Electrophilic ipso-iodination of silylated arylboronic acids

被引：12

作者：

Durka, K. ^{[1
]}

Gorka, J. ^{[1
]}

Kurach, P. ^{[1
]}

Lulinski, S. ^{[1
]}

Serwatowski, J. ^{[1
]}

机构：

[1] Warsaw Univ Technol, Fac Chem, Dept Phys Chem, PL-00664 Warsaw, Poland

来源：

JOURNAL OF ORGANOMETALLIC CHEMISTRY | 2010年 / 695卷 / 24期

关键词：

Arylboronic acids; Arylborinic compounds; Arylsilanes; Iodination; Electrophilic ipso-substitution; Suzuki cross-coupling; BONDS;

D O I：

10.1016/j.jorganchem.2010.08.016

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Silylated functionalized arylboronic acids were converted into corresponding iodinated arylboronic acids in good yields via the electrophilic ipso-desilylation effected with iodine chloride in refluxing CHCl3. Disilylated arylboronic acids were susceptible to diiodination. In addition, the structural characterization and reactivity of a novel sterically hindered ortho-silylated diarylborinic ester were reported. The potential of selected iodinated phenylboronic acids as monomers for the SuzukieMiyaura cross-coupling polymerization was demonstrated. (C) 2010 Elsevier B.V. All rights reserved.

引用

页码：2635 / 2643

页数：9

共 32 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] BARRIERS TO ROTATION ABOUT THE B-X BONDS OF COORDINATIVELY UNSATURATED BORATES AND THIOBORATES R2BXR' (X =O, S) ARE NOT MEASURES OF THE RELATIVE STRENGTHS OF THEIR B=O AND B=S PI BONDS [J].

ASHBY, MT ;

SHESHTAWY, NA .

ORGANOMETALLICS, 1994, 13 (01) :236-243

[3] ATOMS IN MOLECULES [J].

BADER, RFW .

ACCOUNTS OF CHEMICAL RESEARCH, 1985, 18 (01) :9-15

[4] Preparation and selective reactions of mixed bimetallic aromatic and heteroaromatic boron-magnesium reagents [J].

Baron, O ;

Knochel, P .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (20) :3133-3135

[5] DENSITY-FUNCTIONAL THERMOCHEMISTRY .3. THE ROLE OF EXACT EXCHANGE [J].

BECKE, AD .

JOURNAL OF CHEMICAL PHYSICS, 1993, 98 (07) :5648-5652

[6]

Biegler-König F, 2001, J COMPUT CHEM, V22, P545, DOI 10.1002/1096-987X(20010415)22:5<545::AID-JCC1027>3.0.CO

[7]

2-Y

[8]

*BRUK AXS, 2008, APEX2 BRUK AXS SAINT

[9] Synthesis, structure, and reactivity of borate ester coordinated organobismuth compounds [J].

Caires, Christopher C. ;

Guccione, Samira .

ORGANOMETALLICS, 2008, 27 (04) :747-752

[10] REGIOSPECIFIC SYNTHESIS OF AROMATIC-COMPOUNDS VIA ORGANOMETALLIC INTERMEDIATES .2. 1,3,5-(TRIMETHYLMETAL(IV))BENZENE COMPOUNDS [J].

CHEN, GJ ;

TAMBORSKI, C .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1983, 251 (02) :149-158

← 1 2 3 4 →