Recent Advances in Functionalization of α-C(sp3)-H Centres in Inactivated Ethers through Cross Dehydrogenative Coupling

被引：58
作者：
Batra, Aanchal [1 ]
Singh, Paramjit [2 ,3 ]
Singh, Kamal Nain [2 ,3 ]
机构：
[1] DAV Coll, Dept Chem, Sec 10-D, Chandigarh, India
[2] Panjab Univ, Dept Chem, Chandigarh 160014, India
[3] Panjab Univ, Ctr Adv Studies Chem, Chandigarh 160014, India
来源：
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2017年 / 2017卷 / 26期
关键词：
Saturated cyclic and acyclic ethers; Cross dehydrogenative coupling; Cross-coupling; C-H activation; C-H activation/ functionalization; C-C; C-X bond formation; Radical reactions; Reaction mechanisms; C-C BOND; DIRECT ALPHA-ARYLATION; C(SP(3))-H BONDS; H BONDS; DIRECT ACCESS; OXIDATIVE ACTIVATION; CINNAMIC-ACIDS; CYCLIC ETHERS; N-OXIDES; AMINATION;
D O I：
10.1002/ejoc.201700341
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Carbon-carbon and carbon-heteroatom bond construction through oxidative carbon-hydrogen bond activation has attracted much attention in synthetic organic chemistry. Recently, a variety of reactions of inactivated cyclic ethers (THF, THP and dioxane) and acyclic ethers with various coupling part-ners have been reported. Despite the absence of phenyl rings and high oxidation potentials, these ethers worked efficiently under oxidative conditions. This review focusses on recent reports of C-C and C-heteroatom bond formation in these cyclic and acyclic ethers through cross dehydrogenative coupling.
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收藏
页码：3739 / 3762
页数：24
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共 92 条
  • [1] Cross-dehydrogenative coupling of α-C(sp3)-H of ethers/alkanes with C(sp2)-H of heteroarenes under metal-free conditions
    Ambala, Srinivas
    Thatikonda, Thanusha
    Sharma, Shweta
    Munagala, Gurunadham
    Yempalla, Kushalava Reddy
    Vishwakarma, Ram A.
    Singh, Parvinder Pal
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2015, 13 (46) : 11341 - 11350
  • [2] Cross-Dehydrogenative Coupling of Azoles with α-C(sp3)-H of Ethers and Thioethers under Metal-Free Conditions: Functionalization of H-N Azoles via C-H Activation
    Aruri, Hariprasad
    Singh, Umed
    Sharma, Sumit
    Gudup, Satish
    Bhogal, Mukesh
    Kumar, Sanjay
    Singh, Deepika
    Gupta, Vivek K.
    Kant, Rajni
    Vishwakarma, Ram A.
    Singh, Parvinder Pal
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (03) : 1929 - 1936
  • [3] An efficient and extremely mild method for protecting alcohols as 2-tetrahydrofuranyl ethers
    Barks, JM
    Gilbert, BC
    Parsons, AF
    Upeandran, B
    [J]. TETRAHEDRON LETTERS, 2000, 41 (32) : 6249 - 6252
  • [4] Iron-Catalyzed Oxidative Direct α-C-H Bond Functionalization of Cyclic Ethers: Selective C-O Bond Formation in the Presence of a Labile Aldehyde Group
    Barve, Balaji D.
    Wu, Yang-Chang
    El-Shazly, Mohamed
    Korinek, Michal
    Cheng, Yuan-Bin
    Wang, Jeh-Jeng
    Chang, Fang-Rong
    [J]. ORGANIC LETTERS, 2014, 16 (07) : 1912 - 1915
  • [5] Transition Metal-Free Intermolecular α-C-H Amination of Ethers at Room Temperature
    Buslov, Ivan
    Hu, Xile
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2014, 356 (16) : 3325 - 3330
  • [6] Bu4NI-Catalyzed C-O Bond Formation by Using a Cross-Dehydrogenative Coupling (CDC) Reaction
    Chen, Long
    Shi, Erbo
    Liu, Zhaojun
    Chen, Shulin
    Wei, Wei
    Li, Hong
    Xu, Kai
    Wan, Xiaobing
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (15) : 4085 - 4089
  • [7] Highly efficient metal-free cross-coupling by C-H activation between allylic and active methylenic compounds promoted by DDQ
    Cheng, Dongping
    Bao, Weiliang
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2008, 350 (09) : 1263 - 1266
  • [8] Iron-catalyzed direct α-arylation of ethers with azoles
    Correa, Arkaitz
    Fiser, Bela
    Gomez-Bengoa, Enrique
    [J]. CHEMICAL COMMUNICATIONS, 2015, 51 (69) : 13365 - 13368
  • [9] Copper-catalyzed decarboxylative alkenylation of sp3 C-H bonds with cinnamic acids via a radical process
    Cui, Zili
    Shang, Xiaojie
    Shao, Xiang-Feng
    Liu, Zhong-Quan
    [J]. CHEMICAL SCIENCE, 2012, 3 (09) : 2853 - 2858
  • [10] Coming of Age: Sustainable Iron-Catalyzed Cross-Coupling Reactions
    Czaplik, Waldemar Maximilian
    Mayer, Matthias
    Cvengros, Jan
    Jacobi von Wangelin, Axel
    [J]. CHEMSUSCHEM, 2009, 2 (05) : 396 - 417
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