Iron-Catalyzed Borylation of Alkyl Electrophiles

被引：174

作者：

Atack, Thomas C. ^{[1
]}

Lecker, Rachel M. ^{[1
]}

Cook, Silas P. ^{[1
]}

机构：

[1] Indiana Univ, Dept Chem, Bloomington, IN 47405 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2014年 / 136卷 / 27期

关键词：

CROSS-COUPLING REACTION; HALIDES; PALLADIUM; ARYL; SECONDARY; REAGENTS; ESTERS;

D O I：

10.1021/ja505199u

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The use of low-cost iron(III) acetoacetate (Fe(acac)(3)) and tetramethylethylenediamine (TMEDA) enables the direct cross-coupling of alkyl halides with bis(pinacolato)diboron. This approach allows for the borylation of activated or unactivated primary, secondary, and tertiary bromides. Moreover, even the borylation of benzylic or allylic chlorides, tosylates, and mesylates are possible. The reactions proceed under mild conditions at room temperature and show broad functional-group compatibility and "robustness" as measured by a modified Glorius robustness screen.

引用

收藏

页码：9521 / 9523

页数：3

相关论文

共 22 条

[1] Iron-Catalyzed Cross-Coupling Reactions of Alkyl Grignards with Aryl Sulfamates and Tosylates [J].

Agrawal, Toolika ;

Cook, Silas P. .

ORGANIC LETTERS, 2013, 15 (01) :96-99

[2] Palladium nanoparticle catalysis: borylation of aryl and benzyl halides and one-pot biaryl synthesis via sequential borylation-Suzuki-Miyaura coupling [J].

Bej, Ansuman ;

Srimani, Dipankar ;

Sarkar, Amitabha .

GREEN CHEMISTRY, 2012, 14 (03) :661-667

[3] Zinc-Catalyzed Borylation of Primary, Secondary and Tertiary Alkyl Halides with Alkoxy Diboron Reagents at Room Temperature [J].

Bose, Shubhankar Kumar ;

Fucke, Katharina ;

Liu, Lei ;

Steel, Patrick G. ;

Marder, Todd B. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (07) :1799-1803

[4]

Brown H.C., 1962, HYDROBORATION

[5] ORGANOBORANES .31. A SIMPLE PREPARATION OF BORONIC ESTERS FROM ORGANO-LITHIUM REAGENTS AND SELECTED TRIALKOXYBORANES [J].

BROWN, HC ;

COLE, TE .

ORGANOMETALLICS, 1983, 2 (10) :1316-1319

[6] On the Role of Metal Contaminants in Catalyses with FeCl3 [J].

Buchwald, Stephen L. ;

Bolm, Carsten .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (31) :5586-5587

[7] Hydride as a Leaving Group in the Reaction of Pinacolborane with Halides under Ambient Grignard and Barbier Conditions. One-Pot Synthesis of Alkyl, Aryl, Heteroaryl, Vinyl, and Allyl Pinacolboronic Esters [J].

Clary, Jacob W. ;

Rettenmaier, Terry J. ;

Snelling, Rachel ;

Bryks, Whitney ;

Banwell, Jesse ;

Wipke, W. Todd ;

Singaram, Bakthan .

JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (23) :9602-9610

[8]

Collins KD, 2013, NAT CHEM, V5, P597, DOI [10.1038/nchem.1669, 10.1038/NCHEM.1669]

[9] Nickel-Catalyzed Coupling Reactions of Alkyl Electrophiles, Including Unactivated Tertiary Halides, To Generate Carbon-Boron Bonds [J].

Dudnik, Alexander S. ;

Fu, Gregory C. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (25) :10693-10697

[10]

Fu G.C., 2008, Transition Metals for Organic Synthesis, P193