Citation: Wen Hui Zhong, Ying Na Cui, Shen Min Li, Ying Ping Jia, Jing Mei Yin. The carbonylation of phenyl bromide and its derivatives under visible light irradiation[J]. Chinese Chemical Letters, ;2012, 23(1): 29-32. doi: 10.1016/j.cclet.2011.09.024 shu

The carbonylation of phenyl bromide and its derivatives under visible light irradiation

Liaoning Key Laboratory of Bio-organic Chemistry, Dalian University, Dalian 116622, China

Received Date: 7 June 2011

The carbonylation of phenyl bromide catalyzed by Co(OAc)₂ has been investigated with PhCOPh as a sensitizer under visible light in the presence of basic additive. With strong base CH₃ONa, PhCOOCH₃ is produced in 70% yield with 100% selectivity, the similar results are also obtained with a stronger base (CH₃)₃CONa. However, with another strong base NaOH, the yield of the ester is only 40%. On the other hand, with weak base NaOAc or (n-C₄H₉)₃N, phenyl bromide cannot be carbonylated. The results of carbonylation of the six substituted phenyl bromides suggest that the activities of o, m, p-BrC₆H₄CH₃ are similar to phenyl bromide, while the activities of o, m, p-BrC₆H₄Cl are higher with the high yields (≥ 93%) of the corresponding chloro-esters. In addition, the relative position of bromine and chlorine or methyl on phenyl ring has little effect on the activity of the carbonylation.
- Carbonylation,
- Phenyl bromide,
- o, m, p-Bromotoluene,
- o, m, p-Bromochlorobenzene,
- Visible light
1. [1]
  Lei Shen , Yang Zhang , Linlin Zhang , Chuanwang Liu , Zhixian Ma , Kangjiang Liang , Chengfeng Xia . Phenylhydrazone anions excitation for the photochemical carbonylation of aryl iodides with aldehydes. Chinese Chemical Letters, 2024, 35(4): 108742-. doi: 10.1016/j.cclet.2023.108742
2. [2]
  Lang Gao , Cen Zhou , Rui Wang , Feng Lan , Bohang An , Xiaozhou Huang , Xiao Zhang . Unveiling inverse vulcanized polymers as metal-free, visible-light-driven photocatalysts for cross-coupling reactions. Chinese Chemical Letters, 2024, 35(4): 108832-. doi: 10.1016/j.cclet.2023.108832
3. [3]
  Liangbo Zhang , Jun Cheng , Yahui Shi , Kunjie Hou , Qi An , Jingyi Li , Baohui Cui , Fei Chen . Efficient removal of tetracycline hydrochloride by ZnO/HNTs composites under visible light: Kinetics, degradation pathways and mechanism. Chinese Chemical Letters, 2025, 36(7): 110400-. doi: 10.1016/j.cclet.2024.110400
4. [4]
  Ting Zhang , Baojing Huang , Hong Huang , Ailing Yan , Shiqiang Lu , Xufang Qian . Visible light boosted Fenton-like reaction of carbon dot-Fe(Ⅲ) complex: Kinetics and mechanism insights. Chinese Chemical Letters, 2025, 36(11): 110885-. doi: 10.1016/j.cclet.2025.110885
5. [5]
  Wenjuan Liu , Shanshan Zhang , Yu Wang , Bin Fang , Weirui Wang , Shujing Song , Tomohiro Hakozaki . Three-channel imaging reveals the comprehensive protein modifications and their impact on skin appearance induced by multiple stimuli. Chinese Chemical Letters, 2025, 36(6): 111182-. doi: 10.1016/j.cclet.2025.111182
6. [6]
  Hefei Yang , Le-Cheng Wang , Xiao-Feng Wu . Sustainable carbonylative transformation of alkyl iodides to amides via crosslinking of EDA and XAT. Chinese Chemical Letters, 2025, 36(9): 110843-. doi: 10.1016/j.cclet.2025.110843
7. [7]
  Zhi-Peng Bao , Hefei Yang , Ru-Han A , Yuanrui Wang , Xiao-Feng Wu . Carbonylative five-component synthesis of amides and esters with α-quaternary carbon center. Chinese Chemical Letters, 2025, 36(11): 111150-. doi: 10.1016/j.cclet.2025.111150
8. [8]
  Xiang Li , Beibei Zhang , Zhixiang Wang , Xiangyu Chen . Organocatalyzed iodine-mediated reversible-deactivation radical polymerization via photoinduced charge transfer complex catalysis. Chinese Chemical Letters, 2025, 36(6): 110383-. doi: 10.1016/j.cclet.2024.110383
9. [9]
  Ping Lu , Baoyin Du , Ke Liu , Ze Luo , Abiduweili Sikandaier , Lipeng Diao , Jin Sun , Luhua Jiang , Yukun Zhu . Heterostructured In2O3/In2S3 hollow fibers enable efficient visible-light driven photocatalytic hydrogen production and 5-hydroxymethylfurfural oxidation. Chinese Journal of Structural Chemistry, 2024, 43(8): 100361-100361. doi: 10.1016/j.cjsc.2024.100361
10. [10]
  Guanyang Zeng , Xingqiang Liu , Liangqiao Wu , Zijie Meng , Debin Zeng , Changlin Yu . Novel visible-light-driven I- doped Bi2O2CO3 nano-sheets fabricated via an ion exchange route for dye and phenol removal. Chinese Journal of Structural Chemistry, 2024, 43(12): 100462-100462. doi: 10.1016/j.cjsc.2024.100462
11. [11]
  Jijoe Samuel Prabagar , Kumbam Lingeshwar Reddy , Dong-Kwon Lim . Visible-light responsive gold nanoparticle and nano-sized Bi2O3-x sheet heterozygote structure for efficient photocatalytic conversion of N2 to NH3. Chinese Journal of Structural Chemistry, 2025, 44(4): 100564-100564. doi: 10.1016/j.cjsc.2025.100564
12. [12]
  Hualin Jiang , Wenxi Ye , Huitao Zhen , Xubiao Luo , Vyacheslav Fominski , Long Ye , Pinghua Chen . Novel 3D-on-2D g-C₃N₄/AgI._x._y heterojunction photocatalyst for simultaneous and stoichiometric production of H₂ and H₂O₂ from water splitting under visible light. Chinese Chemical Letters, 2025, 36(2): 109984-. doi: 10.1016/j.cclet.2024.109984
13. [13]
  Ruiheng Liang , Huizhong Wu , Zhongzheng Hu , Ge Song , Xuyang Zhang , Omotayo A. Arotiba , Minghua Zhou . Hierarchical Fe-Bi/Bi₇O₉I₃/OVs microspheres coupled with natural air diffusion electrode to achieve efficient heterogeneous visible-light-driven photoelectro-Fenton degradation of tetracycline without aeration. Chinese Chemical Letters, 2025, 36(4): 110136-. doi: 10.1016/j.cclet.2024.110136
14. [14]
  Jingyuan Yang , Xinyu Tian , Liuzhong Yuan , Yu Liu , Yue Wang , Chuandong Dou . Enhancing stability of diradical polycyclic hydrocarbons via P=O-attaching. Chinese Chemical Letters, 2024, 35(8): 109745-. doi: 10.1016/j.cclet.2024.109745
15. [15]
  Xuhui Fan , Fan Wang , Mengjiao Li , Faiza Meharban , Yaying Li , Yuanyuan Cui , Xiaopeng Li , Jingsan Xu , Qi Xiao , Wei Luo . Visible light excitation on CuPd/TiN with enhanced chemisorption for catalyzing Heck reaction. Chinese Chemical Letters, 2025, 36(1): 110299-. doi: 10.1016/j.cclet.2024.110299
16. [16]
  Jia Peng , Guo-Ping Luo , Chao Wu , Congyang Wang . Visible light-induced deuteration of arenes via thianthrenation. Chinese Chemical Letters, 2025, 36(8): 111255-. doi: 10.1016/j.cclet.2025.111255
17. [17]
  Xia Mi , Chaoyang Wang , Jingyu Zhang , Remi Chauvin , Xiuling Cui . Recent progress in the visible-light-promoted synthesis of phenanthridines. Chinese Chemical Letters, 2025, 36(11): 111485-. doi: 10.1016/j.cclet.2025.111485
18. [18]
  Hui-Xian Jiang , Zhi-Tao Liu , Pei Xu , Xu Zhu . Synthetic application of oxalate salts for visible-light-induced radical transformations. Chinese Chemical Letters, 2025, 36(12): 111224-. doi: 10.1016/j.cclet.2025.111224
19. [19]
  Tingting Liu , Pengfei Sun , Wei Zhao , Yingshuang Li , Lujun Cheng , Jiahai Fan , Xiaohui Bi , Xiaoping Dong . Magnesium doping to improve the light to heat conversion of OMS-2 for formaldehyde oxidation under visible light irradiation. Chinese Chemical Letters, 2024, 35(4): 108813-. doi: 10.1016/j.cclet.2023.108813
20. [20]
  Zhanhui Yang , Jiaxi Xu . (m+n+…) or [m+n+…]cycloaddition?. University Chemistry, 2025, 40(3): 387-389. doi: 10.12461/PKU.DXHX202406032

Get Citation

PDF

XML

Metrics

PDF Downloads(3)
Abstract views(1152)
HTML views(30)

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