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Literature DB >> 27454146

Benchtop Delivery of Ni(cod)2 using Paraffin Capsules.

Jacob E Dander¹, Nicholas A Weires¹, Neil K Garg¹.

Abstract

A facile method that allows for Ni(cod)2 to be used on the benchtop is reported. The procedure involves the preparation of paraffin-Ni(cod)2 capsules, which are stable to air and moisture. It is demonstrated that these readily available capsules can be used to promote a range of Ni(cod)2-catalyzed transformations. These studies are expected to promote the further use of Ni(cod)2 in organic synthesis.

Entities: Chemical Gene Species

Mesh：

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Year: 2016 PMID： 27454146 PMCID： PMC7010371 DOI： 10.1021/acs.orglett.6b01758

Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.005

22 in total

1. Nickel-catalyzed amination of aryl sulfamates.

Authors: Stephen D Ramgren; Amanda L Silberstein; Yang Yang; Neil K Garg
Journal: Angew Chem Int Ed Engl Date: 2011-01-20 Impact factor: 15.336

2. Ni(COD)2/PCy3 catalyzed cross-coupling of aryl and heteroaryl neopentylglycolboronates with aryl and heteroaryl mesylates and sulfamates in THF at room temperature.

Authors: Pawaret Leowanawat; Na Zhang; Ana-Maria Resmerita; Brad M Rosen; Virgil Percec
Journal: J Org Chem Date: 2011-11-16 Impact factor: 4.354

3. Comparison of arylboron-based nucleophiles in Ni-catalyzed Suzuki-Miyaura cross-coupling with aryl mesylates and sulfamates.

Authors: Na Zhang; David J Hoffman; Nicholas Gutsche; Jayesh Gupta; Virgil Percec
Journal: J Org Chem Date: 2012-06-29 Impact factor: 4.354

4. Nickel-catalyzed chelation-assisted transformations involving ortho C-H bond activation: regioselective oxidative cycloaddition of aromatic amides to alkynes.

Authors: Hirotaka Shiota; Yusuke Ano; Yoshinori Aihara; Yoshiya Fukumoto; Naoto Chatani
Journal: J Am Chem Soc Date: 2011-09-07 Impact factor: 15.419

5. A modular, air-stable nickel precatalyst.

Authors: Jason D Shields; Erin E Gray; Abigail G Doyle
Journal: Org Lett Date: 2015-04-17 Impact factor: 6.005

6. Air-stable nickel precatalysts for fast and quantitative cross-coupling of aryl sulfamates with aryl neopentylglycolboronates at room temperature.

Authors: Ryan L Jezorek; Na Zhang; Pawaret Leowanawat; Matthew H Bunner; Nicholas Gutsche; Aleksander K R Pesti; James T Olsen; Virgil Percec
Journal: Org Lett Date: 2014-12-03 Impact factor: 6.005

7. Palladium-Catalyzed Carbonylative Four-Component Synthesis of Thiochromenones: The Advantages of a Reagent Capsule.

Authors: Chaoren Shen; Anke Spannenberg; Xiao-Feng Wu
Journal: Angew Chem Int Ed Engl Date: 2016-03-17 Impact factor: 15.336

Review 8. Recent advances in homogeneous nickel catalysis.

Authors: Sarah Z Tasker; Eric A Standley; Timothy F Jamison
Journal: Nature Date: 2014-05-15 Impact factor: 49.962

9. Highly reactive, single-component nickel catalyst precursor for Suzuki-Miyuara cross-coupling of heteroaryl boronic acids with heteroaryl halides.

Authors: Shaozhong Ge; John F Hartwig
Journal: Angew Chem Int Ed Engl Date: 2012-11-07 Impact factor: 15.336

Benchtop Delivery of Ni(cod)2 using Paraffin Capsules.

1. Nickel-catalyzed amination of aryl sulfamates.

2. Ni(COD)2/PCy3 catalyzed cross-coupling of aryl and heteroaryl neopentylglycolboronates with aryl and heteroaryl mesylates and sulfamates in THF at room temperature.

3. Comparison of arylboron-based nucleophiles in Ni-catalyzed Suzuki-Miyaura cross-coupling with aryl mesylates and sulfamates.

4. Nickel-catalyzed chelation-assisted transformations involving ortho C-H bond activation: regioselective oxidative cycloaddition of aromatic amides to alkynes.

5. A modular, air-stable nickel precatalyst.

6. Air-stable nickel precatalysts for fast and quantitative cross-coupling of aryl sulfamates with aryl neopentylglycolboronates at room temperature.

7. Palladium-Catalyzed Carbonylative Four-Component Synthesis of Thiochromenones: The Advantages of a Reagent Capsule.

Review 8. Recent advances in homogeneous nickel catalysis.

9. Highly reactive, single-component nickel catalyst precursor for Suzuki-Miyuara cross-coupling of heteroaryl boronic acids with heteroaryl halides.

10. A two-step approach to achieve secondary amide transamidation enabled by nickel catalysis.

1. Activation of C-O and C-N Bonds Using Non-Precious-Metal Catalysis.

2. Breaking Amides using Nickel Catalysis.

3. Well-defined nickel and palladium precatalysts for cross-coupling.

4. Cross-Coupling and Related Reactions: Connecting Past Success to the Development of New Reactions for the Future.

5. Nickel-Catalyzed Reduction of Secondary and Tertiary Amides.

6. Nickel-Catalyzed Esterification of Aliphatic Amides.

7. Nickel-Catalyzed Suzuki-Miyaura Coupling of Aliphatic Amides.

8. Breaking Amide C-N Bonds in an Undergraduate Organic Chemistry Laboratory.

9. Mizoroki-Heck Cyclizations of Amide Derivatives for the Introduction of Quaternary Centers.

10. Ni-Catalyzed Suzuki-Miyaura Cross-Coupling of Aliphatic Amides on the Benchtop.