , Chunhua GONG , Weihui ZHONG , Jingli XIE . Highly effective catalytic synthesis of β-amino alcohols by using viologen-polyoxometalate hybrid materials. Chinese Journal of Inorganic Chemistry, 2025, 41(7): 1294-1300. doi: 10.11862/CJIC.20250080
16. [16]
  Yinjie Xu , Suiqin Li , Lihao Liu , Jiahui He , Kai Li , Mengxin Wang , Shuying Zhao , Chun Li , Zhengbin Zhang , Xing Zhong , Jianguo Wang . Enhanced Electrocatalytic Oxidation of Sterols using the Synergistic Effect of NiFe-MOF and Aminoxyl Radicals. Acta Physico-Chimica Sinica, 2024, 40(3): 2305012-0. doi: 10.3866/PKU.WHXB202305012
17. [17]
  Jia Wang , Qing Qin , Zhe Wang , Xuhao Zhao , Yunfei Chen , Liqiang Hou , Shangguo Liu , Xien Liu . P-Doped Carbon-Supported Zn_xP_yO_z for Efficient Ammonia Electrosynthesis under Ambient Conditions. Acta Physico-Chimica Sinica, 2024, 40(3): 2304044-0. doi: 10.3866/PKU.WHXB202304044
18. [18]
  Yawen Guo , Dawei Li , Yang Gao , Cuihong Li . Recent Progress on Stability of Organic Solar Cells Based on Non-Fullerene Acceptors. Acta Physico-Chimica Sinica, 2024, 40(6): 2306050-0. doi: 10.3866/PKU.WHXB202306050
19. [19]
  Bo YANG , Gongxuan LÜ , Jiantai MA . Nickel phosphide modified phosphorus doped gallium oxide for visible light photocatalytic water splitting to hydrogen. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 736-750. doi: 10.11862/CJIC.20230346
20. [20]
  Weihan Zhang , Menglu Wang , Ankang Jia , Wei Deng , Shuxing Bai . Surface Sulfur Species Influence Hydrogenation Performance of Palladium-Sulfur Nanosheets. Acta Physico-Chimica Sinica, 2024, 40(11): 2309043-0. doi: 10.3866/PKU.WHXB202309043

Get Citation

PDF

XML

Metrics

PDF Downloads(8)
Abstract views(2110)
HTML views(309)

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