Iron-facilitated direct oxidative C-H transformation of allyl arenes to alkenyl aldehydes

被引：15
|
作者：
Wang, Teng [1 ,2 ]
Xiang, Shi-Kai [1 ]
Qin, Chong [1 ]
Ma, Jun-An [2 ]
Zhang, Li-He [1 ]
Jiao, Ning [1 ,3 ]
机构：
[1] Peking Univ, State Key Lab Nat & Biomimet Drugs, Beijing 100191, Peoples R China
[2] Tianjin Univ, Dept Chem, Tianjin 300072, Peoples R China
[3] Chinese Acad Sci, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China
来源：
TETRAHEDRON LETTERS | 2011年 / 52卷 / 25期
基金：
美国国家科学基金会;
关键词：
BOND FUNCTIONALIZATION; TERMINAL ALKENES; AMINATION; ALKYLATION; CATALYST; ACTIVATION; HETEROATOM; MECHANISM; ADJACENT; ETHERS;
D O I：
10.1016/j.tetlet.2011.04.041
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A direct oxidative approach to alkenyl aldehydes from allyl arenes via allyl sp(3) C-H functionalization was disclosed. An inexpensive iron catalyst was employed to facilitate this transformation. The mechanistic studies indicate that the cleavage of the allyl sp(3) C-H bond is involved in the rate-determining step. (C) 2011 Elsevier Ltd. All rights reserved.
引用
收藏
页码：3208 / 3211
页数：4
相关论文
共 50 条
  • [31] Regioselective C-H Amidation of (Alkyl)arenes by Iron(II) Catalysis
    Ding, Yao
    Zhang, Shen-Yuan
    Chen, Yu-Chen
    Fan, Shuai-Xin
    Tian, Jie-Sheng
    Loh, Teck-Peng
    ORGANIC LETTERS, 2019, 21 (08) : 2736 - 2739
  • [32] Regioselective C-H Thiocyanation of Arenes by Iron(III) Chloride Catalysis
    Waddell, Lachlan J. N.
    Senkans, Maisie R.
    Sutherland, Andrew
    JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (11): : 7208 - 7218
  • [33] Photoredox ketone catalysis for the direct C-H imidation and acyloxylation of arenes
    Tripathi, Chandra Bhushan
    Ohtani, Tsuyoshi
    Corbett, Michael T.
    Ooi, Takashi
    CHEMICAL SCIENCE, 2017, 8 (08) : 5622 - 5627
  • [34] Direct C-H Radiocyanation of Arenes via Organic Photoredox Catalysis
    Chen, Wei
    Wu, Xuedan
    McManus, Joshua B.
    Bida, Gerald T.
    Li, Kang-Po
    Wu, Zhanhong
    Nicewicz, David A.
    Li, Zibo
    ORGANIC LETTERS, 2022, 24 (50) : 9316 - 9321
  • [35] Direct C-H arylation of simple arenes: Ligand effect and mechanism
    Hong, Soon Hyeok
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2017, 254
  • [36] Manganese(I)-Catalyzed Direct C-H Allylation of Arenes with Allenes
    Chen, Shi-Yong
    Li, Qingjiang
    Wang, Honggen
    JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (20): : 11173 - 11181
  • [37] C-H functionalization of (hetero)arenes: Direct selanylation mediated by Selectfluor
    Belladona, Andrei L.
    Cervo, Rodrigo
    Alves, Diego
    Barcellos, Thiago
    Cargnelutti, Roberta
    Schumacher, Ricardo F.
    TETRAHEDRON LETTERS, 2020, 61 (26)
  • [38] Base-Mediated Direct C-H Germylation of Heteroarenes and Arenes
    Dahiya, Amit
    Schoenebeck, Franziska
    ORGANIC LETTERS, 2021, 23 (15) : 6010 - 6013
  • [39] Iron-mediated oxidative C-H coupling of arenes and alkenes directed by sulfur: an expedient route to dihydrobenzofurans
    Cavanagh, Craig W.
    Aukland, Miles H.
    Laurent, Quentin
    Hennessy, Alan
    Procter, David J.
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2016, 14 (23) : 5286 - 5292
  • [40] Palladium-Catalyzed Oxidative Direct ortho-C-H Acylation of Arenes with Aldehydes under Aqueous Conditions
    Xiao, Fuhong
    Chen, Shuqing
    Huang, Huawen
    Deng, Guo-Jun
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2015, 2015 (36) : 7919 - 7925
12345