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Literature DB >> 18576604

An improved system for the palladium-catalyzed borylation of aryl halides with pinacol borane.

Kelvin L Billingsley¹, Stephen L Buchwald.

Abstract

A highly efficient method for the palladium-catalyzed borylation of aryl halides with an inexpensive and atom-economical boron source, pinacol borane, has been developed. This system allows for the conversion of aryl and heteroaryl iodides, bromides, and several chlorides, containing a variety of functional groups, to the corresponding pinacol boronate esters. In addition to the increase in substrate scope, this is the first general method where relatively low quantities of catalyst and short reaction times can be employed.

Entities: Chemical

Mesh：

Substances：
Boranes
Palladium
Boron

Year: 2008 PMID： 18576604 PMCID： PMC2574621 DOI： 10.1021/jo800727s

Source DB: PubMed Journal: J Org Chem ISSN： 0022-3263 Impact factor: 4.354

7 in total

1. Palladium-catalyzed borylation of aryl chlorides: scope, applications, and computational studies.

Authors: Kelvin L Billingsley; Timothy E Barder; Stephen L Buchwald
Journal: Angew Chem Int Ed Engl Date: 2007 Impact factor: 15.336

2. Microwave-assisted synthesis of pinacol boronates from aryl chlorides catalyzed by a palladium/imidazolium salt system.

Authors: Alois Fürstner; Günter Seidel
Journal: Org Lett Date: 2002-02-21 Impact factor: 6.005

Review 3. Palladium-catalyzed coupling reactions of aryl chlorides.

Authors: Adam F Littke; Gregory C Fu
Journal: Angew Chem Int Ed Engl Date: 2002-11-15 Impact factor: 15.336

4. Palladium-catalyzed borylation of ortho-substituted phenyl halides and application to the one-pot synthesis of 2,2'-disubstituted biphenyls.

Authors: O Baudoin; D Guénard; F Guéritte
Journal: J Org Chem Date: 2000-12-29 Impact factor: 4.354

5. Palladium-catalyzed borylation of aryl halides or triflates with dialkoxyborane: A novel and facile synthetic route to arylboronates

Authors:
Journal: J Org Chem Date: 2000-01-14 Impact factor: 4.354

6. Metal-catalyzed reactions of diborons for synthesis of organoboron compounds.

Authors: Tatsuo Ishiyama; Norio Miyaura
Journal: Chem Rec Date: 2004 Impact factor: 6.771

7. Palladium-catalyzed borylation of phenyl bromides and application in one-pot Suzuki-Miyaura biphenyl synthesis.

Authors: Pierre-Emmanuel Broutin; Igor Cerna; Maria Campaniello; Frédéric Leroux; Françoise Colobert
Journal: Org Lett Date: 2004-11-25 Impact factor: 6.005

7 in total

22 in total

1. Concise Total Synthesis of (+)-Asperazine, (+)-Pestalazine A, and (+)-iso-Pestalazine A. Structure Revision of (+)-Pestalazine A.

Authors: Richard P Loach; Owen S Fenton; Mohammad Movassaghi
Journal: J Am Chem Soc Date: 2016-01-19 Impact factor: 15.419

2. Boronic acid-containing CXCR1/2 antagonists: Optimization of metabolic stability, in vivo evaluation, and a proposed receptor binding model.

Authors: Dean Y Maeda; Angela M Peck; Aaron D Schuler; Mark T Quinn; Liliya N Kirpotina; Winston N Wicomb; Richard L Auten; Rambabu Gundla; John A Zebala
Journal: Bioorg Med Chem Lett Date: 2015-04-23 Impact factor: 2.823

3. A General and Practical Palladium-Catalyzed Direct α-Arylation of Amides with Aryl Halides.

Authors: Bing Zheng; Tiezheng Jia; Patrick J Walsh
Journal: Adv Synth Catal Date: 2014-01-13 Impact factor: 5.837

4. Differential Dihydrofunctionalization of Terminal Alkynes: Synthesis of Benzylic Alkyl Boronates through Reductive Three-Component Coupling.

Authors: Megan K Armstrong; Gojko Lalic
Journal: J Am Chem Soc Date: 2019-04-03 Impact factor: 15.419

An improved system for the palladium-catalyzed borylation of aryl halides with pinacol borane.

1. Palladium-catalyzed borylation of aryl chlorides: scope, applications, and computational studies.

2. Microwave-assisted synthesis of pinacol boronates from aryl chlorides catalyzed by a palladium/imidazolium salt system.

Review 3. Palladium-catalyzed coupling reactions of aryl chlorides.

4. Palladium-catalyzed borylation of ortho-substituted phenyl halides and application to the one-pot synthesis of 2,2'-disubstituted biphenyls.

5. Palladium-catalyzed borylation of aryl halides or triflates with dialkoxyborane: A novel and facile synthetic route to arylboronates

6. Metal-catalyzed reactions of diborons for synthesis of organoboron compounds.

7. Palladium-catalyzed borylation of phenyl bromides and application in one-pot Suzuki-Miyaura biphenyl synthesis.

1. Concise Total Synthesis of (+)-Asperazine, (+)-Pestalazine A, and (+)-iso-Pestalazine A. Structure Revision of (+)-Pestalazine A.

2. Boronic acid-containing CXCR1/2 antagonists: Optimization of metabolic stability, in vivo evaluation, and a proposed receptor binding model.

3. A General and Practical Palladium-Catalyzed Direct α-Arylation of Amides with Aryl Halides.

4. Differential Dihydrofunctionalization of Terminal Alkynes: Synthesis of Benzylic Alkyl Boronates through Reductive Three-Component Coupling.

5. Practical radical cyclizations with arylboronic acids and trifluoroborates.

6. Enantioselective total synthesis of (+)-lithospermic acid.

7. A versatile catalyst system for Suzuki-Miyaura cross-coupling reactions of C(sp(2))-tosylates and mesylates.

8. Ligand-Promoted Borylation of C(sp(3))-H Bonds with Palladium(II) Catalysts.

9. Nickel-catalyzed borylation of halides and pseudohalides with tetrahydroxydiboron [B2(OH)4].

10. Kinetically controlled E-selective catalytic olefin metathesis.