Aerobic Oxysulfonylation of Alkenes Leading to Secondary and Tertiary β-Hydroxysulfones

被引：392

作者：

Lu, Qingquan ^{[1
]}

Zhang, Jian ^{[1
]}

Wei, Fuliang ^{[3
]}

Qi, Yue ^{[1
]}

Wang, Huamin ^{[1
]}

Liu, Zhiliang ^{[1
]}

Lei, Aiwen ^{[1
,2
]}

机构：

[1] Wuhan Univ, Coll Chem & Mol Sci, Wuhan 430072, Peoples R China

[2] Chinese Acad Sci, Lanzhou Inst Chem Phys, State Key Lab Oxo Synth & Select Oxidat, Lanzhou 730000, Peoples R China

[3] Nanjing Univ Posts & Telecommun, Sch Mat Sci & Engn, Nanjing, Jiangsu, Peoples R China

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2013年 / 52卷 / 28期

基金：

中国国家自然科学基金;

关键词：

alkenes; dioxygen activation; oxidative difunctionalization; sulfinic acids; -hydroxysulfones; BAKERS-YEAST REDUCTION; MOLECULAR-OXYGEN; KETO-SULFONES; METAL-FREE; CATALYZED OXIDATION; DIOXYGEN ACTIVATION; UNSATURATED-HYDROCARBONS; CONVENIENT SYNTHESIS; CARBONYL-COMPOUNDS; HYDROXY SULFONES;

D O I：

10.1002/anie.201301634

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

New channel! A novel and attractive dioxygen activation by sulfinic acids was explored that is capable of performing efficiently without the assistance of transition metals or radical initiators. This reaction furnishes secondary and tertiary β-hydroxysulfones under mild conditions; β-hydroperoxysulfone was isolated as an important intermediate. Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

引用

页码：7156 / 7159

页数：4

共 78 条

[31] Synthesis of Imidazo[1,2-a]pyridines: "Water-Mediated" Hydroamination and Silver-Catalyzed Aminooxygenation [J].

Mohan, Darapanem Chandra ;

Rao, Sadu Nageswara ;

Adimurthy, Subbarayappa .

JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (03) :1266-1272

[32] Cerium(IV) ammonium nitrate (CAN)-mediated sulfonylation of styrenes: some interesting observations [J].

Nair, V ;

Augustine, A ;

Panicker, SB ;

Suja, TD ;

Mathai, S .

RESEARCH ON CHEMICAL INTERMEDIATES, 2003, 29 (02) :213-226

[33] MANGANESE(III)-BASED OXIDATIVE FREE-RADICAL REACTION OF ALPHA-ALLYL-BETA-KETO ESTER WITH MOLECULAR-OXYGEN [J].

OHSHIMA, T ;

SODEOKA, M ;

SHIBASAKI, M .

TETRAHEDRON LETTERS, 1993, 34 (52) :8509-8512

[34]

Oida S, 2000, CHEM PHARM BULL, V48, P694, DOI 10.1248/cpb.48.694

[35]

PIERA J, 2008, ANGEW CHEM, V120, P3558

[36] Catalytic oxidation of organic substrates by molecular oxygen and hydrogen peroxide by multistep electron transfer -: A biomimetic approach [J].

Piera, Julio ;

Backvall, Jan-E. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (19) :3506-3523

[37] Recent advances in transition metal catalyzed oxidation of organic substrates with molecular oxygen [J].

Punniyamurthy, T ;

Velusamy, S ;

Iqbal, J .

CHEMICAL REVIEWS, 2005, 105 (06) :2329-2363

[38] CHEMOSELECTIVE ADDITION OF ORGANOTITANIUM REAGENTS TO CARBONYL-COMPOUNDS [J].

REETZ, MT ;

WESTERMANN, J ;

STEINBACH, R ;

WENDEROTH, B ;

PETER, R ;

OSTAREK, R ;

MAUS, S .

CHEMISCHE BERICHTE-RECUEIL, 1985, 118 (04) :1421-1440

[39]

Riggi I. D., 1988, TETRAHEDRON, V44, P7119

[40] MICROBIOLOGICAL REDUCTION OF KETO-SULFONES - APPLICATION IN A 3-STEP SYNTHESIS OF (S)-(+)-BETA-ANGELICA LACTONE [J].

ROBIN, S ;

HUET, F ;

FAUVE, A ;

VESCHAMBRE, H .

TETRAHEDRON-ASYMMETRY, 1993, 4 (02) :239-246

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