Ru(II)-Catalyzed Decarbonylative Alkylation and Annulations of Benzaldehydes with Iodonium Ylides under Chelation Assistance

被引：27
|
作者：
Li, Xiang [1 ]
Shen, Yang [1 ]
Zhang, Guodong [2 ]
Zheng, Xin [1 ]
Zhao, Qing [1 ]
Song, Zihe [1 ]
机构：
[1] Shaanxi Univ Sci & Technol, Coll Chem & Chem Engn, Shaanxi Key Lab Chem Addit Ind, Xian 710021, Shaanxi, Peoples R China
[2] Yangzhou Univ, Coll Chem & Chem Engn, 180 Siwangting Rd, Yangzhou 225002, Jiangsu, Peoples R China
来源：
ORGANIC LETTERS | 2022年 / 24卷 / 29期
基金：
中国国家自然科学基金;
关键词：
C-H ACTIVATION; DIVERGENT SYNTHESIS; INDOLE ALKALOIDS; FORMAL SYNTHESIS; SALICYLALDEHYDES; CONSTRUCTION; DIBENZOFURANS; ALDEHYDES; CHROMONES; ALKYNES;
D O I：
10.1021/acs.orglett.2c01843
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A Ru(II)-catalyzed decarbonylative alkylation and annulation of salicylaldehydes and 2-aminobenzaldehydes with iodonium ylides has been developed for the synthesis of dibenzo[b,d]furans and NH-free carbazolones. The reaction proceeds smoothly under mild conditions with a low catalyst loading and a broad substrate compatibility. Notably, hydroxy and free amino groups were demonstrated to be the effective directing groups, enabling the successful aldehyde C-H bond activation and subsequent decarbonylation and annulation under the inexpensive Ru(II) catalyst.
引用
收藏
页码：5281 / 5286
页数：6
相关论文
共 50 条
  • [21] Ir(III)-catalyzed C-H alkynylation of arenes under chelation assistance
    Tang, Guo-Dong
    Pan, Cheng-Ling
    Xie, Fang
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2016, 14 (10) : 2898 - 2904
  • [22] NNN Pincer Ru(II)-Complex-Catalyzed α-Alkylation of Ketones with Alcohols
    Cao, Xiao-Niu
    Wan, Xiao-Min
    Yang, Fa-Liu
    Li, Ke
    Hao, Xin-Qi
    Shao, Tian
    Zhu, Xinju
    Song, Mao-Ping
    JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (07): : 3657 - 3668
  • [23] Fe-Catalyzed decarbonylative alkylation-peroxidation of alkenes with aliphatic aldehydes and hydroperoxide under mild conditions
    Wu, Chuan-Shuo
    Li, Rong
    Wang, Qi-Qiang
    Yang, Luo
    GREEN CHEMISTRY, 2019, 21 (02) : 269 - 274
  • [24] Rhodium(II)-catalyzed reaction of iodonium ylides with electron-deficient and conjugated alkynes: Efficient synthesis of substituted furans
    Lee, Yong Rok
    Yoon, Sang Heum
    SYNTHETIC COMMUNICATIONS, 2006, 36 (14) : 1941 - 1951
  • [25] Ru(II)-catalyzed P(III)-assisted C8-alkylation of naphthphosphines
    Ma, Wen-Tao
    Huang, Mao-Gui
    Fu, Yueliuting
    Wang, Zhong-Hui
    Tao, Jun-Yang
    Li, Jia-Wei
    Liu, Yue-Jin
    Zeng, Ming-Hua
    CHEMICAL COMMUNICATIONS, 2022, 58 (51) : 7152 - 7155
  • [26] Copper-catalyzed C-H alkylation of 8-aminoquinolines via 8-amide chelation assistance
    Xia, Xiao-Feng
    Zhu, Su-Li
    Gu, Zhen
    Wang, Haijun
    RSC ADVANCES, 2015, 5 (37): : 28892 - 28895
  • [27] Rhodium-Catalyzed Alkylation of C-H Bonds in Aromatic Amides with Styrenes via Bidentate-Chelation Assistance
    Shibata, Kaname
    Yamaguchi, Takuma
    Chatani, Naoto
    ORGANIC LETTERS, 2015, 17 (14) : 3584 - 3587
  • [28] Rh(III)- and Ir(III)-Catalyzed C-H Alkynylation of Arenes under Chelation Assistance
    Xie, Fang
    Qi, Zisong
    Yu, Songjie
    Li, Xingwei
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (12) : 4780 - 4787
  • [29] Ruthenium(II)-Catalyzed Homocoupling of Weakly Coordinating Sulfoxonium Ylides via C-H Activation/Annulations: Synthesis of Functionalized Isocoumarins
    Zhou, Ming-Dong
    Peng, Zhen
    Wang, He
    Wang, Zhao-Hui
    Hao, Da-Jin
    Li, Lei
    ADVANCED SYNTHESIS & CATALYSIS, 2019, 361 (22) : 5191 - 5197
  • [30] Decarbonylative Issues Involved in Ru(II)-catalyzed [6+2-1] Annulation Reaction of Hydroxychromone with Alkyne: A DFT Study
    Ling, Baoping
    Wang, Jiarong
    Liu, Yuxia
    Jiang, Yuan-Ye
    Liu, Peng
    Feng, Jin
    Bi, Siwei
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2021, 2021 (02) : 266 - 273
12345