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Literature DB >> 16381568

Vinylation of aryl bromides using an inexpensive vinylpolysiloxane.

Abstract

[reaction: see text] A mild and general method for the palladium-catalyzed vinylation of aryl bromides has been developed. The use of tetrabutylammonium fluoride (TBAF) as the activator and an inexpensive and nontoxic vinyl donor, 1,3,5,7-tetramethyl-1,3,5,7-tetravinylcyclotetrasiloxane (D(4)(V), 1), allows for a general and high-yielding preparation of substituted styrenes.

Entities: Chemical Species

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Year: 2006 PMID： 16381568 DOI： 10.1021/ol052517r

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

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Cited

12 in total

1. Low Pressure Vinylation of Aryl and Vinyl Halides via Heck-Mizoroki Reactions Using Ethylene.

Authors: Craig R Smith; T V Rajanbabu
Journal: Tetrahedron Date: 2010-01-30 Impact factor: 2.457

2. Enantioselective Synthesis of 4-Methyl-3,4-dihydroisocoumarin via Asymmetric Hydroformylation of Styrene Derivatives.

Authors: Bo Qu; Renchang Tan; Madison R Herling; Nizar Haddad; Nelu Grinberg; Marisa C Kozlowski; Xumu Zhang; Chris H Senanayake
Journal: J Org Chem Date: 2019-03-06 Impact factor: 4.354

3. Studies of microwave-enhanced Suzuki-Miyaura vinylation of electron-rich sterically hindered substrates utilizing potassium vinyltrifluoroborate.

Authors: Matthew D Brooker; Stefan M Cooper; Dena R Hodges; Rhiannon R Carter; Justin K Wyatt
Journal: Tetrahedron Lett Date: 2010-12-22 Impact factor: 2.415

4. Suzuki-Miyaura cross-coupling reactions of potassium vinyltrifluoroborate with aryl and heteroaryl electrophiles.

Authors: Gary A Molander; Adam R Brown
Journal: J Org Chem Date: 2006-12-22 Impact factor: 4.354

5. Development of Chiral Bis-hydrazone Ligands for the Enantioselective Cross-Coupling Reactions of Aryldimethylsilanolates.

Authors: Scott E Denmark; Wen-Tau T Chang; K N Houk; Peng Liu
Journal: J Org Chem Date: 2014-12-10 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

Vinylation of aryl bromides using an inexpensive vinylpolysiloxane.

1. Low Pressure Vinylation of Aryl and Vinyl Halides via Heck-Mizoroki Reactions Using Ethylene.

2. Enantioselective Synthesis of 4-Methyl-3,4-dihydroisocoumarin via Asymmetric Hydroformylation of Styrene Derivatives.

3. Studies of microwave-enhanced Suzuki-Miyaura vinylation of electron-rich sterically hindered substrates utilizing potassium vinyltrifluoroborate.

4. Suzuki-Miyaura cross-coupling reactions of potassium vinyltrifluoroborate with aryl and heteroaryl electrophiles.

5. Development of Chiral Bis-hydrazone Ligands for the Enantioselective Cross-Coupling Reactions of Aryldimethylsilanolates.

Review 6. Biaryl phosphane ligands in palladium-catalyzed amination.

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

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

9. Vinyl Tris(trimethylsilyl)silanes: Substrates for Hiyama Coupling.

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