Regioselective electrophilic borylation of haloarenes

被引：60

作者：

Del Grosso, Alessandro ^{[1
]}

Carrillo, Josue Ayuso ^{[1
]}

Ingleson, Michael J. ^{[1
]}

机构：

[1] Univ Manchester, Sch Chem, Manchester M13 9PL, Lancs, England

来源：

CHEMICAL COMMUNICATIONS | 2015年 / 51卷 / 14期

基金：

欧洲研究理事会; 英国工程与自然科学研究理事会;

关键词：

ARENE BORYLATION; BONDS; CATIONS; STATE;

D O I：

10.1039/c4cc10153g

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Haloarenes undergo direct borylation using amine : BCl3:AlCl3 in the ratio of 1 : 1 : 2. After esterification the pinacol boronate esters are isolated in good yield with regioselectivity controlled by steric and electronic effects.

引用

页码：2878 / 2881

页数：4

共 31 条

[1] Diflunisal analogues stabilize the native state of transthyretin. Potent inhibition of amyloidogenesis [J].

Adamski-Werner, SL ;

Palaninathan, SK ;

Sacchettini, JC ;

Kelly, JW .

JOURNAL OF MEDICINAL CHEMISTRY, 2004, 47 (02) :355-374

[2] Mechanistic Studies into Amine-Mediated Electrophilic Arene Borylation and Its Application in MIDA Boronate Synthesis [J].

Bagutski, Viktor ;

Del Grosso, Alessandro ;

Carrillo, Josue Ayuso ;

Cade, Ian A. ;

Helm, Matthew D. ;

Lawson, James R. ;

Singleton, Paul J. ;

Solomon, Sophia A. ;

Marcelli, Tommaso ;

Ingleson, Michael J. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (01) :474-487

[3] DIRECTIVE EFFECTS IN AROMATIC SUBSTITUTION .30. ELECTROPHILIC SUBSTITUENT CONSTANTS [J].

BROWN, HC ;

OKAMOTO, Y .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1958, 80 (18) :4979-4987

[4]

BUJWID ZJ, 1959, CHEM IND-LONDON, P1091

[5] Remarkably selective iridium catalysts for the elaboration of aromatic C-H bonds [J].

Cho, JY ;

Tse, MK ;

Holmes, D ;

Maleczka, RE ;

Smith, MR .

SCIENCE, 2002, 295 (5553) :305-308

[6] [(acridine)BCl2]+ : A Borenium Cation That Is a Strong Boron- and Carbon-Based Lewis Acid [J].

Clark, Ewan R. ;

Ingleson, Michael J. .

ORGANOMETALLICS, 2013, 32 (22) :6712-6717

[7] Optimization of 1,2,3,4-Tetrahydroacridin-9(10H)-ones as Antimalarials Utilizing Structure-Activity and Structure-Property Relationships [J].

Cross, R. Matthew ;

Maignan, Jordany R. ;

Mutka, Tina S. ;

Luong, Lisa ;

Sargent, Justin ;

Kyle, Dennis E. ;

Manetsch, Roman .

JOURNAL OF MEDICINAL CHEMISTRY, 2011, 54 (13) :4399-4426

[8] Simple inexpensive boron electrophiles for direct arene borylation [J].

Del Grosso, Alessandro ;

Helm, Matthew D. ;

Solomon, Sophia A. ;

Caras-Quintero, Dolores ;

Ingleson, Michael J. .

CHEMICAL COMMUNICATIONS, 2011, 47 (46) :12459-12461

[9] Pinacol Boronates by Direct Arene Borylation with Borenium Cations [J].

Del Grosso, Alessandro ;

Singleton, Paul J. ;

Muryn, Christopher A. ;

Ingleson, Michael J. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (09) :2102-2106

[10] A Pentacoordinate Boron-Containing π-Electron System with CI-B-CI Three-Center Four-Electron Bonds [J].

Dou, Chuandong ;

Saito, Shohei ;

Yamaguchi, Shigehiro .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (25) :9346-9349

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