Functional Group Interconversion: Decarbonylative Borylation of Esters for the Synthesis of Organoboronates

被引：79

作者：

Guo, Lin ^{[1
]}

Rueping, Magnus ^{[1
,2
]}

机构：

[1] Rhein Westfal TH Aachen, Inst Organ Chem, Landoltweg 1, D-52074 Aachen, Germany

[2] King Abdullah Univ Sci & Technol KAUST, KAUST Catalysis Ctr KCC, Thuwal 239556900, Saudi Arabia

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2016年 / 22卷 / 47期

关键词：

C-H borylation; C-O bond activation; decarbonylative cross-coupling; esters; nickel; CROSS-COUPLING REACTIONS; METAL-FREE BORYLATION; MIXED-LIGAND SYSTEMS; CATALYZED BORYLATION; BOND ACTIVATION; ARYL HALIDES; O BOND; ROOM-TEMPERATURE; NICKEL CATALYSIS; BORONIC ACID;

D O I：

10.1002/chem.201604504

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A new and efficient nickel-catalyzed decarbonylative borylation reaction of carboxylic acid esters with bis(pinacolato)-diboron has been developed. This transformation allows access to structurally diverse aryl as well as alkenyl and alkyl boronate esters with high reactivity, broad substrate scope, and excellent functional-group tolerance. Further experiments show that this protocol can be carried out on a gram scale and applied to orthogonal synthetic strategies.

引用

页码：16786 / 16789

页数：4

共 67 条

[11] Carboxylates as sources of carbon nucleophiles and electrophiles: comparison of decarboxylative and decarbonylative pathways [J].

Dzik, Wojciech I. ;

Lange, Paul P. ;

Goossen, Lukas J. .

CHEMICAL SCIENCE, 2012, 3 (09) :2671-2678

[12] Decarbonylative heck olefination of enol esters: Salt-free and environmentally friendly access to vinyl arenes [J].

Goossen, LJ ;

Paetzold, J .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (09) :1095-1098

[13]

Goossen LJ, 2002, ANGEW CHEM INT EDIT, V41, P1237, DOI 10.1002/1521-3773(20020402)41:7<1237::AID-ANIE1237>3.0.CO

[14]

2-F

[15] Ruthenium catalyzed decarbonylative arylation at Sp3 carbon centers in pyrrolidine and piperidine heterocycles [J].

Gribkov, Denis V. ;

Pastine, Stefan J. ;

Schnuerch, Michael ;

Sames, Dalibor .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (38) :11750-11755

[16]

Guo L., 2016, ANGEW CHEM, V128, P11989

[17] Decarbonylative Silylation of Esters by Combined Nickel and Copper Catalysis for the Synthesis of Arylsilanes and Heteroarylsilanes [J].

Guo, Lin ;

Chatupheeraphat, Adisak ;

Rueping, Magnus .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (39) :11810-11813

[18] Nickel-Catalyzed Csp2-Csp3 Cross-Coupling via C-O Bond Activation [J].

Guo, Lin ;

Hsiao, Chien-Chi ;

Yue, Huifeng ;

Liu, Xiangqian ;

Rueping, Magnus .

ACS CATALYSIS, 2016, 6 (07) :4438-4442

[19] Nickel catalyzed dealkoxylative Csp2-Csp3 cross coupling reactions - stereospecific synthesis of allylsilanes from enol ethers [J].

Guo, Lin ;

Leiendecker, Matthias ;

Hsiao, Chien-Chi ;

Baumann, Christoph ;

Rueping, Magnus .

CHEMICAL COMMUNICATIONS, 2015, 51 (10) :1937-1940

[20]

Hall DG, 2005, BORONIC ACIDS: PREPARATION AND APPLICATIONS IN ORGANIC SYNTHESIS AND MEDICINE, P1, DOI 10.1002/3527606548

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