Oxidative Hydroxylation Mediated by Alkoxysulfonium Ions

被引：78

作者：

Ashikari, Yosuke ^{[1
]}

Nokami, Toshiki ^{[1
]}

Yoshida, Jun-ichi ^{[1
]}

机构：

[1] Kyoto Univ, Grad Sch Engn, Dept Synthet Chem & Biol Chem, Nishikyou Ku, Kyoto 6158510, Japan

来源：

ORGANIC LETTERS | 2012年 / 14卷 / 03期

关键词：

CATION-POOL METHOD; OLEFIN COUPLING REACTIONS; CIS-DIHYDROXYLATION; ORGANIC-SYNTHESIS; ANODIC-OXIDATION; TANDEM CATALYSIS; GENERATION; POT; CARBON; ACID;

D O I：

10.1021/ol203467v

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Oxidative hydroxylation of toluene derivatives via alkoxysulfonium ion intermediates was achieved by integration of anodic oxidation and hydrolysis to give benzyl alcohols which are also susceptible to oxidation. Alkenes were also oxidized to give 1,2-diols without overoxidation. The integration of electrochemical oxidative cyclization and hydrolysis was achieved using alkenes bearing a nitrogen atom in an appropriate position to give cyclic beta-amino-substituted alcohols.

引用

页码：938 / 941

页数：4

共 92 条

[1]

Adam W., 2000, PEROXIDE CHEM MECH P

[2] Integrated Electrochemical-Chemical Oxidation Mediated by Alkoxysulfonium Ions [J].

Ashikari, Yosuke ;

Nokami, Toshiki ;

Yoshida, Jun-ichi .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (31) :11840-11843

[3] Facile Carbolithiation of Bent Alkyne without Catalyst. Tandem Route to Dibenzo[b,f]pentalenes from Dibenzocyclooctadiyne [J].

Babu, Govindarajulu ;

Orita, Akihiro ;

Otera, Junzo .

CHEMISTRY LETTERS, 2008, 37 (12) :1296-1297

[4] Multicomponent reactions to form heterocycles by microwave-assisted continuous flow organic synthesis [J].

Bremner, W. Stacy ;

Organ, Michael G. .

JOURNAL OF COMBINATORIAL CHEMISTRY, 2007, 9 (01) :14-16

[5] Multicatalytic Synthesis of α-Pyrrolidinyl Ketones via a Tandem Palladium(II)/Indium(III)-Catalyzed Aminochlorocarbonylation/Friedel-Crafts Acylation Reaction [J].

Cernak, Tim A. ;

Lambert, Tristan H. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (09) :3124-+

[6] Combining pot, atom and step economy (PASE) in organic synthesis. Synthesis of tetrahydropyran-4-ones [J].

Clarke, Paul A. ;

Santos, Soraia ;

Martin, William H. C. .

GREEN CHEMISTRY, 2007, 9 (05) :438-440

[7] Manganese catalysed asymmetric cis-dihydroxylation with H2O2 [J].

de Boer, Johannes W. ;

Browne, Wesley R. ;

Harutyunyan, Syuzanna R. ;

Bini, Laura ;

Tiemersma-Wegman, Theodora D. ;

Alsters, Paul L. ;

Hage, Ronald ;

Feringa, Ben L. .

CHEMICAL COMMUNICATIONS, 2008, (32) :3747-3749

[8] cis-Dihydroxylation and epoxidation of alkenes by [Mn2O(RCO2)2(tmtacn)2]:: Tailoring the selectivity of a highly H2O2-efficient catalyst [J].

de Boer, JW ;

Brinksma, J ;

Browne, WR ;

Meetsma, A ;

Alsters, PL ;

Hage, R ;

Feringa, BL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (22) :7990-7991

[9] The virtue of palladium-catalyzed domino reactions -: Diverse oligocyclizations of acyclic 2-bromoenynes and 2-bromoenediynes [J].

De Meijere, A ;

Von Zezschwitz, P ;

Bräse, S .

ACCOUNTS OF CHEMICAL RESEARCH, 2005, 38 (05) :413-422

[10] Dihydroxylation of olefins using air as the terminal oxidant [J].

Döbler, C ;

Mehltretter, GM ;

Sundermeier, U ;

Beller, M .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2001, 621 (1-2) :70-76

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