One-Pot Access to Cinnamates via Direct Oxidative C-H Transformation of Allylarenes

被引：10
|
作者：
Chang, Meng-Yang [1 ]
Lin, Shin-Ying [1 ]
Chan, Chieh-Kai [1 ]
机构：
[1] Kaohsiung Med Univ, Dept Med & Appl Chem, Kaohsiung 807, Taiwan
来源：
SYNLETT | 2013年 / 24卷 / 04期
关键词：
allylarenes; C-H esterification; cinnamates; ALLYLIC OXIDATION; BOND FUNCTIONALIZATION; DDQ; AMINATION; CYCLIZATION; ACTIVATION; ALCOHOLS; ALKENES; ESTERS; CINNAMALDEHYDES;
D O I：
10.1055/s-0032-1318146
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A highly selective combination of ruthenium complex and oxidant, which catalyzes the oxidative C-H esterification of allylarenes to the corresponding bis-(E)-cinnamates and (E)-cinnamates, is described. The one-pot route was carried out by olefinic migration of allylarenes with RuCl2(PPh3)(3) and DDQ-mediated allylic oxidation of the resulting internal alkenes with various alcohols in good yields.
引用
收藏
页码：487 / 490
页数：4
相关论文
共 50 条
  • [1] Iron-Facilitated Direct Oxidative C-H Transformation of Allylarenes or Alkenes to Alkenyl Nitriles
    Qin, Chong
    Jiao, Ning
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (45) : 15893 - 15895
  • [2] Synthesis of Pyrazolofuropyrazine via One-Pot SNAr Reaction and Intramolecular Direct C-H Arylation
    Fuse, Shinichiro
    Inaba, Megumi
    Sato, Shinichi
    Joshi, Manjusha
    Nakamura, Hiroyuki
    SYNTHESIS-STUTTGART, 2018, 50 (07): : 1493 - 1498
  • [3] Copper-catalyzed one-pot oxidative amidation of alcohol to amide via C-H activation
    Gu, Jiajia
    Fang, Zheng
    Yang, Yuhang
    Yang, Zhao
    Wan, Li
    Li, Xin
    Wei, Ping
    Guo, Kai
    RSC ADVANCES, 2016, 6 (92) : 89413 - 89416
  • [4] An efficient one-pot synthesis of 2-aminothiazoles via electrochemically oxidative α-C-H functionalization of ketones with thioureas
    Li, Pei
    Yang, Shang-Feng
    Fang, Zi-Lin
    Cui, Hao-Ran
    Liang, Sen
    Tian, Hong-Yu
    Sun, Bao-Guo
    Zeng, Cheng-Chu
    JOURNAL OF ENVIRONMENTAL CHEMICAL ENGINEERING, 2022, 10 (03):
  • [5] One-Pot C-H Functionalization of Arenes by Diaryliodonium Salts
    Reitti, Marcus
    Villo, Piret
    Olofsson, Berit
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (31) : 8928 - 8932
  • [6] Organocatalytic Enantioselective One-pot Synthesis of Dihydrocoumarins via C-H Oxidation and Cyclization Cascade
    Kim, Kyeong Seop
    Kim, Dae Young
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2023, 12 (10)
  • [7] One-Pot Synthesis of Amides from Aldehydes and Amines via C-H Bond Activation
    Cadoni, Roberta
    Porcheddu, Andrea
    Giacomelli, Giampaolo
    De Luca, Lidia
    ORGANIC LETTERS, 2012, 14 (19) : 5014 - 5017
  • [8] One-Pot Synthesis of Dihydrobenzo[a]fluorenes via Cascade C-H Annulation of Thiobenzamide with Alkynes
    Pu, Xingwen
    Fu, Zhangyi
    Yang, Yudong
    Wu, Di
    Deng, Pengchi
    Lan, Jingbo
    JOURNAL OF ORGANIC CHEMISTRY, 2024, 89 (18): : 13110 - 13116
  • [9] A novel catalytic one-pot synthesis of carbazoles via consecutive amination and C-H activation
    Bedford, RB
    Cazin, CSJ
    CHEMICAL COMMUNICATIONS, 2002, (20) : 2310 - 2311
  • [10] Copper-catalyzed one-pot synthesis of propargylamines via C-H activation in PEG
    Zhang, Qiang
    Chen, Jiu-Xi
    Gao, Wen-Xia
    Ding, Jin-Chang
    Wu, Hua-Yue
    APPLIED ORGANOMETALLIC CHEMISTRY, 2010, 24 (11) : 809 - 812
12345