Direct introduction of a naphthalene-1,8-diamino boryl [B(dan)] group by a Pd-catalysed selective boryl transfer reaction

被引：71

作者：

Xu, Liang

Li, Pengfei ^{[1
]}

机构：

[1] Xi An Jiao Tong Univ, Ctr Organ Chem, Frontier Inst Sci & Technol, Xian 710054, Shaanxi, Peoples R China

来源：

CHEMICAL COMMUNICATIONS | 2015年 / 51卷 / 26期

基金：

美国国家科学基金会;

关键词：

CROSS-COUPLING REACTION; ALPHA; BETA-UNSATURATED CONJUGATED COMPOUNDS; BORYLALKENES ASYMMETRIC-SYNTHESIS; ALKOXY DIBORON REAGENTS; C-H BORYLATION; BUILDING-BLOCKS; ARYL CHLORIDES; FORMAL HYDROBORATION; EFFICIENT SYNTHESIS; ITERATIVE SYNTHESIS;

D O I：

10.1039/c5cc00231a

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A non-symmetrical diboron reagent, B(pin)-B(dan), has been utilised in the Pd-catalysed borylation of aryl bromides and chlorides. Remarkably selective formation of aryl-B(dan) bonds is established. This represents a direct and efficient way to introduce masked boronic acids. The synthetic usefulness of this reaction is demonstrated in the preparation of boron-differentiated di- and polyboron compounds.

引用

页码：5656 / 5659

页数：4

共 55 条

[1] Palladium-catalyzed borylation of aryl chlorides: Scope, applications, and computational studies [J].

Billingsley, Kelvin L. ;

Barder, Timothy E. ;

Buchwald, Stephen L. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (28) :5359-5363

[2] Efficient Synthesis of Aryl Boronates via Zinc-Catalyzed Cross-Coupling of Alkoxy Diboron Reagents with Aryl Halides at Room Temperature [J].

Bose, Shubhankar Kumar ;

Marder, Todd B. .

ORGANIC LETTERS, 2014, 16 (17) :4562-4565

[3] A Clear- Cut Example of Selective Bpin - Bdan Activation and Precise Bdan Transfer on Boron Conjugate Addition [J].

Cid, Jessica ;

Carbo, Jorge J. ;

Fernandez, Elena .

CHEMISTRY-A EUROPEAN JOURNAL, 2014, 20 (13) :3616-3620

[4] Regio- and Enantioselective Copper(I)-Catalyzed Hydroboration of Borylalkenes: Asymmetric Synthesis of 1,1-Diborylalkanes [J].

Feng, Xinhui ;

Jeon, Heekyung ;

Yun, Jaesook .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (14) :3989-3992

[5] Total Synthesis of Synechoxanthin through Iterative Cross-Coupling [J].

Fujii, Seiko ;

Chang, Stephanie Y. ;

Burke, Martin D. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (34) :7862-7864

[6] Structure and Reactivity of a Preactivated sp2-sp3 Diboron Reagent: Catalytic Regioselective Boration of α,β-Unsaturated Conjugated Compounds [J].

Gao, Ming ;

Thorpe, Steven B. ;

Kleeberg, Christian ;

Slebodnick, Carla ;

Marder, Todd B. ;

Santos, Webster L. .

JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (10) :3997-4007

[7] sp2-sp3 Hybridized Mixed Diboron: Synthesis, Characterization, and Copper-Catalyzed β-Boration of α,β-Unsaturated Conjugated Compounds [J].

Gao, Ming ;

Thorpe, Steven B. ;

Santos, Webster L. .

ORGANIC LETTERS, 2009, 11 (15) :3478-3481

[8] Multistep Synthesis of Complex Boronic Acids from Simple MIDA Boronates [J].

Gillis, Eric P. ;

Burke, Martin D. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (43) :14084-+

[9] A simple and modular strategy for small molecule synthesis: Iterative Suzuki-Miyaura coupling of B-protected haloboronic acid building blocks [J].

Gillis, Eric P. ;

Burke, Martin D. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (21) :6716-+

[10]

Hall DG, 2011, BORONIC ACIDS, VOL 2: PREPARATION AND APPLICATIONS IN ORGANIC SYNTHESIS, MEDICINE AND MATERIALS, 2ND EDITION, P1, DOI 10.1002/9783527639328

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