Catalyst-Free Oxidative [3+2] Cycloaddition of Phenols and Styrenes in the Presence of a 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone/1,1,1,3,3,3-hexafluoropropan-2-ol System

被引:4
作者
Wang, Yunxia [1 ]
Cui, Na [1 ]
Zhao, Yu [1 ]
机构
[1] Northwest Univ, Coll Chem & Mat Sci, Key Lab Synthet & Nat Funct Mol Chem, Minist Educ China, Xian 710127, Shaanxi, Peoples R China
关键词
phenols; styrenes; cyclization; oxidation; dihydrobenzofurans; BIOMIMETIC SYNTHESIS; ANODIC-OXIDATION; ALKENES; DIHYDROBENZOFURANS; RESVERATROL; OLEFINS; FLUOROALCOHOLS; SELECTIVITY; ANALOGS; ACCESS;
D O I
10.1055/s-0036-1589082
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A catalyst-free oxidative [3+2] cycloaddition of phenols and styrenes was developed with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone as the oxidant and 1,1,1,3,3,3-hexafluoropropan-2-ol as the solvent at room temperature. With this method, a broad range of dihydrobenzofurans were efficiently and quickly obtained from readily available phenols and styrenes.
引用
收藏
页码:2619 / 2623
页数:5
相关论文
共 32 条
  • [1] Mechanistic Study of the Biomimetic Synthesis of Flavonolignan Diastereoisomers in Milk Thistle
    Althagafy, Hanan S.
    Meza-Avina, Maria Elena
    Oberlies, Nicholas H.
    Croatt, Mitchell P.
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (15) : 7594 - 7600
  • [2] A new synthetic access to furo[3,2-f]chromene analogues of an antimycobacterial
    Alvey, Luke
    Prado, Soizic
    Huteau, Valerie
    Saint-Joanis, Brigitte
    Michel, Sylvie
    Koch, Michel
    Cole, Stewart T.
    Tillequin, Francois
    Janin, Yves L.
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY, 2008, 16 (17) : 8264 - 8272
  • [3] Photocatalytic Synthesis of Dihydrobenzofurans by Oxidative [3+2] Cycloaddition of Phenols
    Blum, Travis R.
    Zhu, Ye
    Nordeen, Sarah A.
    Yoon, Tehshik P.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (41) : 11056 - 11059
  • [4] Asymmetric biomimetic oxidations of phenols using oxazolidines as chiral auxiliaries: the enantioselective synthesis of (+)- and (-)-dehydrodiconiferyl alcohol
    Bruschi, Maurizio
    Orlandi, Marco
    Rindone, Bruno
    Rummakko, Petteri
    Zoia, Luca
    [J]. JOURNAL OF PHYSICAL ORGANIC CHEMISTRY, 2006, 19 (8-9) : 592 - 596
  • [5] Cerium ammonium nitrate-mediated the oxidative dimerization of p-alkenylphenols: a new synthesis of substituted (±)-trans-dihydrobenzofurans
    Chen, Po-Yuan
    Wu, Yi-Hua
    Hsu, Mon-Huei
    Wang, Tzu-Pin
    Wang, Eng-Chi
    [J]. TETRAHEDRON, 2013, 69 (02) : 653 - 657
  • [6] Dihydrobenzofuran synthesis by an anodic [3+2] cycloaddition of phenols and unactivated alkenes
    Chiba, K
    Fukuda, M
    Kim, S
    Kitano, Y
    Tada, M
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (20) : 7654 - 7656
  • [7] Recent Advances in Oxidative Cycloaddition Reactions of Phenols with Olefins
    Cui, Na
    Zhao, Yu
    Wang, Yunxia
    [J]. CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2017, 37 (01) : 20 - 30
  • [8] PHENOL AND ANILINE OXIDATIVE COUPLING WITH ALKENES BY USING HYPERVALENT IODINE DIMER FOR THE RAPID ACCESS TO DIHYDROBENZOFURANS AND INDOLINES
    Dohi, Toshifumi
    Toyoda, Yosuke
    Nakae, Tomofumi
    Koseld, Daichi
    Kubo, Hiroko
    Kamitanaka, Tohru
    Kita, Yasuyuki
    [J]. HETEROCYCLES, 2015, 90 (01) : 631 - 644
  • [9] Fluoroalcohols: versatile solvents in hypervalent iodine chemistry and syntheses of diaryliodonium(III) salts
    Dohi, Toshifumi
    Yamaoka, Nobutaka
    Kita, Yasuyuki
    [J]. TETRAHEDRON, 2010, 66 (31) : 5775 - 5785
  • [10] Reactivity of naphthol towards nucleophiles in anodic oxidation
    El-Seedi, HR
    Yamamura, S
    Nishiyama, S
    [J]. TETRAHEDRON, 2002, 58 (37) : 7485 - 7489