Efficient Synthesis of p-Quinols Using Catalytic Hypervalent Iodine Oxidation of 4-Arylphenols with 4-Iodophenoxyacetic Acid and Oxone®

被引：32

作者：

Yakura, Takayuki ^{[1
]}

Omoto, Masanori ^{[1
]}

机构：

[1] Toyama Univ, Grad Sch Med & Pharmaceut Sci, Toyama 9300194, Japan

来源：

CHEMICAL & PHARMACEUTICAL BULLETIN | 2009年 / 57卷 / 06期

关键词：

p-quinol; 4-iodophenoxyacetic acid; Oxone (R); catalytic hypervalent iodine oxidation; 4-arylphenol; M-CHLOROPERBENZOIC ACID; POLYMER-SUPPORTED IBX; RAY CRYSTAL-STRUCTURE; IN-SITU GENERATION; TOLUENESULFONIC ACID; ALPHA-TOSYLOXYKETONES; OXIDIZING SYSTEM; SINGLET OXYGEN; KETONES; PHENOLS;

D O I：

10.1248/cpb.57.643

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

Efficient synthesis of p-quinols (2) using catalytic hypervalent iodine oxidation of 4-arylphenols (1) with 4-iodophenoxyacetic acid (3) and Oxone (R) was developed. Reaction of I with a catalytic amount of 3 in the presence of Oxone (R) as a co-oxidant in tetrahydrofuran or 1,4-dioxane-water gave the corresponding 2 in excellent yields.

引用

页码：643 / 645

页数：3

共 18 条

[1] Catalytic Hypervalent Iodine Oxidation of p-Dialkoxybenzenes to p-Quinones Using 4-Iodophenoxyacetic Acid and Oxone®
Yakura, Takayuki
Yamauchi, Yu
Tian, Yuan
Omoto, Masanori
CHEMICAL & PHARMACEUTICAL BULLETIN, 2008, 56 (11) : 1632 - 1634
[2] Catalytic Hypervalent Iodine Oxidation Using 4-Iodophenoxyacetic Acid and Oxone®: Oxidation of p-Alkoxyphenols to p-Benzoquinones
Yakura, Takayuki
Tian, Yuan
Yamauchi, Yu
Omoto, Masanori
Konishi, Tatsuya
CHEMICAL & PHARMACEUTICAL BULLETIN, 2009, 57 (03) : 252 - 256
[3] A novel catalytic hypervalent iodine oxidation of p-alkoxyphenols to p-quinones using 4-iodophenoxyacetic acid and oxone
Yakura, Takayuki
Konishi, Tatsuya
SYNLETT, 2007, (05) : 765 - 768
[4] Hypervalent iodine oxidation of phenol derivatives using a catalytic amount of 4-iodophenoxyacetic acid and Oxone® as a co-oxidant
Yakura, Takayuki
Omoto, Masanori
Yamauchi, Yu
Tian, Yuan
Ozono, Ayaka
TETRAHEDRON, 2010, 66 (31) : 5833 - 5840
[5] A SIMPLE AND EFFICIENT PROCEDURE FOR THE PREPARATION OF P-QUINOLS BY HYPERVALENT IODINE OXIDATION OF PHENOLS AND PHENOL TRIPROPYLSILYL ETHERS
MCKILLOP, A
MCLAREN, L
TAYLOR, RJK
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1994, (15): : 2047 - 2048
[6] Oxidation of 4-arylphenol trimethylsilyl ethers to p-arylquinols using hypervalent iodine(III) reagents
Felpin, Francois-Xavier
TETRAHEDRON LETTERS, 2007, 48 (03) : 409 - 412
[7] A Novel Synthesis of 4-Acetoxyl 5(4H)-Oxazolones by Direct α-Oxidation of N-Benzoyl Amino-Acid Using Hypervalent Iodine
Wen, Gang
Zhang, Wen-Xuan
Wu, Song
MOLECULES, 2017, 22 (07):
[8] Oxidative Cyclization of β,γ-Unsaturated Carboxylic Acids Using Hypervalent Iodine Reagents: An Efficient Synthesis of 4-Substituted Furan-2-ones
Kiyokawa, Kensuke
Takemoto, Kenta
Yahata, Shunsuke
Kojima, Takumi
Minakata, Satoshi
SYNTHESIS-STUTTGART, 2017, 49 (13): : 2907 - 2912
[9] Facile and efficient synthesis of 7,10-dihydroxy-6H-pyrazolo[4,5,1-de]acridin-6-one via hypervalent iodine oxidation
Kato, N
Sugaya, T
Mimura, T
Ikuta, M
Kato, S
Kuge, Y
Tomioka, S
Kasai, M
SYNTHESIS-STUTTGART, 1997, (06): : 625 - &
[10] HYPERVALENT IODINE OXIDATION OF 2-METHYL-4-QUINOLONES USING [HYDROXY(TOSYLOXY)IODO]BENZENE - SYNTHESIS OF 2-METHYL-3-IODO-4-PHENOXYQUINOLINES VIA NOVEL MONOCARBONYL IODONIUM YLIDES
PRAKASH, O
KUMAR, D
SAINI, RK
SINGH, SP
TETRAHEDRON LETTERS, 1994, 35 (24) : 4211 - 4214

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