Hydroboration of Alkenes and Alkynes Employing Earth-Abundant Metal Catalysts

被引：27

作者：

Singh, Arpita ^{[1
]}

Shafiei-Haghighi, Sara ^{[1
]}

Smith, Cecilia R. ^{[1
]}

Unruh, Daniel K. ^{[1
]}

Findlater, Michael ^{[1
]}

机构：

[1] Texas Tech Univ, Dept Chem & Biochem, Lubbock, TX 79409 USA

来源：

ASIAN JOURNAL OF ORGANIC CHEMISTRY | 2020年 / 9卷 / 03期

基金：

美国国家科学基金会;

关键词：

Hydroboration; Alkynes; Alkenes; Iron; BIAN; ELECTRONIC-STRUCTURE; IRON; COMPLEXES; PALLADIUM; LIGANDS; HYDROSILYLATION; 9-BORABICYCLO<3.3.1>NONANE; POLYMERIZATION; BORYLATION;

D O I：

10.1002/ajoc.201900615

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Iron complexes [BIAN]Fe(I)(eta(6)-toluene) (M1) and [BIAN]FeCl2 (M2) (BIAN=bis(2,6-diisopropylaniline)acenaphthene) were found to be viable catalysts for the regioselective hydroboration of alkynes and alkenes. The hydroboration of alkynes and alkenes in the presence of HBpin and an activator at 70 degrees C afforded linear vinyl and alkyl boronic esters, respectively. Selectivity up to 98% was observed for alkyl boronic esters and exclusive formation of trans product was observed for vinyl boronic esters.

引用

页码：416 / 420

页数：5

共 55 条

[1] Low-valent α-diimine iron complexes for catalytic olefin hydrogenation [J].

Bart, SC ;

Hawrelak, EJ ;

Lobkovsky, E ;

Chirik, PJ .

ORGANOMETALLICS, 2005, 24 (23) :5518-5527

[2] Electronic structure of bis(imino)pyridine iron dichloride, monochloride, and neutral ligand complexes: A combined structural, spectroscopic, and computational study [J].

Bart, Suzanne C. ;

Chlopek, Krzysztof ;

Bill, Eckhard ;

Bouwkamp, Marco W. ;

Lobkovsky, Emil ;

Neese, Frank ;

Wieghardt, Karl ;

Chirik, Paul J. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (42) :13901-13912

[3]

Bismuto A., 2016, Angew. Chem., V128, P15582

[4] Aluminum-Catalyzed Hydroboration of Alkenes [J].

Bismuto, Alessandro ;

Cowley, Michael J. ;

Thomas, Stephen P. .

ACS CATALYSIS, 2018, 8 (03) :2001-2005

[5] Aluminum Hydride Catalyzed Hydroboration of Alkynes [J].

Bismuto, Alessandro ;

Thomas, Stephen P. ;

Cowley, Michael J. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (49) :15356-15359

[6] A new iron age [J].

Bolm, Carsten .

NATURE CHEMISTRY, 2009, 1 (05) :420-420

[7] 9-borabicyclo[3.3.1]nonane (9-BBN) in organic synthesis [J].

Bracher, F ;

Litz, T .

JOURNAL FUR PRAKTISCHE CHEMIE-CHEMIKER-ZEITUNG, 1996, 338 (04) :386-389

[8] HYDROBORATION .57. HYDROBORATION WITH 9-BORABICYCLO[3.3.1]NONANE OF ALKENES CONTAINING REPRESENTATIVE FUNCTIONAL-GROUPS [J].

BROWN, HC ;

CHEN, JC .

JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (20) :3978-3988

[9] HYDROBORATION .1. THE REACTION OF OLEFINS WITH SODIUM BOROHYDRIDE ALUMINUM CHLORIDE - A CONVENIENT ROUTE TO ORGANOBORANES AND THE ANTI-MARKOWNIKOFF HYDRATION OF OLEFINS [J].

BROWN, HC ;

RAO, BCS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1959, 81 (24) :6423-6428

[10] BIAN-Fe(η6-C6H6): Synthesis, Characterization, and L-Lactide Polymerization [J].

Brown, Lauren A. ;

Wekesa, Francis S. ;

Unruh, Daniel K. ;

Findlater, Michael ;

Long, Brian K. .

JOURNAL OF POLYMER SCIENCE PART A-POLYMER CHEMISTRY, 2017, 55 (17) :2824-2830

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