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Literature DB >> 19081992

Palladium- (and nickel-) catalyzed vinylation of aryl halides.

Abstract

Functionalized styrenes are extremely useful building blocks for organic synthesis and for functional polymers. One of the most general syntheses of styrenes involves the combination of an aryl halide with a vinyl organometallic reagent under catalysis by palladium or nickel complexes. This Feature Article provides the first comprehensive summary of the vinylation methods currently available along with a critical comparison of the efficiency, cost and scope of the methods.

Entities: Chemical Disease Gene Species

Year: 2008 PMID： 19081992 PMCID： PMC2716051 DOI： 10.1039/b809676g

Source DB: PubMed Journal: Chem Commun (Camb) ISSN： 1359-7345 Impact factor: 6.222

22 in total

Review 1. Design and implementation of new, silicon-based, cross-coupling reactions: importance of silicon-oxygen bonds.

Authors: Scott E Denmark; Ramzi F Sweis
Journal: Acc Chem Res Date: 2002-10 Impact factor: 22.384

2. Removal, recovery, and recycling of triarylphosphonium-supported tin reagents for various organic transformations.

Authors: Jean-Christophe Poupon; David Marcoux; Jean-Manuel Cloarec; André B Charette
Journal: Org Lett Date: 2007-08-02 Impact factor: 6.005

3. The First General Method for Stille Cross-Couplings of Aryl Chlorides.

Authors:
Journal: Angew Chem Int Ed Engl Date: 1999-08 Impact factor: 15.336

4. Catalysts for Suzuki-Miyaura coupling processes: scope and studies of the effect of ligand structure.

Authors: Timothy E Barder; Shawn D Walker; Joseph R Martinelli; Stephen L Buchwald
Journal: J Am Chem Soc Date: 2005-04-06 Impact factor: 15.419

5. Pd/P(t-Bu)(3): a mild and general catalyst for Stille reactions of aryl chlorides and aryl bromides.

Authors: Adam F Littke; Lothar Schwarz; Gregory C Fu
Journal: J Am Chem Soc Date: 2002-06-05 Impact factor: 15.419

6. Efficient cross-coupling reactions of aryl chlorides and bromides with phenyl- or vinyltrimethoxysilane mediated by a Palladium/Imidazolium chloride system

Authors:
Journal: Org Lett Date: 2000-07-13 Impact factor: 6.005

7. Palladium/imidazolium salt catalyzed coupling of aryl halides with hypervalent organostannates.

Authors: G A Grasa; S P Nolan
Journal: Org Lett Date: 2001-01-11 Impact factor: 6.005

8. Aqueous sodium hydroxide promoted cross-coupling reactions of alkenyltrialkoxysilanes under ligand-free conditions.

Authors: Emilio Alacid; Carmen Najera
Journal: J Org Chem Date: 2008-02-20 Impact factor: 4.354

9. Generation of substituted styrenes via Suzuki cross-coupling of aryl halides with 2,4,6-trivinylcyclotriboroxane.

Authors: Fergal Kerins; Donal F O'Shea
Journal: J Org Chem Date: 2002-07-12 Impact factor: 4.354

10. Vinylation of aromatic halides using inexpensive organosilicon reagents. Illustration of design of experiment protocols.

Authors: Scott E Denmark; Christopher R Butler
Journal: J Am Chem Soc Date: 2008-02-28 Impact factor: 15.419

14 in total

Palladium- (and nickel-) catalyzed vinylation of aryl halides.

Review 1. Design and implementation of new, silicon-based, cross-coupling reactions: importance of silicon-oxygen bonds.

2. Removal, recovery, and recycling of triarylphosphonium-supported tin reagents for various organic transformations.

3. The First General Method for Stille Cross-Couplings of Aryl Chlorides.

4. Catalysts for Suzuki-Miyaura coupling processes: scope and studies of the effect of ligand structure.

5. Pd/P(t-Bu)(3): a mild and general catalyst for Stille reactions of aryl chlorides and aryl bromides.

6. Efficient cross-coupling reactions of aryl chlorides and bromides with phenyl- or vinyltrimethoxysilane mediated by a Palladium/Imidazolium chloride system

7. Palladium/imidazolium salt catalyzed coupling of aryl halides with hypervalent organostannates.

8. Aqueous sodium hydroxide promoted cross-coupling reactions of alkenyltrialkoxysilanes under ligand-free conditions.

9. Generation of substituted styrenes via Suzuki cross-coupling of aryl halides with 2,4,6-trivinylcyclotriboroxane.

10. Vinylation of aromatic halides using inexpensive organosilicon reagents. Illustration of design of experiment protocols.

Review 1. Nickel-catalyzed cross-couplings involving carbon-oxygen bonds.

2. Palladium-Catalyzed Selective α-Alkenylation of Pyridylmethyl Ethers with Vinyl Bromides.

3. Silver-mediated fluorination of aryl silanes.

4. Enantioselective alkenylation via nickel-catalyzed cross-coupling with organozirconium reagents.

5. The interplay of invention, discovery, development, and application in organic synthetic methodology: a case study.

6. A general solution for unstable boronic acids: slow-release cross-coupling from air-stable MIDA boronates.

7. Gold-catalyzed oxidative coupling reactions with aryltrimethylsilanes.

8. Dealkenylative Alkenylation: Formal σ-Bond Metathesis of Olefins.

9. Alkenylation of C(sp³ )-H Bonds by Zincation/Copper-Catalyzed Cross-Coupling with Iodonium Salts.

10. Cross-coupling reactions of aromatic and heteroaromatic silanolates with aromatic and heteroaromatic halides.