Palladium catalysed aryl enol ether synthesis from vinyl triflatesElectronic supplementary information (ESI) available: experimental. See http://www.rsc.org/suppdata/cc/b3/b307574e/

Willis, Michael C.; Taylor, Dawn; Gillmore, Adam T.

doi:10.1039/b307574e

Cited by 39 publications

(20 citation statements)

References 15 publications

(8 reference statements)

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Likewise, it has been demonstrated that rhodium can effectively catalyze the Bamford‐Stevens reaction to access vinyl ethers starting from Eschenmoser hydrazone (Figure B) . However, most of the methods rely on the use of expensive palladium and rhodium catalysts which is not cost effective for the large scale industrial applications –,. On the other hand less expensive metals such as copper, nickel require supporting ligands for the transformation –.…”

Section: Figurementioning

confidence: 99%

A One Pot Transition‐Metal‐Free Synthesis of Styrenyl Ethers from 2‐Aryloxy/Alkoxy Acetophenones

2018

View full text Add to dashboard Cite

A one‐pot transition‐metal‐free synthesis of styrenyl ethers starting from 2‐aryloxy/alkoxy acetophenones is described. The protocol explores the use of tosyl hydrazide and potassium carbonate as a mild base via Bamford‐Stevens reaction to synthesize the styrenyl ethers. The protocol is very simple, practical and uses mild reaction conditions with simple reaction set‐up. This practical protocol proved to be scalable on gram quantity.

show abstract

Section: Figurementioning

confidence: 99%

A One Pot Transition‐Metal‐Free Synthesis of Styrenyl Ethers from 2‐Aryloxy/Alkoxy Acetophenones

2018

View full text Add to dashboard Cite

show abstract

“…17,65 In contrast, there are efficient couplings that employ phenols as the nucleophilic partner to effect vinylation, as demonstrated by Gillmore, Taylor and Willis (Scheme 56). 66 Formation of aryl vinyl ethers via palladium catalysis is a mild method compatible with many functional groups; however, there are a limited number of reports. The related Buchwald-Hartwig coupling 67 to make diaryl ethers is much more common.…”

Section: Palladium-mediated Reactionsmentioning

confidence: 99%

Methods for Vinyl Ether Synthesis

Winternheimer¹,

Shade²,

Merlic³

2010

Synthesis

View full text Add to dashboard Cite

Deceptively simple as the structure may appear, there is no single general method by which to synthesize the vinyl (enol) ether functionality. However, there exists a diverse array of complementary methods by which this functionality has been achieved. This review presents the scope and limitations of these methods according to reaction type, specifically via ether modifications, elimination reactions, carbonyl olefinations, alcohol additions and carbon-oxygen coupling reactions.

show abstract

“…A general and efficient method for the synthesis of N‐ (1‐alkenyl)monoazoles involves palladium‐catalyzed vinylation by vinyl bromides to yield a wide range of target products under mild conditions (50–100 °C) 23. Palladium‐based catalysts can also promote the cross‐coupling of a wide range of phenols with vinyl triflates: alkenyl aryl ethers are thus obtained in good yields at 100 °C 24. Nevertheless, the use of expensive palladium limits the attractiveness of these methods for industrial applications.…”

Section: Introductionmentioning

confidence: 99%

Mild Copper‐Catalyzed Vinylation Reactions of Azoles and Phenols with Vinyl Bromides

Taillefer¹,

Ouali²,

Renard³

et al. 2006

Chemistry A European J

122

View full text Add to dashboard Cite

An efficient and straightforward copper-catalyzed method allowing vinylation of N- or O-nucleophiles with di- or trisubstituted vinyl bromides is reported. The procedure is applicable to a broad range of substrates since N-vinylation of mono-, di-, and triazoles as well as O-vinylation of phenol derivatives can be performed with catalytic amounts of copper iodide and inexpensive nitrogen ligands 3 or 8. In the case of more hindered vinyl bromides, the use of the original bidentate chelator 8 was shown to be more efficient to promote the coupling reactions than our key tetradentate ligand 3. The corresponding N-(1-alkenyl)azoles and alkenyl aryl ethers are obtained in high yields and selectivities under very mild temperature conditions (35-110 degrees C for N-vinylation reactions and 50-80 degrees C for O-vinylation reactions). Moreover, to our knowledge, this method is the first example of a copper-catalyzed vinylation of various azoles. Finally, this protocol, practical on a laboratory scale and easily adaptable to an industrial scale, is very competitive compared to the existing methods that allow the synthesis of such compounds.

show abstract

Palladium catalysed aryl enol ether synthesis from vinyl triflatesElectronic supplementary information (ESI) available: experimental. See http://www.rsc.org/suppdata/cc/b3/b307574e/

Abstract: Vinyl triflates can be efficiently converted into the corresponding aryl enol ethers by treatment with a phenol, NaO(t)Bu and a catalyst generated from Pd2dba3 and 2-(di-(t)Bu-phosphino)biphenyl.

Cited by 39 publications

References 15 publications

A One Pot Transition‐Metal‐Free Synthesis of Styrenyl Ethers from 2‐Aryloxy/Alkoxy Acetophenones

A One Pot Transition‐Metal‐Free Synthesis of Styrenyl Ethers from 2‐Aryloxy/Alkoxy Acetophenones

Methods for Vinyl Ether Synthesis

Mild Copper‐Catalyzed Vinylation Reactions of Azoles and Phenols with Vinyl Bromides

Contact Info

Product

Resources

About