Iron-Catalyzed π-Activated C-O Ether Bond Cleavage with C-C and C-H Bond Formation

被引:24
|
作者
Fan, Xiaohui [1 ,2 ]
Cui, Xiao-Meng [1 ]
Guan, Yong-Hong [1 ]
Fu, Lin-An [1 ]
Lv, Hao [1 ]
Guo, Kun [1 ]
Zhu, Hong-Bo [1 ]
机构
[1] Lanzhou Jiaotong Univ, Sch Chem & Biol Engn, Lanzhou 730070, Peoples R China
[2] BNLMS, Beijing 100190, Peoples R China
基金
中国国家自然科学基金;
关键词
Synthetic methods; Allylation; C-O activation; C-C coupling; Hydrogen transfer; Iron; CARBON-CARBON BONDS; BENZYLIC ALCOHOLS; OXYGEN BOND; ALLYLATION; NUCLEOPHILES; REAGENTS; ALKYLATION; ALDEHYDES; EFFICIENT; ARENES;
D O I
10.1002/ejoc.201301372
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A novel and efficient allylic alkylation reaction between -activated ethers and allylsilane was realized under mild conditions through iron(III)-catalyzed Csp3-O ether bond cleavage. The present protocol provides an attractive approach for the construction of sp(3)-sp(3) C-C bonds and can be potentially applied for the selective reduction of benzyl and allyl ethers to their corresponding hydrocarbon compounds by using triethylsilane as a hydride-transfer reagent.
引用
收藏
页码:498 / 501
页数:4
相关论文
共 50 条
  • [1] Iron-Catalyzed C-C Bond Cleavage and C-N Bond Formation
    Li, Wenjuan
    Zheng, Xiaojian
    Li, Zhiping
    ADVANCED SYNTHESIS & CATALYSIS, 2013, 355 (01) : 181 - 190
  • [2] Iron-catalyzed C-C bond activation/C-O bond formation: Direct conversion of ketones to esters
    Arzumanyan, Ashot V.
    TETRAHEDRON LETTERS, 2017, 58 (50) : 4667 - 4671
  • [3] Iron-catalyzed azidation of cyclobutanol by C-C bond cleavage
    Liu, Xiaoyuan
    Wang, Limei
    Zhan, Jincheng
    Sun, Shutao
    Liu, Lei
    Li, Wei
    Wan, Qian
    TETRAHEDRON LETTERS, 2024, 140
  • [4] Iron-Catalyzed C-C Bond Formation via Chelation-Assisted C-H Activation
    Yoshikai, Naohiko
    ISRAEL JOURNAL OF CHEMISTRY, 2017, 57 (12) : 1117 - 1130
  • [5] Mechanistic Insights into Iron-Catalyzed C-H Bond Activation and C-C Coupling
    Brewer, Samantha M.
    Schwartz, Timothy M.
    Mekhail, Magy A.
    Turan, Lara S.
    Prior, Timothy J.
    Hubin, Timothy J.
    Janesko, Benjamin G.
    Green, Kayla N.
    ORGANOMETALLICS, 2021, 40 (15) : 2467 - 2477
  • [6] Iron-catalyzed C-C bond formation by direct functionalization of C-H bonds adjacent to heteroatoms
    Li, Zhiping
    Yu, Rong
    Li, Haijun
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (39) : 7497 - 7500
  • [7] Catalytic C-C Bond Formation by C-H Functionaliza C-C Bond Cleavage Preface
    Dong, Guangbin
    TETRAHEDRON, 2016, 72 (22) : 2717 - 2717
  • [8] Low-Valent Iron-Catalyzed C-C Bond Formation-Addition, Substitution, and C-H Bond Activation
    Nakamura, Eiichi
    Yoshikai, Naohiko
    JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (18): : 6061 - 6067
  • [9] Iron-Catalyzed C-C Single-Bond Cleavage of Alcohols
    Liu, Wei
    Wu, Qiang
    Wang, Miao
    Huang, Yahao
    Hu, Peng
    ORGANIC LETTERS, 2021, 23 (21) : 8413 - 8418
  • [10] Palladium nanoparticles catalyzed C-C, C-N and C-O bond formation Via C-H activation
    Saha, Rajib
    Sekar, G.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2018, 256