Citation: Wen Yan Hao, Jian Wen Jiang, Ming Zhong Cai. A facile stereospecific synthesis of (Z)-2-sulfonyl-substituted 1, 3-enynes via Sonogashira coupling of (E)-α-iodovinyl sulfones with 1-alkynes[J]. Chinese Chemical Letters, ;2007, 18(7): 773-776. doi: 10.1016/j.cclet.2007.05.021 shu

A facile stereospecific synthesis of (Z)-2-sulfonyl-substituted 1, 3-enynes via Sonogashira coupling of (E)-α-iodovinyl sulfones with 1-alkynes

Department of Chemistry, Jiangxi Normal University, Nanchang 330022, China

Received Date: 1 March 2007

Fund Project: We thank the National Natural Science Foundation of China (No. 20462002) and Natural Science Foundation of Jiangxi Province (No. 0420015) for financial support.

(E)-α-Iodovinyl sulfones 1 underwent the Sonogashira coupling reactions with terminal alkynes 2 in piperidine at room temperature in the presence of 5 mol% of Pd(PPh₃)₄ and 10 mol% of CuI to stereospecifically afford the corresponding (Z)-2-sulfonyl-substituted 1, 3-enynes 3 in high yields.
- (E)-α-Iodovinyl sulfone,
- 1, 3-Enynylsulfone,
- Sonogashira coupling,
- Terminal alkyne
1. [1]
  Yajun Hou , Jinxin Liu , Tao Chen , Yi Zhang , Lei Zhou . Sonogashira coupling reaction in ionic liquids: a detailed exploration of experiment 4.4D in the “101 Plan” synthetic chemistry curriculum. University Chemistry, 2026, 41(6): 136-144. doi: 10.12461/PKU.DXHX202510101
2. [2]
  Jinge Zhu , Ailing Tang , Leyi Tang , Peiqing Cong , Chao Li , Qing Guo , Zongtao Wang , Xiaoru Xu , Jiang Wu , Erjun Zhou . Chlorination of benzyl group on the terminal unit of A₂-A₁-D-A₁-A₂ type nonfullerene acceptor for high-voltage organic solar cells. Chinese Chemical Letters, 2025, 36(1): 110233-. doi: 10.1016/j.cclet.2024.110233
3. [3]
  Fangxiang SUN , Qing ZHANG , Yifan ZHANG , Haoyi SUN , Akim V. Shmal′ko , Sergey A. Anufriev , Igor B. Sivaev , Deshuang TU , Hong YAN . Pd-catalyzed B—H bond activation and annulation of nido-carborane with terminal olefins: Facile construction of 2D-3D fused polycyclic compounds. Chinese Journal of Inorganic Chemistry, 2026, 42(3): 467-478. doi: 10.11862/CJIC.20250347
4. [4]
  Rong-Nan Yi , Jun Jiang , Wei-Min He . Pd/NHC-catalyzed ring-opening cross-coupling of gem-difluorocyclopropanes via a 3,3′-reductive elimination pathway. Chinese Chemical Letters, 2026, 37(4): 112163-. doi: 10.1016/j.cclet.2025.112163
5. [5]
  Youxiang He , Yongfa Zhu , Ming Luo , Haiping Xia . A nonalternant analogue of pentacene incorporating a non-terminal azulene unit. Chinese Chemical Letters, 2025, 36(7): 110463-. doi: 10.1016/j.cclet.2024.110463
6. [6]
  Yuemin Chen , Yunqi Wu , Guoao Wang , Feihu Cui , Haitao Tang , Yingming Pan . Electricity-driven enantioselective cross-dehydrogenative coupling of two C(sp³)-H bonds enabled by organocatalysis. Chinese Chemical Letters, 2024, 35(9): 109445-. doi: 10.1016/j.cclet.2023.109445
7. [7]
  Yuexiang Liu , Xiangqiao Yang , Tong Lin , Guantian Yang , Xiaoyong Xu , Bubing Zeng , Zhong Li , Weiping Zhu , Xuhong Qian . Efficient continuous synthesis of 2-[3-(trifluoromethyl)phenyl]malonic acid, a key intermediate of Triflumezopyrim, coupling with esterification-condensation-hydrolysis. Chinese Chemical Letters, 2025, 36(1): 109747-. doi: 10.1016/j.cclet.2024.109747
8. [8]
  Jingfeng Lan , Li Wu , Guangnong Lu , Liu Yang , Xiaolong Li , Xiangyang Xu , Yongwen Shen , E Yu . Application of 3E Method in the Negative List Management System in Teaching Laboratory. University Chemistry, 2024, 39(4): 54-61. doi: 10.3866/PKU.DXHX202310130
9. [9]
  Jian-Rong Li , Jieying Hu , Lai-Hon Chung , Jilong Zhou , Parijat Borah , Zhiqing Lin , Yuan-Hui Zhong , Hua-Qun Zhou , Xianghua Yang , Zhengtao Xu , Jun He . Insight into stable, concentrated radicals from sulfur-functionalized alkyne-rich crystalline frameworks and application in solar-to-vapor conversion. Chinese Journal of Structural Chemistry, 2024, 43(8): 100380-100380. doi: 10.1016/j.cjsc.2024.100380
10. [10]
  Fei Yin , Erli Yang , Xue Ge , Qian Sun , Fan Mo , Guoqiu Wu , Yanfei Shen . Coupling WO₃₋_x dots-encapsulated metal-organic frameworks and template-free branched polymerization for dual signal-amplified electrochemiluminescence biosensing. Chinese Chemical Letters, 2024, 35(4): 108753-. doi: 10.1016/j.cclet.2023.108753
11. [11]
  Huai-Gui Li , Can-Ming Zhu , Weidong Yuan , Hongyi Chen , Zhengyuan Bo , Chao Deng , Yingguang Zhu , Kang Chen , Qing-Yuan Meng . Stereodivergent reductive C(sp²)-C(sp³) coupling between cycloketone oximes and vinyl halides enabled by tunable photoredox/Ti dual catalysis. Chinese Chemical Letters, 2026, 37(7): 111941-. doi: 10.1016/j.cclet.2025.111941
12. [12]
  Jingrong Huang , Xin Ding , Zihan Lin , Yu Lin , Yongqi Liao , Wang Gu , Fa-Jie Chen , Fen-Er Chen . Bromo nitrile oxide-mediated disulfide formation and capping of N-terminal cysteine in peptides. Chinese Chemical Letters, 2026, 37(6): 111715-. doi: 10.1016/j.cclet.2025.111715
13. [13]
  Dongsheng Yang , Zixin Li , Yaoyao Lian , Ziyao Fu , Tianjiao Li , Pengtao Ma , Guoping Yang . A novel square-shaped Zr-substituted polyoxotungstate for the efficient catalytic oxidation of sulfide to sulfone. Chinese Chemical Letters, 2025, 36(3): 109717-. doi: 10.1016/j.cclet.2024.109717
14. [14]
  Xinlong Han , Huiying Zeng , Chao-Jun Li . Trifluoromethylative homo-coupling of carbonyl compounds. Chinese Chemical Letters, 2025, 36(1): 109817-. doi: 10.1016/j.cclet.2024.109817
15. [15]
  Zhili Li , Qijun Wo , Dongdong Huang , Dezhong Zhou , Lei Guo , Yeqing Mao . Improving gene transfection efficiency of highly branched poly(β-amino ester)s through the in-situ conversion of inactive terminal groups. Chinese Chemical Letters, 2024, 35(8): 109737-. doi: 10.1016/j.cclet.2024.109737
16. [16]
  Ya-Shan Huang , Wen-Juan Tian , Jing-Xuan Zhang , Zhong-Ming Sun . Rational synthesis of highly charged E₉ (E = Ge, Sn) dimer and trimer with Nb/Au bridges. Chinese Chemical Letters, 2026, 37(5): 110827-. doi: 10.1016/j.cclet.2025.110827
17. [17]
  Jielian Yang , Yue Shen , Bing Chen , Qi Wu , Yuemei Liao , Liya Zhou , Jing Luo , Xue Mao , Jin Guo , Binbin Luo , Qi Pang , Chunyan Zhou , Peican Chen , Anxiang Guan . Cu/Ni dual-atom catalysts with charge regulation: Boosting CO₂ electroreduction selectivity via site-specific O/C-terminal asymmetric adsorption. Chinese Chemical Letters, 2026, 37(9): 112638-. doi: 10.1016/j.cclet.2026.112638
18. [18]
  Qijun Tang , Wenguang Tu , Yong Zhou , Zhigang Zou . High efficiency and selectivity catalyst for photocatalytic oxidative coupling of methane. Chinese Journal of Structural Chemistry, 2023, 42(12): 100170-100170. doi: 10.1016/j.cjsc.2023.100170
19. [19]
  Kongchuan Wu , Dandan Lu , Jianbin Lin , Ting-Bin Wen , Wei Hao , Kai Tan , Hui-Jun Zhang . Elucidating ligand effects in rhodium(Ⅲ)-catalyzed arene–alkene coupling reactions. Chinese Chemical Letters, 2024, 35(5): 108906-. doi: 10.1016/j.cclet.2023.108906
20. [20]
  Shengkai Li , Yuqin Zou , Chen Chen , Shuangyin Wang , Zhao-Qing Liu . Defect engineered electrocatalysts for C–N coupling reactions toward urea synthesis. Chinese Chemical Letters, 2024, 35(8): 109147-. doi: 10.1016/j.cclet.2023.109147

Get Citation

PDF

XML

Metrics

PDF Downloads(2)
Abstract views(1675)
HTML views(65)

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

Address：Zhongguancun North First Street 2,100190 Beijing, PR China Tel: +86-010-82449177-888

DownLoad: Full-Size Img PowerPoint

Return