Oxidation of carbon-silicon bonds: The dramatic advantage of strained siletanes

被引：60

作者：

Sunderhaus, JD ^{[1
]}

Lam, H ^{[1
]}

Dudley, GB ^{[1
]}

机构：

[1] Florida State Univ, Dept Chem & Biochem, Tallahassee, FL 32306 USA

来源：

ORGANIC LETTERS | 2003年 / 5卷 / 24期

关键词：

D O I：

10.1021/ol035695y

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Herein we report on the use of siletanes as substrates for the oxidation of carbon-silicon bonds. These tetraalkylsilanes are easy to handle yet susceptible to rapid ring opening and oxidation upon exposure to aqueous fluoride and peroxide. This combination of stability and reactivity presents many practical benefits, including compatibility with silicon protecting groups and electron-rich aromatic rings.

引用

页码：4571 / 4573

页数：3

共 29 条

[1] The phenylthiocyclopropylsilyl group: a useful latent hydroxy group [J].

Angelaud, R ;

Landais, Y .

TETRAHEDRON, 2000, 56 (14) :2025-2036

[2] SILAETHENES .1. SYNTHESIS AND CHARACTERIZATION OF MONOSILACYCLOBUTANES [J].

AUNER, N ;

GROBE, J .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1980, 188 (01) :25-52

[3] Fleming-Tamao oxidation and masked hydroxyl functionality: Total synthesis of (+)-pramanicin and structural elucidation of the antifungal natural product (-)-pramanicin [J].

Barrett, AGM ;

Head, J ;

Smith, ML ;

Stock, NS ;

White, AJP ;

Williams, DJ .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (16) :6005-6018

[4] Toward a versatile allylation reagent: Practical, enantioselective allylation of acylhydrazones using strained silacycles [J].

Berger, R ;

Rabbat, PMA ;

Leighton, JL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (32) :9596-9597

[5] Design and implementation of new, silicon-based, cross-coupling reactions: Importance of silicon-oxygen bonds [J].

Denmark, SE ;

Sweis, RF .

ACCOUNTS OF CHEMICAL RESEARCH, 2002, 35 (10) :835-846

[6] CHEMISTRY OF ENOXYSILACYCLOBUTANES - HIGHLY SELECTIVE UNCATALYZED ALDOL ADDITIONS [J].

DENMARK, SE ;

GRIEDEL, BD ;

COE, DM ;

SCHNUTE, ME .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (16) :7026-7043

[7] Diastereoselective silacyclopropanations of functionalized chiral alkenes [J].

Driver, TG ;

Franz, AK ;

Woerpel, KA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (23) :6524-6525

[8] STEREOSELECTIVE SAMARIUM(II)-INDUCED COUPLING OF BETA-SILYLACRYLIC ESTERS - A SYNTHESIS OF (+/-)-2-DEOXYRIBONOLACTONE [J].

FLEMING, I ;

GHOSH, SK .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1992, (24) :1775-1777

[9] A ONE-POT CONVERSION OF THE PHENYLDIMETHYLSILYL GROUP INTO A HYDROXYL GROUP [J].

FLEMING, I ;

SANDERSON, PEJ .

TETRAHEDRON LETTERS, 1987, 28 (36) :4229-4232

[10] THE PHENYLDIMETHYLSILYL GROUP AS A MASKED FORM OF THE HYDROXY GROUP [J].

FLEMING, I ;

HENNING, R ;

PLAUT, H .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1984, (01) :29-31

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