Regioselective Oxidative Chlorination of Arenols Using NaCl and Oxone

被引:25
作者
Uyanik, Muhammet [1 ]
Sahara, Naoto [1 ]
Ishihara, Kazuaki [1 ]
机构
[1] Nagoya Univ, Grad Sch Engn, Chikusa Ku, Furo Cho, Nagoya, Aichi 4648603, Japan
关键词
Chlorination; Dearomatization; Oxidation; Phenols; Chemoselectivity; Regioselectivity; CATALYTIC ASYMMETRIC DEAROMATIZATION; SODIUM-HYPOCHLORITE; IPSO-CHLORINATION; METHYL-ETHER; PHENOL; HALOGENATION; CONVENIENT; POTASSIUM; CHLORIDE; CARBON;
D O I
10.1002/ejoc.201801063
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
We developed a practical and environmentally benign method for the chlorinative dearomatization of arenols using transient electrophilic chlorinating species generated in situ from inexpensive sodium chloride and Oxone as a Cl source and oxidant, respectively, under mild conditions. Moreover, the regioselective chlorination or chlorinative dearomatization of 1-naphthols was also achieved by changing the reaction conditions.
引用
收藏
页码:27 / 31
页数:5
相关论文
共 55 条
[1]  
[Anonymous], 2018, ANGEW CHEM
[2]  
[Anonymous], 2011, ANGEW CHEM INT ED
[3]   REACTION OF HYPOCHLOROUS ACID WITH 2,6-DI-TERT-BUTYLPHENOL AND ITS DERIVATIVES [J].
BANNIKOV, GF ;
VOLEVA, VB ;
NIKIFOROV, GA .
BULLETIN OF THE ACADEMY OF SCIENCES OF THE USSR DIVISION OF CHEMICAL SCIENCE, 1986, 35 (02) :446-448
[4]  
Benedikt R., 1883, MONATSHEFT, V4, P604
[5]  
Curini M, 2000, SYNLETT, P813
[6]  
DENIVELLE L, 1953, CR HEBD ACAD SCI, V237, P340
[7]  
DENIVELLE L, 1961, CR HEBD ACAD SCI, V253, P2711
[8]   Carbon-Phosphorus Bond Formation on Anilines Mediated by a Hypervalent Iodine Reagent [J].
Deruer, Elsa ;
Coulibali, Siomenan ;
Boukercha, Saad ;
Canesi, Sylvain .
JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (22) :11884-11890
[9]   Oxidation of alpha,beta-enones and alkenes with oxone and sodium halides: A convenient laboratory preparation of chlorine and bromine [J].
Dieter, RK ;
Nice, LE ;
Velu, SE .
TETRAHEDRON LETTERS, 1996, 37 (14) :2377-2380
[10]   Chiral Atropisomeric 8,8′-Diiodobinaphthalene for Asymmetric Dearomatizing Spirolactonizations in Hypervalent Iodine Oxidations [J].
Dohi, Toshifumi ;
Sasa, Hirotaka ;
Miyazaki, Keitaro ;
Fujitake, Mihoyo ;
Takenaga, Naoko ;
Kita, Yasuyuki .
JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (22) :11954-11960