Efficient Hydrolysis of Organotrifluoroborates via Silica Gel and Water

被引：88

作者：

Molander, Gary A. ^{[1
]}

Cavalcanti, Livia N. ^{[1
]}

Canturk, Belgin ^{[1
]}

Pan, Po-Shen ^{[1
]}

Kennedy, Lauren E. ^{[1
]}

机构：

[1] Univ Penn, Dept Chem, Roy & Diana Vagelos Labs, Philadelphia, PA 19104 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2009年 / 74卷 / 19期

基金：

美国国家卫生研究院;

关键词：

CROSS-COUPLING REACTIONS; BORONIC ACIDS; PROTEASOME; PERSPECTIVES; INHIBITORS; CONVERSION; ESTERS;

D O I：

10.1021/jo901441u

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A general, mild, and efficient method for the hydrolysis of organotrifluoroborates to unveil boronic acids using silica gel and H2O was developed. This method proved to be tolerant of a broad range of aryl-, heteroaryl-, alkenyl-, and alkyltrifluoroborates as well as structurally diverse aminomethylated organotrifluoroborates. As anticipated, electron-rich substrates provided the corresponding boronic acids more readily than electron-poor substrates, owing to the resonance-stabilized difluoroborane intermediate. The method developed was expanded further for the conversion of organotrifluoroborates to the corresponding boronate esters.

引用

页码：7364 / 7369

页数：6

共 32 条

[1] Potential for proteasome inhibition in the treatment of cancer [J].

Adams, J .

DRUG DISCOVERY TODAY, 2003, 8 (07) :307-315

[2] Preclinical and clinical evaluation of proteasome inhibitor PS-341 for the treatment of cancer [J].

Adams, J .

CURRENT OPINION IN CHEMICAL BIOLOGY, 2002, 6 (04) :493-500

[3] Potent and selective inhibitors of the proteasome: Dipeptidyl boronic acids [J].

Adams, J ;

Behnke, M ;

Chen, SW ;

Cruickshank, AA ;

Dick, LR ;

Grenier, L ;

Klunder, JM ;

Ma, YT ;

Plamondon, L ;

Stein, RL .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1998, 8 (04) :333-338

[4] Cavitand boronic acids mediate highly selective fructose transport [J].

Altamore, TM ;

Barrett, ES ;

Duggan, PJ ;

Sherburn, MS ;

Szydzik, ML .

ORGANIC LETTERS, 2002, 4 (20) :3489-3491

[5] Reductive amination with 5-ethyl-2-methylpyridine borane [J].

Burkhardt, Elizabeth R. ;

Coleridge, Brian M. .

TETRAHEDRON LETTERS, 2008, 49 (35) :5152-5155

[6] Probing Intramolecular B-N Interactions in Ortho-Aminomethyl Arylboronic Acids [J].

Collins, Byron E. ;

Sorey, Steven ;

Hargrove, Amanda E. ;

Shabbir, Shagufta H. ;

Lynch, Vincent M. ;

Anslyn, Eric V. .

JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (11) :4055-4060

[7] Potassium trifluoro(organo)borates: New perspectives in organic chemistry [J].

Darses, S ;

Genet, JP .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2003, 2003 (22) :4313-4327

[8] Potassium organotrifluoroborates: New perspectives in organic synthesis [J].

Darses, Sylvain ;

Genet, Jean-Pierre .

CHEMICAL REVIEWS, 2008, 108 (01) :288-325

[9]

Hall D, 2005, BORONIC ACIDS: PREPARATION AND APPLICATIONS IN ORGANIC SYNTHESIS AND MEDICINE, pXV

[10]

KAUFMANN DE, 2005, SCI SYNTHESIS BORON, V6

← 1 2 3 4 →