A Concise Synthesis of ortho-Iodobenzyl Alcohols via Addition of ortho-Iodophenyl Grignard Reagent to Aldehydes and Ketones

被引：18

作者：

Cvengros, Jan ^{[1
]}

Stolz, Daniel ^{[1
]}

Togni, Antonio ^{[1
]}

机构：

[1] ETH, Swiss Fed Inst Technol, Dept Chem & Appl Biosci, CH-8093 Zurich, Switzerland

来源：

SYNTHESIS-STUTTGART | 2009年 / 16期

关键词：

addition reactions; Grignard reactions; organometallic reagents; benzyl alcohols; hypervalent iodine compounds; MILD ELECTROPHILIC TRIFLUOROMETHYLATION; AROMATIC-COMPOUNDS; EXCHANGE-REACTION; IODINE; 10-I-3; IODINATION; IODIDES; ARENES; MODEL; ACIDS;

D O I：

10.1055/s-0029-1217406

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A wide range of both secondary and tertiary ortho-iodobenzyl alcohols was synthesized via addition of ortho-iodophenyl Grignard reagents to aldehydes and ketones. Significant improvements in terms of yields were observed with ketones upon addition of CeCl3. The potential application of the target compounds as precursors for novel electrophilic trifluoromethylating reagents based on hypervalent iodine derivatives was demonstrated.

引用

页码：2818 / 2824

页数：7

共 33 条

[1] Direct and waste-free amidations and cycloadditions by organocatalytic activation of carboxylic acids at room temperature [J].

Al-Zoubi, Raed M. ;

Marion, Olivier ;

Hall, Dennis G. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (15) :2876-2879

[2] SYNTHESIS AND REACTION OF SUBSTITUTED ARYLALKOXYIODINANES - FORMATION OF STABLE BROMOARYLALKOXY AND ARYLDIALKOXY HETEROCYCLIC-DERIVATIVES OF TRICOORDINATE ORGANOIODINE(III) [J].

AMEY, RL ;

MARTIN, JC .

JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (11) :1779-1784

[3]

Boymond L, 1998, ANGEW CHEM INT EDIT, V37, P1701, DOI 10.1002/(SICI)1521-3773(19980703)37:12<1701::AID-ANIE1701>3.0.CO

[4]

2-U

[5] Enantioselective synthesis of α,α-disubstituted-α-amino acids by a sequential nucleophilic addition to nitriles [J].

Charette, AB ;

Mellon, C .

TETRAHEDRON, 1998, 54 (35) :10525-10535

[6] Highly enantioselective aryl additions of [AlAr3(thf)] to ketones catalyzed by a Titanium(IV) catalyst of (S)-Binol [J].

Chen, Chien-An ;

Wu, Kuo-Hui ;

Gau, Han-Mou .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (28) :5373-5376

[7] Direct magnesiation of polyfunctionalized arenes and heteroarenes using (tmp)2Mg-2LiCl [J].

Clososki, Giuliano C. ;

Rohbogner, Christoph J. ;

Knochel, Paul .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (40) :7681-7684

[8]

de Meijere A., 2004, METAL CATALYZED CROS

[9] Abstraction of iodine from aromatic iodides by alkyl radicals: Steric and electronic effects [J].

Dolenc, Darko ;

Plesnicar, Bozo .

JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (21) :8028-8036

[10]

Dunne JP, 2003, EUR J INORG CHEM, P458

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